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Live Music: Gina Sobel

Matt Palmieri Country Music

Join us from 2:30–5:30 PM as Matt Palmieri brings his distinctive country sound to Fallen Tree. He’s one of our favorites.

Music Provided by Blue Ridge School

Live music provided by Blue Ridge School at Hark Vineyards, Earlysville.

Chili Night with Live Music: John Kelly

Kick off the weekend with us! Just 5 miles from the Downtown Mall, join us for a celebration of Virginia oysters and wine every Friday night this season. Pair your oysters with a glass of sparkling Blanc de Blancs or enjoy our many other food options paired with a variety of gold medal winning wines. We also offer juice flights and cheese boards for the kids. There is something for the whole family at Eastwood. Live music by John Kelly, 5-8PM.

Live Music: Andy Tichenor

Andy Tichenor live in the beer garden at Brewing Tree Beer Company, Afton.

Friday Cheers with Keith McFaden

Join us every Friday night for live music 5:30-8 and fried seafood specials!

GootGenuG Live

Organically grown jazz fusion quartet

Outdoor Movie Night: Kelly's Heroes

An evening under the stars at Horton Vineyards with a screening of the classic film Kelly's Heroes. Bring a blanket or lawn chair and settle in for a relaxed night among the vines. Popcorn and milkshakes available for purchase. Starts 5:30 PM. Free admission.

Don’t Look Up with Sweet Jane’s Kitchen – crab cake food truck

Elevate your Friday plans with the fantastic sounds of DON’T LOOK UP! Featuring Andy Burdetsky (bass/vocals), Dave Sherman (guitar/vocals), Rob Martin (guitar/vocals), and Lance Foster (drums/vocals). Don’t Look Up will have everyone rocking to their awesome Americana music that’s deeply rooted in the Blues! Friday, November 6th, from 6 to 8:30pm. Open to all. No cover.

Friday Sunset Soirée - The Inclinators with Two Brothers Southwestern Grill

Friday Sunset Soirée live music with The Inclinators, food by Two Brothers Southwestern Grill.

Hazy Mountain Harvest Table

A table set for autumn. Five courses move from persimmon and goat cheese, through acorn squash and autumn vegetables, to Chateaubriand with garlic parsnip puree and mashed sweet potato, before ending with spiced panna cotta, poached pear, and maple creme anglaise. Paired wines accompany each course. Ticketed event.

Live Music: South River Strings Band

Member Mingle at Evening Star with Winemaker Maya Hood White

Winemaker Pop-Up: Chris Tropeano

Enjoy free samples and tour the facility with some of our independent winemakers on Fridays at the Virginia Wine Collective!

JRB's Friday Night Jam Session

Weekly Friday night jam session at James River Brewery. Join in and possibly get in the lineup for a paid gig.

NOVEMBER trivia WITH TAG TEAM ENTERTAINMENT

November Trivia night with Tag Team Entertainment at Hazy Mountain.

Steve Lanza Jr. and Friends Live at Patch

Steve Lanza Jr. and Friends Live at Patch at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Whiskey Glasses: A Tribute to Morgan Wallen

WHISKEY GLASSES NASHVILLE THE HITS OF MORGAN WALLEN Calling all Morgan Wallen fans — Whiskey Glasses Nashville is coming to The Foundry! Featuring Adam James backed by a powerhouse band of Nashville professional musicians, Whiskey Glasses Nashville brings the songs, sound, and energy of one of country music’s biggest stars to the stage. From the massive hits to the fan favorites you know every word to, get ready for a full night of Morgan Wallen music LIVE at The Foundry. FRIDAY, NOVEMBER 6, 2026 Doors: 7:30 PM GA Standing — $19 Seating — $29 Showroom Balcony -- $39 ALL AGES — Under 18 with an adult The Foundry at Basic City Beer Co. Waynesboro, VA Grab your tickets early — especially if you want a seat! Genre: Country Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

Apple Harvest Festival

Vintage Virginia Apples and the CoveGarden Ruritan Club invite you to the 26th annual Apple Harvest Festival at Albemarle CiderWorks.

Blue Ridge Mountain Maze Corn Maze & Fall Festival

Blue Toad Hard Cider presents the Blue Ridge Mountain Maze fall festival: 5-acre corn maze ('A-Maze-ing Catch'), giant mountain slides, farm animals, pumpkins, apple sling shot, night maze, food trucks and Blue Toad cider on tap. Admission $16 ($15 age 12 & under).

Sip & Savor Express Train Ride

Scenic round-trip train ride from Louisa station with guided tasting of four estate wines and artisan charcuterie board.

Bark Market & Pet Portraits

One of Oakencroft's favorite days of the year returns! Come meet adoptable dogs, shop the Bark Market, and get pet portraits at Oakencroft Farm & Winery.

Norton Showcase – Presented by Norton Network – Grand Norton Tasting

The Norton Showcase – Presented by Norton Network Date: November 7, 2026 | Time: 11:00 AM – 5:00 PM Celebrate Norton, Virginia’s native grape, at the Norton Showcase, presented by Norton Network! This exclusive event brings together Virginia’s premier Norton producers for a day of exceptional wines, great food, live music, and friendly competition. Whether you’re a longtime Norton fan or discovering the varietal for the first time, you’ll enjoy sampling a wide range of Norton wines, meeting the winemakers behind them, and experiencing the passion that makes Virginia’s native grape so special. Grand Norton Tasting Tickets CLICK TO PURCHASE YOUR TICKETS HERE Your Grand Norton Tasting Ticket includes tasting samples from each of the participating wineries. $30 when purchased in advance $40 when purchased at the gate on the day of the event Guests must be 21 years of age or older with a valid government-issued photo ID to purchase or redeem a Grand Norton Tasting Ticket. All IDs will be checked before participating in wine tastings or purchasing wine by the bottle or glass. Event Highlights Grand Norton Tasting featuring Virginia’s top Norton producers Fred Reno Norton Challenge Cup wine competition will be held and the winner announced during the event Meet the winemakers Live music Local food trucks and artisan vendors CLICK TO PURCHASE YOUR TICKETS HERE Please Note No pets allowed. This is an outdoor event. Please dress for the weather. Join us for a day of great wine, delicious food, live entertainment, and a celebration of Virginia’s signature grape! Cost: $30

Salute & Sip: A Military K9 Tribute

In celebration of Veterans Day weekend, a free, family-friendly event supporting the Military Working Dog Team Support Association (MWDTSA). Sip Horton wine on the grounds while learning about the bond between military working dogs and their handlers, with K9 trainer Austin Bodine and retired military working dog Bali Y499. 10% of all sales that day go to MWDTSA. Free admission, no tickets required. 11 AM - 4:30 PM.

Grilled Cheese & Beer Pairing

Saturday grilled cheese and beer pairing at WildManDan Brewery. Only 12 seats available; tickets required (21+ only).

Live Music: Jim Richardson

Come see Jim Richardson! Jim will be playing from 12:30-3:30PM.

Andrew Hill

Live Music: Bill & John

Live music 1-4 PM at Afton Mountain Vineyards. Tasting room open 11-6 PM.

Taste of Nelson: In the Corn Maze

Sip and stroll the corn maze with unlimited tastings from cideries, breweries and wineries along Nelson 151, plus two live bands, food trucks and a souvenir glass. VIP entry at 1 PM; general admission 2-6 PM. Early bird GA $44, VIP $79.

Wings Over Wine Country

Food Truck: Canelo's Burritos

Canelo's Burritos food truck at Starr Hill Brewery in Crozet, 2-10 PM.

Joyful Bauble Co. Pop-Up

We’re excited to welcome Joyful Bauble Co., a Charlottesville-based handmade jewelry brand, to Fallen Tree Vineyard. Created by Katherine, Joyful Bauble Co. features whimsical, unique pieces made with polymer clay and brass.

Live Music: Keith Bryant

Live music from Keith Bryant from 2-5pm at The Barn at 678. Enjoy wine, flights, beer, cider and mead on the porch. No outside beverages.

Live Music: Kiz Carter (Trio)

Music in the Mountains by Mike Proffitt

Come on out and join us on this beautiful fall afternoon! We’ll have great live music by Mike Proffitt Choose your favorite DuCard wine and sit back while you listen to music. Lite noshing menu of local fare available or bring your own picnic.

Wine Tasting & Live Music: Michael Wayne Dill

Wine tasting and live music by Michael Wayne Dill in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

The Sounds of Erynn McLeod

Erynn McLeod performs from 2:30–5:30 PM, delivering soft, atmospheric acoustic music perfect for an easy afternoon.

Rum Punch Jamaican Cuisine - Guest Food Truck

Rum Punch Jamaican Cuisine - Guest Food Truck at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Anthony Semiao Music

Live music by Anthony Semiao at Hark Vineyards, Earlysville.

Shuck & Sip: All You Can Eat Oystah Roast with Oyster Catcher Sea Farms x Stinson Vineyards x Fallen Tree Vineyard

It's Oyster Roast Season! Oyster Catcher Sea Farms brings the classic All You Can Eat Northern Neck "Oystah Roast" to the mountains. $85 includes all you can eat raw and roasted Revival oysters, one glass of Stinson Vineyards or Fallen Tree Vineyard wine, and live music (band TBA). Held at the White Hall Community Building, 2904 Browns Gap Turnpike, Crozet (indoor/outdoor tented, rain or shine). Bring your own shucking knife or buy one at the event. Ticketed event.

kat & the travelers

kat & the travelers return to our slice of paradise here in Free Union. Featuring Kathleen Kraft, Doug Hedstrom, Mike Haag, and John Stubblefield, with their ultra cool “Steel Toe Originals, Roots, Jazzblues, Hot Swing, Vintage Country Rock Folk” sounds. Saturday, November 7th, from 5 to 8pm. Open to all. No cover.

Live Music: Don't Look Up

Lockjaw Classic Rock 🎺 | Eastwood After Dark

Come see Lockjaw! They will be playing from 5-8PM. About Lockjaw: Crowd-pleasing classic rock and blues. Join us for upbeat & fun bands every Saturday night. Gather your friends and family and join us for live music that you’ll want to dance to! Plus sit back and enjoy your favorite beverage and delicious food.

Press Play Music Series: Cake Fight

Modern pop and classic rock you can't help but dance to.

Live Music: Dara James

To start November, Bald Top is bringing one of our favorites to the Tap Barn. Dara James brings the sounds of blues/rock fusion to Madison, mixing the sounds of Stevie Ray Vaughn, Hendrix, and Clapton into his own style. 6-9pm.

Music in the Mountains at the Corn Maze

A-Maze-ing live music Saturday night 6-10pm at Blue Ridge Mountain Maze, presented by Blue Toad Hard Cider, on the last weekend of the fall festival. Blue Toad cider on tap, local craft brews, food trucks.

Valley Street Drifters at Patch Brewing Co.

Live music from Valley Street Drifters at Patch Brewing Co. in Gordonsville.

Slate River Band

FREE SHOW! Slate River Band - 36 years of making "real" country music. Founded in 1989 by Michelle and Nick Nixon with Buddy Amos, the band was revived with their son Trace Nixon in 2018.

Nightfall of Diamonds - Celebrating the Grateful Dead

Nightfall of Diamonds returns to The Foundry at Basic City Beer Co. for another long, strange trip celebrating the music of the Grateful Dead. Ticketed event.

Blue Ridge Mountain Maze Corn Maze & Fall Festival

Blue Toad Hard Cider presents the Blue Ridge Mountain Maze fall festival: 5-acre corn maze ('A-Maze-ing Catch'), giant mountain slides, farm animals, pumpkins, apple sling shot, night maze, food trucks and Blue Toad cider on tap. Admission $16 ($15 age 12 & under).

Smuggler Sunday

Wine club members only specialty flight of library or special release wines.

Bloody Mary & NFL Sunday

Bloody Marys every Sunday with NFL games streaming at 92 Acres!

Chen's Kitchen - Guest Food Truck

Chen's Kitchen - Guest Food Truck at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Mercy Creek Live Music

Live Music: Brian Franke

Come see Brian Franke! Brian will be playing from 1-4PM.

Vinyasa Yoga

Sunday Vinyasa Yoga at Chisholm Vineyards, 1-2 PM. Tickets required.

Cider & Strings: An Afternoon with Tristan Dougherty & the Heart Pines

A Sunday well spent.

Live Music: Melissa Hansen

Live Music: Scuffletown

Music In The Mountains with Acoustic Aubrey

Join us for Music in the Mountains from “Acoustic” Aubrey. Aubrey plays venues all over Virginia, DC, Maryland, and North Carolina and is best known for covers of classic R&B, jazz, acoustic rock, and more. Always a great time at DuCard to sit, relax, and enjoy a fantastic afternoon of music with some great wine. Lite noshing menu is available or bring your own snacks. No cover. Reservations are recommended. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

Music: King Golden Banshee

Music: King Golden Banshee at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Second Sunday Bluegrass Jam

Wine Tasting & Live Music: Michael Wayne Dill

Wine tasting and live music by Michael Wayne Dill in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Irish Music: Aaron Olwell & Friends

Enjoy this energetic and eclectic Irish jam session every 2nd Sunday of the month. Patrick & Aaron Olwell and friends play their fine renditions of traditional tunes all afternoon. Light bites available.

Tai Chi

Tai Chi at The Batesville Market. Tickets via Afton Tickets.

Wine Tasting & Live Music: Steve Michael Smith

Wine tasting and live music by Steve Michael Smith in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Music Bingo

Wine Tasting & Live Music: Steve Michael Smith

Wine tasting and live music by Steve Michael Smith in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Food Truck: PotLucky Cville

Trivia Night

Wine Wednesday – Extended Tasting Room Hours & Food Trucks

Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm every Wednesday! Unwind with a rotating lineup of local food trucks serving from 4:00–7:30pm, then put your knowledge to the test at trivia in the pavilion starting at 6:00pm – with King Family Vineyards gift cards up for grabs. Our Wine Wednesday series runs from early March through the end of November, giving you plenty of opportunities to enjoy sunsets with us on the farm!

How Might We Wednesdays

Bring the thing that's bugging you. Every Wednesday from 5 to 7 PM, write your problem on a card at the bar and pin it to the board; the room picks one and spends two hours working on it together. Not a talk and not a demo, an actual go at something a neighbor is stuck on. Hosted by The Smithy.

Run, Walk, Crawl Club

Weekly Run, Walk, Crawl Club every Wednesday at 6 PM at WildManDan Brewery (21+ only).

Simply Flamazing Paint Night

Trivia Night at Patch

Karaoke Night

Join us for karaoke night at the Virginia Wine Collective in the loft! Grab a drink, bring your friends, and take the mic for a night of fun, music, and great vibes. Karaoke is hosted 7-9PM, the Collective will be open 5-10PM! 21+.

Vinyl Share

Vinyl Share every Thursday 4-7 PM at WildManDan Brewery (21+ only). Bring a record to spin.

Craft Door Mats Workshop

Live Music: The Go-Tos (Grass on the Other Side)

Paint + Sip at the Virginia Wine Collective

Come paint with us, no experience necessary, all materials included! Learn to paint this design step by step. Your ticket includes a canvas, specialty paint, and all supplies; each class is taught by a professional artist who guides you through various techniques at a comfortable pace. One ticket per painter. Beverage NOT included in price.

Trail Run Club

Trivia Night with Mike & Miranda

It's Trivia time!

Trivia Night

Trivia every Thursday 6:30-8:30 PM. Grab your buddies for a fun night of trivia, delicious beers, and hot, artisanal pizza.

Adult Karaoke Night

Open Mic Night

Live Music: Tony Hirtz

Tony Hirtz live in the beer garden at Brewing Tree Beer Company, Afton.

Live Music: Paxton Henderson

Rum Punch Jamaican Cuisine - Guest Food Truck

Chili Night with Live Music: Sue Harlow

Come see Sue Harlow! Sue will be playing from 5-8PM.

Boot Scoot Square Dance Party

YEEHAW, IT'S SQUARE DANCING TIME!!

Friday Cheers with The Mash

Join us every Friday night for live music 5:30-8:30 and fried seafood specials!

An Evening with Dave McIntyre

Ian Gilliam & The FireKings with Canelos Burritos food truck

We’re kicking off the weekend with Ian Gilliam & The FireKings. They’ll be treating us all to their incredible “Blues, Rockabilly, Honky Tonk, and Rock & Roll music” live inside the cozy confines of our tropical oasis. Friday, November 13th, from 6 to 8:30pm. No cover. Open to all.

Winemaker Pop-Up: Jake Busching + Dogwood & Thistle

Enjoy free samples and tour the facility with independent winemakers Jake Busching and Dogwood & Thistle at the Virginia Wine Collective!

JRB's Friday Night Jam Session

Friday Night Jam Session at 6:30 PM at James River Brewery. Join us and possibly get in the lineup for a paid gig!

Steve Lanza Jr. and Friends Live at Patch

Don't Look Up

The Honky-Tonk Heathens

The Honky Tonk Heathens are back! After bringing the good times to the Basic City Taproom Terrace, The Honky Tonk Heathens make their debut on The Foundry stage for a night of live local music.

Silver Starlight Opportunity Ball

Come enjoy a memorable night for a great cause at Afton Mountain Vineyards. All-day listing; see event page for details and tickets.

Sip & Savor Express Train Ride

Scenic round-trip train ride from Louisa station with guided tasting of four estate wines and artisan charcuterie board.

Grilled Cheese & Beer Pairing

Saturday grilled cheese and beer pairing at WildManDan Brewery. Only 12 seats available; tickets required (21+ only).

East End Fair

Join us for a day-long celebration of Virginia country life, inspired by the grand countryside fairs of the UK. Enjoy tastings from local wineries, breweries, and distilleries, live music, field sports, artisan vendors, and more — all set against the rustic beauty of Keswick horse country. Held at East End Farm, 292 Hamilton Rd, Louisa, VA. More info: https://www.smvwines.com/east-end-fair

Pizza by Blue Ridge Pizza Co.

Blue Ridge Pizza Co. serving pizza at 92 Acres.

Live Music: Porch Dogs

Come see the Porch Dogs! They will be playing from 12:30-3:30PM. About Porch Dogs Porch Dogs Keith and Everette have been entertaining Central and Southwest Virginia for over seven years with a variety of music from mellow to rocking. Pop, Rock, Americana, Soul, Country and Oldies. These dogs do it all!

Live Music: Ty Burkhardt

Live music 1-4 PM at Afton Mountain Vineyards. Tasting room open 11-6 PM.

Food Truck: Canelo's Burritos

Canelo's Burritos food truck at Starr Hill Brewery in Crozet, 2-10 PM.

Georgian Wine Celebration

Horton Vineyards, in collaboration with the Georgian Embassy, showcases Georgian grape varietals grown right here in Virginia. Pouring: Horton Vineyards, Montifalco Vineyard, House Strunk Winemaking, Cave Ridge Vineyard, Fables & Feathers Winery and Stinson Vineyards. Tickets $28.52/pp.

Live Music: Dara James

Music in the Mountains by Scuffletown

Come out and join us Saturday afternoon for the rollicking live music by Scuffletown! Your favorite wine is available for pairing with the yummy eats from our lite noshing menu. Sit back and enjoy it all while you listen to Marc’s smooth-as-the-cab-franc voice and Johnny’s multi-instrumental accompaniments. There’s something for everyone, so come join the fun! No cover. Reservations are recommended and can be made here. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

Paint + Sip at 92 Acres

Come paint & sip with us! No experience necessary, all materials included! Hosted by Blue Ridge Brushes. Ticketed event – buy tickets on Eventbrite.

Wine Tasting & Live Music: Matt Palmieri

Wine tasting and live music by Matt Palmieri in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Live Music in the Orchard: The Pollocks

The Pollocks are led by Jason Pollock, former guitarist and songwriter for Seven Mary Three, who penned hits such as "Cumbersome" and "Water's Edge".

Live Music with Brian Franke

From 2:30–5:30 PM, Brian Franke takes the stage with classic rock favorites that pair perfectly with a glass of wine and a laid-back afternoon.

The Art of Wine

An event supporting The Arc of Piedmont, showcasing artwork from The Arc Studio paired with wines from Grace Estate. Pop in any time between 4 & 7 PM to enjoy mountain views, wine tastings, artwork, and artmaking.

Cider Smackdown 2026: The Single Varietal Showdown

Join Albemarle CiderWorks for an evening of cider tasting, charcuterie, and conversation with cider enthusiasts and makers from across Virginia in the 2026 Cider Smackdown: The Single Varietal Showdown.

Live Music: The Loya Brothers

Perennial Collection

We are delighted to have Perennial Collection returning to our tropical oasis! “Featuring female led vocal covers of R&B, Soul, Hip-Hop, and Jazz! Perennial Collection delivers dynamic vocal harmonies and jazz-infused arrangements to please the ear and move your feet.” Saturday, November 14th, from 5 to 8pm. Open to all. No cover.

The Wavelength 🎺 | Eastwood After Dark

Join us for upbeat & fun bands every Saturday night. Gather your friends and family and join us for live music that you’ll want to dance to! Plus sit back and enjoy your favorite beverage and delicious food.

Buzzard Hollow Boys Live

Dustbowl meets Delta Blues

Crown Club Saturday: Murder Mystery Party

Crown Club members and guests are invited to solve Chiswell's murder mystery, starting at 5:30 PM on Saturday, November 14.

Live Music: Rich Ridgell

Blending bluegrass, folk, and country into a unique blend of Americana, multi-instrumentalist Rich Ridgell takes the Tap Barn stage 6-9pm.

NCCF Silver Starlight Ball

A magical evening at Veritas celebrating the 25th anniversary of the Nelson County Community Fund (NCCF). Music, dancing, and a three-course dinner paired with fine wine, plus a live auction with Ken Farmer of PBS's Antiques Roadshow and a silent auction of regional experiences. 6:30 PM - 11:45 PM. Cocktail or formal attire; silver sparkles encouraged. Proceeds support NCCF's work in food access, housing security, education, youth development, and health across Nelson County. Tickets $250+.

Groove Revolution

Free show! Groove Revolution brings a high-energy, funky set designed to fill the dance floor at Pro Re Nata in Crozet.

Mama Tried

Truffle Feast

A four-course wine paired feast prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $270 per person, all-inclusive.

The Soaring Eagles - A Musical Salute to The Eagles

THE SOARING EAGLES — A MUSICAL SALUTE TO THE EAGLES LIVE AT THE FOUNDRY Saturday, November 14th, 2026 Doors: 6:30 PM | Showtime: 8:00 PM WAYNESBORO — Get ready for a night celebrating the timeless music of one of the greatest American rock bands of all time. The Soaring Eagles – A Musical Salute to the Eagles are coming to The Foundry at Basic City Beer Co. on Saturday, November 14th, bringing the unmistakable harmonies, guitar work, and legendary songs of the Eagles to our stage. From the laid-back California country-rock of the early years to the arena-sized hits that made the Eagles one of the best-selling bands in music history, The Soaring Eagles deliver a live tribute built for longtime fans. Sing along to favorites like “Take It Easy,” “Peaceful Easy Feeling,” “One of These Nights,” “Life in the Fast Lane,” “Desperado,” “Heartache Tonight,” and, of course, “Hotel California.” It’s an evening of classic songs, soaring harmonies, and the soundtrack of a generation — performed live in the intimate concert setting of The Foundry. All Ages - Under 18 with an Adult The Foundry at Basic City Beer Co. 1010 E. Main Street Waynesboro, VA Tickets on sale now. Genre: Classic Rock Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

Heirloom Apple Tasting

Of course, you've heard of Granny Smith and Red Delicious, but what about Esopus Spitzenburg and Belle de Boskoop? At Albemarle CiderWorks, we cultivate over 250 unique apple varieties. Join us for a guided heirloom apple tasting.

Paint Your Pet Autumn Workshop

Local artist Anissa Frantz sketches your pet on an 11x14 canvas from a photo you send two weeks ahead, then teaches you to paint the portrait. All materials provided; $60/ticket.

Bloody Mary & NFL Sunday

Bloody Marys every Sunday with NFL games streaming at 92 Acres!

Books and Brews

Truffle Lunch

A four-course wine paired feast prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $270 per person, all-inclusive.

Live Music: Forde Upshur

Vinyasa Yoga

Sunday Vinyasa Yoga at Chisholm Vineyards, 1-2 PM. Tickets required.

Alex Caton & Friends: Trad Irish Music

Armchair Expedition Viognier 2pm

Often called Virginia’s signature white grape, Viognier is deeply rooted in Virginia soil. But where did it come from? How do different terroirs and vinification practices affect its aromas and flavors? Join us to discover the answers. An aromatic beauty, Viognier is the only grape permitted in the Northern Rhône application of Condrieu. Viognier is also the most-planted white Rhone varietal in the US and produces a full bodied wine with intense aromatics of peach, apricot, honeysuckle and rose. In this class, we will taste old and new world examples and see how terroir influences what ends up in our glasses. This session will be at 2pm. Small bites will accompany the wines, and wines will be available for purchase at the end of the session. Session price: $49 per person (Wine Club discounts apply, Email Beth for WC reservations), advance reservation required, and space is limited. Purchase tickets by clicking HERE Check out an article about these world of wine events here Cost: $49

Live Music: Alex Arbaugh

Live Music: Matty & Mirabelle

LUA Project Live

A new style of traditional music inspired by the sounds and sones of Mexico, Appalachia, and the Atlantic Basin

Music Bingo

Everyone loves singing along with their favorite songs and who doesn’t love a competitive game of Bingo? Music Bingo brings together the best of both worlds for a high energy game that is fun for everyone. Simply listen to your favorite music, match the songs to the titles on your music bingo cards, and win great prizes!

Ron Gentry Music

Live music by Ron Gentry at Hark Vineyards, Earlysville.

Wavelength with Special Guest Bob Bennetta

Legendary jazz pianist Bob Bennetta joins the trio for an afternoon of blues and jazz, and will also be doing lead vocals! Sam Green – bass, Larry Bisgaier – guitar/vocals, Waverly Milor – harmonica/vocals. Sunday, November 15, from 2 to 5pm. Open to all. No cover.

Wine Tasting & Live Music: Little Walter & The Convictions

Wine tasting and live music by Little Walter & The Convictions in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Artist Reception: Ellen Copeland

Meet the artist! Ellen Copeland will be in the Loving Cup Tasting Room Gallery to discuss the large-format abstract oils in her exhibit "Color and Comfort in Hang Time" (on view Oct 2 – Dec 13). Sip a glass of certified-organic wine and enjoy a Sunday afternoon with art.

Latin Dance Social with Bachata Flow

Dance your way through the rest of 2026 at The Foundry! Latin dance social with Bachata Flow - whether you're an experienced dancer or you've never stepped onto the dance floor, everyone is welcome. Ticketed event.

Wine Tasting & Live Music: Steve Michael Smith

Wine tasting and live music by Steve Michael Smith in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Music Bingo

Fletcher Daniel

Wine Tasting & Live Music: Steve Michael Smith

Wine tasting and live music by Steve Michael Smith in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Food Truck: PotLucky Cville

Trivia Night

Steal the Glass

The third Wednesday of every month, take home a souvenir glass with a draft purchase! Check out our social media for this month's glass.

Willie De Live Music

Wine Wednesday – Extended Tasting Room Hours & Food Trucks

Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm every Wednesday! Unwind with a rotating lineup of local food trucks serving from 4:00–7:30pm, then put your knowledge to the test at trivia in the pavilion starting at 6:00pm – with King Family Vineyards gift cards up for grabs. Our Wine Wednesday series runs from early March through the end of November, giving you plenty of opportunities to enjoy sunsets with us on the farm!

How Might We Wednesdays

Bring the thing that's bugging you. Every Wednesday from 5 to 7 PM, write your problem on a card at the bar and pin it to the board; the room picks one and spends two hours working on it together. Not a talk and not a demo, an actual go at something a neighbor is stuck on. Hosted by The Smithy.

Run, Walk, Crawl Club

Run, Walk, Crawl Club every Wednesday at 6 PM at WildManDan Brewery, Afton. 21+ only.

Trivia Night at Patch

Wreath Making Workshops @ The Market

Holiday wreath making workshops at The Market at Grelen, November 19-20 (more sessions Nov 21-22). Ticketed event - please pre-register. Session times not listed on the calendar.

Vinyl Share

Vinyl Share every Thursday 4-7 PM at WildManDan Brewery, Afton - bring a record to spin. 21+ only.

Mahjong with Mountain Mahj

Beginner-friendly Mahjong lessons with Mountain Mahj: learn the rules, strategies, and traditions of the game in easy-to-follow steps while hanging out with friends. Lesson is 2.5 hours. Ticketed event (mountainmahjczt.com/classes).

Trail Run Club

Candlelight Sound Bath

A restorative evening sound bath by candlelight in the Center at Oakencroft. $34 per ticket.

Trivia Night

Trivia every Thursday 6:30-8:30 PM. Grab your buddies for a fun night of trivia, delicious beers, and hot, artisanal pizza.

Karen's Line Dancing

Line Dancing with Hometown Line Dancing

Waynesboro, it’s time to kick up some dust. Join Hometown Line Dancing at The Foundry at Basic City Beer Co. for a night of country music, dancing, and good times. Whether you're a seasoned dancer or stepping onto the floor for the very first time, everyone is welcome.

Next Stop Comedy (Tickets Required)

Live Music: Dara James

Dara James live in the beer garden at Brewing Tree Beer Company, Afton.

Catchin Fish' and Chips Food Truck

Catchin’ Fish & Chips serves up wild-caught Alaskan cod, hand-battered and fried golden to order alongside crispy fries and flavorful sauces. Stop by the truck for a fresh, satisfying take on the classic seaside favorite.

Paxton Henderson — Modern Bluegrass & Singer-Songwriter

Enjoy an afternoon with Paxton Henderson from 4:30–7:30 PM, featuring modern bluegrass and singer-songwriter selections.

Chili Night with Live Music: Matthew O’Donnell

Come see Matthew O’Donnell! Matthew will be playing from 5-8PM.

Library Wine Deep Dive

Join us for a special Library Deep Dive tasting as we open the cellar and revisit some of our favorite older vintages. This is a unique opportunity to taste wines from our library, discover how they’ve evolved with age, and enjoy a few bottles that rarely make an appearance. We will focus each session on a single wine. Seating is limited, and advance reservations are required. A limited number of bottles will be available for purchase after the tasting. Cost is $ 32 per person – pay at the event. Make your reservation today! Come sip, savor, and take a little journey through the years with us! Cost: $32

Friday Cheers with Alex Arbaugh

Join us every Friday for live, local music from 5:30-8:30 with no cover charge!

Tara Mills Band Live

Blend of folk, bluegrass, and Americana

Ken Farmer & The Authenticators with Carrie’s Soul Food food truck

Join us in the tropics of Free Union for a priceless night of rocking good fun featuring Ken Farmer & The Authenticators (Ken Farmer, Rob Martin, Preston Wallech, Frank Cain). Carrie’s Soul Food food truck onsite from 5:30pm. Friday, November 20th, from 6 to 8:30pm. Open to all. No cover.

Paint & Sip

Come paint with us!

Winemaker Pop-Up: Josh Cataldo

Enjoy free samples and tour the facility with some of our independent winemakers on Fridays at the Virginia Wine Collective!

JRB's Friday Night Jam Session

Friday Night Jam Session at 6:30 PM at James River Brewery. Join us and possibly get in the lineup for a paid gig!

Steve Lanza Jr. and Friends Live at Patch

The Foundry Rocks with Spiral Fracture, I Am The Liquor & Raised By Sheep

The Foundry turns it up with a full night of heavy local and regional rock featuring Spiral Fracture, I Am The Liquor, and Raised By Sheep. Three bands take the stage for a night of loud guitars, heavy riffs, and high-energy live music.

Holiday Marketplace @ The Depot

Holiday Marketplace at the Grelen Depot, 10AM-4PM.

Bulk Juice Sale [Heirloom Cider-Apples]

Calling all home cidermakers - grab your carboys! We're crushing heirloom apple varieties for bulk unpasteurized juice, blended specifically for cider making.

Craft Sublime Artisan Fair

The Craft Sublime Artisan Fair returns to The Foundry at Basic City Beer Co., 11 AM–4 PM. Free admission, family friendly. Where creativity meets community!

Oysters + Wine

Salty Bottom Blue Oysters serves fresh Virginia oysters, raw or grilled, at Michael Shaps Wineworks. Grab a glass or bottle of Michael Shaps wine and settle in. No reservation required. Raw oysters also available to pre-order for the holidays.

Live Music: Heidi Riddell

Come see Heidi Riddell! Heidi will be playing from 12:30-3:30PM.

BRIMS & VINO HAT WORKSHOP

Hat making workshop with wine at Hazy Mountain Vineyards.

Live Music: Michael Bergamo

Live music 1-4 PM at Afton Mountain Vineyards. Tasting room open 11-6 PM.

Live Music: Jon Spear Band

Music In The Mountains with Bomar & Ritter

Join us for an afternoon of good wine and music with the duo of Mary Bomar and Bob Ritter. Bomar & Ritter are excellent singers, songwriters, and guitarists that play original folk/pop. Grab a glass or bottle of your favorite wine and relax while listening to these two amazing artists. Plus the view couldn’t be better! No cover. Reservations are recommended. Make yours here. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

Wine Tasting & Live Music: Doc Campbell

Wine tasting and live music by Doc Campbell in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Ken Harrington — Solo Acoustic

Ken Harrington delivers solo acoustic takes on classic rock favorites everyone knows and loves. From 2:30–5:30 PM, he takes the stage with stripped-down arrangements, easy rhythms, and plenty of sing-along moments. It’s the kind of set that feels instantly familiar and effortlessly fun.

Live Music in the Orchard: Mojo Pie

Grab a glass and join us for live music by Mojo Pie! Mojo Pie was created when Susan Munson invited Frank Bechter to a songwriters workshop, and they've been bringing harmonies to wineries ever since.

180 Band

Live music by 180 Band at Hark Vineyards, Earlysville.

Beleza 🎺 | Eastwood After Dark

Join us for upbeat & fun bands every Saturday night. Gather your friends and family and join us for live music that you’ll want to dance to! Plus sit back and enjoy your favorite beverage and delicious food.

Joel Streeter and Chad Page (of Boxed Lunch) with TJJ Island Catering food truck

Joel Streeter and Chad Page of Boxed Lunch bring their high-energy acoustic music to the GHW&B stage for the first time as a duo, covering The Beatles, Paul Simon, and The Grateful Dead alongside Joel’s originals. Saturday, November 21st, from 5 to 8pm. Open to all. No cover.

Live Music: Kurt Crandall

Nightfall of Diamonds: Grateful Dead Jams Live

Let there be songs to fill the air...

Live Music: Keith Bryant

Chart-topping singer/songwriter Keith Bryant, a seminal figure in the local music community, plays originals plus classic country, rock, and folk tunes. 6-9pm.

The Loya Brothers Live at Patch

The Nashville Nights Band: The Ultimate 90's Country Experience

THE NASHVILLE NIGHTS BAND: THE ULTIMATE 90'S COUNTRY EXPERIENCE IS BACK! After coming incredibly close to SELLING OUT The Foundry last time, The Nashville Nights Band returns to Basic City Beer Co. on Saturday, November 21st for another huge night celebrating the greatest era of country music! If you were here last time, you know what kind of party this is. The dance floor was packed, the crowd was singing along, and the room was nearly full. Now they're coming back — and we're expecting an even bigger night. The Nashville Nights Band: The Ultimate 90's Country Experience brings you a full night of the country hits that defined a generation. Break out the boots and hats, round up your crew, and get ready to sing and dance to the songs that made '90s country unforgettable. Saturday, November 21st, 2026 The Foundry at Basic City Beer Co. Waynesboro, VA Doors: 6:30 PM Show: 8:00 PM ALL AGES - UNDER 18 WITH AN ADULT SEATING SELLS FAST! Our seated ticket options are always some of the first to go for Nashville Nights, so if you want a seat, don't wait until show week to grab your tickets. Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

Holiday Marketplace @ The Depot

Holiday Marketplace at the Grelen Depot, 10AM-4PM.

Heart of Virginia Artisans "giving thanks" MARKET

Giving Thanks artisan market at Hazy Mountain Vineyards.

Oysters in the Library

Freshly Shucked and Oysters Rockefeller from 11:00am-4:00pm

Bloody Mary & NFL Sunday

Bloody Marys every Sunday with NFL games streaming at 92 Acres!

Vincent Zorn Live Music

Wreath Making Workshop

Sip, create, and get into the holiday spirit at our workshop where you can make your very own one of a kind festive wreath! Ticketed event.

Chiswell Book Club November Meeting

Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!

Holiday Wreath-Making Workshop

A festive afternoon of wreath-making with Bellair Farm at Michael Shaps Wineworks. Create a natural holiday wreath from locally sourced evergreens, pinecones, dried wildflowers and botanicals. All materials included; no experience needed. $75 per person; advance reservations required.

Live Music: FarAway

Come see FarAway! FarAway will be playing from 1-4PM on the stage in The Barn.

UVA Planetarium Constellation Tours

Come learn about the stars and planets from the Dark Skies, Bright Kids (DSBK) portable planetarium! Constellation tours, traveling to the center of the universe, and more.

Grapevine Wreath Making Workshop

An afternoon of wine and wreaths in the Party Barn. All wreath-making supplies plus your first glass of wine included ($60). Bring materials from your own garden, gloves and pruners if you like.

Music in the Mountains with Pat Anderson

The mountains are calling and so is the music by Pat Anderson – an Oklahoma-born, Virginia-raised singer-songwriter. Pat’s a roots rocker with a strong affinity for Dylan, Springsteen, and Petty and possessed with the tough-minded country-rock sensibility of Todd Snider. We are thrilled to have him share his talents with us here at DuCard Vineyards. Bring along snacks or select eats from our lite noshing menu while you take in the rhythm and views! No cover. Reservations are recommended and can be made here. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

Old Time String Band Jam

Wine Tasting & Live Music: Jacob Paul Allen

Wine tasting and live music by Jacob Paul Allen in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

BRIMS Ceol agus Céilí: Irish Session & Social Dance

Let's Dance!

Special Private Screening: Immigrant Grapes: Odyssey of Forbidden Wines by Lucie Morton

Join us at 5:30 PM on Sunday, November 22 for a special private screening of Immigrant Grapes: Odyssey of Forbidden Wines, a new film by viticulturist, author and now filmmaker Lucie Morton. The film follows her personal quest to bring the Cunningham grape back to its ancestral home on her family’s farm in Tidewater Virginia. This fascinating journey includes grapevine science, politics, intrigue and romance. Her odyssey took her across the US and across the Atlantic to the Azores, Madeira Island, the Cevennes Mountains of France, and southern Brazil. As Lucy ultimately becomes successful in repatriating Cunningham to Virginia, it will join Norton, which we have planted at DuCard and use for our Norton varietal wine, our C’est Trop port-style wine and the fun and funky Dorothy’s Slippers rosé, as the only other surviving Virginia native grape. And yes, DuCard Norton will be available to sip while enjoying the film. Tickets are $10 and can be paid at the door. Space is limited so please make your reservations by emailing Beth at beth@ducardvineyards.com Cost: $10

Wine Tasting & Live Music: Steve Michael Smith

Wine tasting and live music by Steve Michael Smith in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Music Bingo

Wine Tasting & Live Music: Steve Michael Smith

Wine tasting and live music by Steve Michael Smith in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Food Truck: PotLucky Cville

Beer & Board Games

Trivia Night

Thanksgiving Eve Gathering

Kick off Thanksgiving at Eastwood! Join us the Wednesday before Thanksgiving for live music, delicious oysters from Salty Bottom Blue, and a glass of your favorite Eastwood wine. Enjoy fresh oysters on-site or pick up your Thanksgiving oyster preorder.

Wine Wednesday – Extended Tasting Room Hours & Food Trucks

Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm every Wednesday! Unwind with a rotating lineup of local food trucks serving from 4:00–7:30pm, then put your knowledge to the test at trivia in the pavilion starting at 6:00pm – with King Family Vineyards gift cards up for grabs. Our Wine Wednesday series runs from early March through the end of November, giving you plenty of opportunities to enjoy sunsets with us on the farm!

How Might We Wednesdays

Bring the thing that's bugging you. Every Wednesday from 5 to 7, the room picks one problem a neighbour is stuck on and works it together. Write yours on a card at the bar and pin it to the board. Hosted by The Smithy.

Run, Walk, Crawl Club

Run, Walk, Crawl Club every Wednesday at 6 PM at WildManDan Brewery, Afton. 21+ only.

Trivia Night at Patch

JACKYL

JACKYL Returns to The Foundry at Basic City Beer Co. Wednesday, November 25, 2026 | Thanksgiving Eve JACKYL is coming back to Waynesboro for a special Thanksgiving Eve concert at The Foundry at Basic City Beer Co. Known for a live show that is loud, unpredictable, and unmistakably Jackyl, the Georgia-based rock band has spent more than three decades building a reputation as one of American rock and roll’s most relentless touring acts. Formed in the early 1990s, Jackyl exploded onto the national rock scene with its self-titled debut album, delivering songs including “Down on Me,” “When Will It Rain,” “I Stand Alone,” and the band’s signature anthem, “The Lumberjack.” Led by frontman Jesse James Dupree, Jackyl has remained a road-tested staple of hard rock and Southern rock ever since, earning a fiercely loyal fanbase through decades of touring and an anything-can-happen approach to the stage. This Thanksgiving Eve, Jackyl returns to The Foundry for a night built for fans who would rather start the holiday weekend with loud guitars, cold beer, and a chainsaw than spend Wednesday night sitting in traffic. Genre: Hard Rock Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

Thanksgiving Celebration Lunch (Sold Out)

A four-course feast prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $105 per person for the meal. $140 per person for the meal with wine pairings (+9.3% tax & 22% service charge).

Trail Run Club

Black Friday @ The Market - Christmas Tree Sales Begin

Black Friday at The Market at Grelen, 10AM-4PM. Christmas tree sales begin!

Visit with Santa @ The Market

Visit with Santa at The Market at Grelen, 11AM-2PM.

Black Friday Music featuring Wavelength

Black Friday Music featuring Wavelength at Merrie Mill Farm & Vineyard, 1 PM to 4 PM.

Black Friday Music In The Mountains with South Canal Street

Bring your Thanksgiving guests and your dancing shoes and come out to DuCard for the fun and fabulous music of South Canal Street! They bring their repertoire of your favorites including songs by The Beatles, Chicago, Motown, Eagles and top hits from the golden era of music, late 1950’s to the 1970’s! Grab your favorite DuCard wine and have some fun! Hungry? We’ve got a great noshing menu to select from or bring your own snacks. No cover. Reservations are recommended and can be made here. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

Live Music: The Loya Brothers

The Loya Brothers live in the beer garden at Brewing Tree Beer Company, Afton.

Live Music: The Bob & Kenn Duo

Black Friday live music. With a unique blend of guitar and mandolin, The Bob & Kenn Duo play a variety of music genres.

Paint & Sip "Winter Woods" with Blue Ridge Brushes

Come paint with Blue Ridge Brushes at Hazy Mountain Vineyards! Design: "Winter Woods". Instructor: Catelyn. Your ticket includes all painting materials and an 11x14 canvas. Step-by-step instruction from a professional artist, no experience necessary. Ticketed event.

Chili Night 🫘

Warm up your Friday nights with Chili Night at Eastwood: every Friday 5–8 p.m., hearty chili, homemade cornbread and all the fixings, with meat and vegetarian options. Enjoy wine, games and music. Full menu also available.

NOVEMBER BACHATA

Sunset Salsa Bachata night in November at Hazy Mountain.

Friday Cheers with Ben Reade

Live music and fish fry specials every Friday 5:30-8:30!

Karaoke Party

Your Friday night plans are made.

Live Music: Greg Ward

Midnight Buzz with Special Guest Brian Franke with Jones Catering food truck

A post-Thanksgiving Friday night with Midnight Buzz and special guest Brian Franke, playing acoustic and electric classic rock covering the Allman Brothers, Tom Petty, Steve Miller, Joni Mitchell, Fleetwood Mac, Linda Ronstadt, and more. Friday, November 27th, from 6 to 8:30pm. Open to all. No cover.

JRB's Friday Night Jam Session

Friday Night Jam Session at 6:30 PM at James River Brewery. Join us and possibly get in the lineup for a paid gig!

Sun-Dried Opossum with John Shenk

BLACK FRIDAY AT THE FOUNDRY — SUN DRIED OPOSSUM RETURNS! Get out of the stores and spend Black Friday with some live music! Sun Dried Opossum takes over The Foundry stage on Friday, November 27th, with special guest John Shenk for a FREE night of live music at Basic City Beer Co. Friday, November 27th Doors: 6:30 PM Show: 8:00 PM The Foundry at Basic City Beer Co. Waynesboro, VA FREE SHOW ALL AGES Guests under 18 must be accompanied by an adult. Proper ID required. Grab some dinner, grab a beer, and trade the Black Friday madness for a night of live music at The Foundry. Genre: Rock

Holiday Marketplace @ The Depot

Holiday Marketplace at the Grelen Depot over Thanksgiving weekend (times not listed; other marketplace days run 10AM-4PM).

The Toader: Thanksgiving Weekend Race for the Underachiever

A 'challenging' 1.51 km race across the 27-acre Blue Toad farm with three rest stops: a pint of 'Into the Orchard' cider, a fresh cider donut, and a slice of hot bacon. After-party in the Cider Hall with a local band, a Small Business Saturday market and a food truck. Participants get a custom Toader t-shirt, wristband and headband. Ticketed; start time not listed on the site.

Visit with Santa @ The Market

Visit with Santa at The Market at Grelen, 11AM-2PM.

Live Music: Lenny Burridge

Come see Lenny Burridge! Lenny will be playing from 12:30-3:30PM.

Live Music: Nicholas Darden

Live music 1-4 PM at Afton Mountain Vineyards. Tasting room open 11-6 PM.

Mini Maker’s Holiday Market

Eastwood Farm and Winery is hosting our first-ever Young Makers Market on Saturday, November 28 — featuring kid and teen artisan vendors selling handmade goods just in time for the holidays!

Live Music: Bryan Horowitz

Live Music: James Tamelcoff

Live music from James Tamelcoff from 2-5pm at The Barn at 678. Enjoy wine, flights, beer, cider and mead on the porch. No outside beverages.

Music In The Mountains with Grass Fed

Come out to the foothills of the Blue Ridge and spend your afternoon at DuCard Vineyards listening to live music from Grass Fed. This amazing group plays a mix of funk, rock and roll, and reggae. Choose your favorite bottle of DuCard wine, add a snack from our lite noshing menu and enjoy the beautiful mountain scenery to complete the day! No cover. Reservations are recommended and can be made here. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

Wine Tasting & Live Music: Jimmy Baranik

Wine tasting and live music by Jimmy Baranik in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Live Music in the Orchard: Her Checkered Past

Come share a cider with friends. Enjoy live music by Her Checkered Past with Anne O'Brien and Frank Bechter in the orchard.

Pancho Country Music

Pancho brings a full, boots-on-the-ground country sound—big hooks, big heart, and plenty of twang.

Jackson, Pendergrass & Townsend 🎺 | Eastwood After Dark

Join us for upbeat & fun bands every Saturday night. Gather your friends and family and join us for live music that you’ll want to dance to! Plus sit back and enjoy your favorite beverage and delicious food.

The Pollocks Live

Jason Pollock, Thomas Gunn, Maryline Meyer, Nathan West, Randy Mendicino

Live Music: Tommy Wood

Authentic classic country storytelling from Ruckersville's own Tommy Wood, drawing inspiration from Merle Haggard and George Jones. 6-9pm.

Blake Hunter & The Gatherers

Karaoke Night

Line Dancing with Hometown Line Dancing

Waynesboro, it’s time to kick up some dust. Join Hometown Line Dancing at The Foundry at Basic City Beer Co. for a night of country music, dancing, and good times. Whether you're a seasoned dancer or stepping onto the floor for the very first time, everyone is welcome.

Holiday Marketplace @ The Depot

Holiday Marketplace at the Grelen Depot over Thanksgiving weekend (times not listed; other marketplace days run 10AM-4PM).

Visit with Santa @ The Market

Visit with Santa at The Market at Grelen, 11AM-2PM.

Bloody Mary & NFL Sunday

Bloody Marys every Sunday with NFL games streaming at 92 Acres, 12-6 PM.

Paint & Sip

Come paint with us, no experience necessary, all materials included! Instructor: Catelyn. Ticket includes all painting materials and an 11×14 canvas. Ticketed event.

Grapevine Wreath Making Workshop

An afternoon of wine and wreaths in the Party Barn. All wreath-making supplies plus your first glass of wine included ($60). Bring materials from your own garden, gloves and pruners if you like.

Holiday Wreath Workshop & Wine

Join Hope Henderson of Flora Design for a holiday wreath-making afternoon with Oakencroft wine. $90 per ticket.

Music Bingo

Everyone loves singing along with their favorite songs and who doesn’t love a competitive game of Bingo? Music Bingo brings together the best of both worlds for a high energy game that is fun for everyone. Simply listen to your favorite music, match the songs to the titles on your music bingo cards, and win great prizes!

Sun V Set Live

Indie folk artist based in Richmond, VA

Vinyl Day at the Vineyard

We’re dusting off the turntable and bringing in our favorite LP’s for Vinyl Day at DuCard Vineyards. Dig out the old record albums and bring them along for an afternoon of listening, sharing, and reminiscing. We can’t wait to hear all of your favorites while we share ours. There will be wine, of course and our light noshing menu is available while you sit and enjoy. No better way to spend the afternoon. Catch you on the flip side! Reservations recommended. No cover.

Virginia Rieley & Eliza Evans – Artist Meet & Show

Join us in the tasting room at Blenheim Vineyards and meet the artists, Virginia Rieley & Eliza Evans, Sunday, November 29th from 2-4pm. Their artwork will be on display and available for purchase. We will have snacks and wine for sale by the glass, bottle, and flights. Eliza Evans & Virginia Rieley grew up in North Garden near Charlottesville and have been friends since childhood, collaborating artistically for over 35 years. Eliza paints acrylic portraits from life, usually in a single sitting; Virginia is a mixed media collage artist who combines her own photography with watercolor and pen to create layered scenes of local places. Together they co-create the hand-drawn Every Day is a Holiday Calendar, self-published each year since 2006.

Wine Tasting & Live Music: Jimmy Cherry

Wine tasting and live music by Jimmy Cherry in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Latin Dance Social with Bachata Flow

Dance your way through the rest of 2026 at The Foundry! Latin dance social with Bachata Flow - whether you're an experienced dancer or you've never stepped onto the dance floor, everyone is welcome. Ticketed event.

Wine Tasting & Live Music: Steve Michael Smith

Wine tasting and live music by Steve Michael Smith in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Wine Tasting & Live Music: Steve Michael Smith

Wine tasting and live music by Steve Michael Smith in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Wreath Workshops @ The Market

Holiday wreath workshops at The Market at Grelen, December 2-5. Ticketed event - please pre-register. Session times not listed on the calendar.

How Might We Wednesdays

Bring the thing that's bugging you. Every Wednesday from 5 to 7, the room picks one problem a neighbour is stuck on and works it together. Write yours on a card at the bar and pin it to the board. Hosted by The Smithy.

Run, Walk, Crawl Club

Run, Walk, Crawl Club every Wednesday at 6 PM at WildManDan Brewery, Afton. 21+ only.

Karaoke Night

Join us for karaoke night at the Virginia Wine Collective in the loft! Grab a drink, bring your friends, and take the mic for a night of fun, music, and great vibes. Karaoke is hosted 7-9PM, the Collective will be open 5-10PM!

Vinyl Share

Vinyl Share every Thursday 4-7 PM at WildManDan Brewery, Afton - bring a record to spin. 21+ only.

Sip, Style, Graze: The Art of Building a Charcuterie Board w/ Caperberries & Co

Learn the art of building a charcuterie board with Caperberries & Co at the Grelen Depot, 6-9PM. Ticketed event - please pre-register.

Trivia Night

Trivia every Thursday from 6:30 - 8:30 pm at Bald Top Brewing Co.

Line Dancing with Hometown Line Dancing

Waynesboro, it’s time to kick up some dust. Join Hometown Line Dancing at The Foundry at Basic City Beer Co. for a night of country music, dancing, and good times. Whether you're a seasoned dancer or stepping onto the floor for the very first time, everyone is welcome.

Chili Night 🫘

Warm up your Friday nights with Chili Night at Eastwood: every Friday 5–8 p.m., hearty chili, homemade cornbread and all the fixings, with meat and vegetarian options. Enjoy wine, games and music. Full menu also available.

DECEMBER trivia WITH TAG TEAM ENTERTAINMENT

December Trivia night with Tag Team Entertainment at Hazy Mountain.

JRB's Friday Night Jam Session

Friday Night Jam Session at 6:30 PM at James River Brewery. Join us and possibly get in the lineup for a paid gig!

2026 Concealed Darkness Release Party & Oyster Fest

Darkness is coming! Release of the 2026 Dark Hollow Reserve, Concealed Darkness, paired with oysters: Oyster Catcher Sea Farms of White Stone, VA on site with raw and grilled oysters, plus fried oysters, Brunswick Stew and the regular menu from Blue Mountain Barrel House Restaurant.

Blooms4Good Wreath Making Workshop

Holiday wreath making workshop with Blooms4Good at Merrie Mill Farm & Vineyard, held the morning of the Annual Holiday Market. Ticketed - purchase tickets via the event page.

Visit with Santa @ The Market

Visit with Santa at The Market at Grelen, 11AM-2PM.

Annual Holiday Market

Annual Holiday Market at Merrie Mill Farm & Vineyard, 11:30 AM to 5 PM.

Port Tasting at Horton Vineyards

The Wine Vault is open! Celebrate 30 years of Port at Horton Vineyards with a drop-in tasting in the climate-controlled Wine Vault: vintage Ports spanning 1995-2020 alongside Courage Port, plus Port-style dessert wines Pear Dessert, Bone Orchard, and About Face. Light charcuterie provided. 11:30 AM - 4:00 PM. Ticketed event (limited to 150, ages 21+, non-refundable unless cancelled). Dress warmly. Regular tasting room service is separate.

Holiday Market

Holiday Market with vendors, kids crafts, local wine & more. Food trucks: Hog and Hooch & Nothing Bundt Cake. Live music: Fiona & Marie, 1:30-4pm.

Holiday Carols: Brian Franke 🎁

Come see Brian Franke! Brian will be playing from 12:30-3:30PM.

Live Music: Moon Glow

Live music 1-4 PM at Afton Mountain Vineyards. Tasting room open 11-6 PM.

Live Music: Dara James

Live Music: South Canal Street

Live music from South Canal Street from 2-5pm at The Barn at 678. Enjoy wine, flights, beer, cider and mead on the porch. No outside beverages.

Music in the Mountains with Pat Anderson

The mountains are calling and so is the music by Pat Anderson – an Oklahoma-born, Virginia-raised singer-songwriter. Pat’s a roots rocker with a strong affinity for Dylan, Springsteen, and Petty and possessed of the tough-minded country-rock sensibility of Todd Snider. We are thrilled to have him share his talents with us here at DuCard Vineyards. Bring along a picnic or select eats from our noshing menu while you take in the rhythm and views! No cover. Reservations are recommended and can be made here. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

Wine Tasting & Live Music: Ty Burkhardt

Wine tasting and live music by Ty Burkhardt in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Live Music in the Orchard: ZuZu's Hot 5

Join us for an afternoon of live music. Zuzu's Hot 5 is Pete Vigour (swing guitar), Doug Bethel (trombone), Brandon Rose (trumpet), Sam Green (upright bass) and more.

DECEMBER BACHATA

Sunset Salsa Bachata night in December at Hazy Mountain.

Pamela Ryder & Mighty Fine Company 🎺 | Eastwood After Dark

Come see Pamela Ryder & Mighty Fine Company! They will be playing from 5-8PM. Join us for upbeat & fun bands every Saturday night.

Private Showing of We the Wine People – a feature documentary

Join us at DuCard Vineyards for a special private showing of a film about Virginia Wine on December 5, 2026 at 5:30pm. Purchase your tickets HERE WE THE WINE PEOPLE is a feature documentary about Virginia wine and the people turning a complex region into one of America’s most compelling wine stories. Moving from Blue Ridge vineyards to coastal farms, blind tastings, harvest celebrations, barrel rooms, and tasting rooms, the film follows the growers, winemakers, educators, organizers, and advocates who are building a regional identity together. More than a wine film, it is a story about land, belonging, resilience, hospitality, and the belief that a rising tide lifts all boats. Directed and produced by Greek-born filmmaker and wine storyteller Chrisa Giorgi, the film travels through vineyards, barrel rooms, tasting rooms, blind tastings, and harvest gatherings to reveal Virginia as a state that is made up of regions where winemaking is defined by collaboration, resilience, history, and place. Wine will be available for purchase by the bottle or glass. The price is $25 and space is limited to 100 so purchase your tickets now. A share of the proceeds go to fund filmmaker’s post-production costs. Purchase your tickets HERE Sorry, no wine club member discounts for this event. Cost: $25

The Octagon Dinner

A four-course wine paired feast featuring older, rare vintages of Octagon. Prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $270 per person, all-inclusive.

Visit with Santa @ The Market

Visit with Santa at The Market at Grelen, 11AM-2PM.

Bloody Mary & NFL Sunday

Bloody Marys every Sunday with NFL games streaming at 92 Acres, 12-6 PM.

Food Truck: Rum Punch

Originally from Jamaica, Chef Racquel White has become an integral part of the Charlottesville community, serving authentic Jamaican food from the Rum Punch food truck.

Max Mandu Live Music

Santa Is Coming To Town

Join us for a special visit from Santa! Plus, holiday milk and cookies flights are back by popular demand for the kids. Indoor event with opportunities to take your own photos with Santa. No cost to visit Santa.

The Octagon Lunch

A four-course wine paired feast featuring older, rare vintages of Octagon. Prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $270 per person, all-inclusive.

Silent Book Club

Sip cider and read in quiet camaraderie. No assigned reading, no obligations. Bring your own book of choice. A free social event hosted in the Orchard Room, now the first Sunday of each month.

Wine Tasting & Live Music: Mark Dunn

Wine tasting and live music by Mark Dunn in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore. Special hours 1-4 PM.

Holiday Food & Wine Pairing with Tassie Pippert

Join Emmy-winning creator, chef, and host of the PBS series Un-Wine'd and Tassie's Table, Tassie Pippert, for a fun tasting and conversation about holiday food and DuCard wine pairings. Tassie will share some of the foods and wines that grace her holiday table, and each guest will leave with recipes ready for the season. Session begins at 2pm. Tickets $49 per person; reservations required in advance. Wine club member discount applies.

Wine Tasting & Live Music: Steve Michael Smith

Wine tasting and live music by Steve Michael Smith in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Wine Tasting & Live Music: Steve Michael Smith

Wine tasting and live music by Steve Michael Smith in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

How Might We Wednesdays

Bring the thing that's bugging you. Every Wednesday from 5 to 7, the room picks one problem and works it together. Write yours on a card at the bar and pin it to the board. Not a talk and not a demo, an actual go at something a neighbour is stuck on. Hosted by The Smithy.

Run, Walk, Crawl Club

Run, Walk, Crawl Club meets every Wednesday at 6 PM at WildManDan Brewery. 21+ only.

Vinyl Share

Vinyl Share every Thursday 4-7 PM at WildManDan Brewery - bring your records. 21+ only.

Mahjong with Mountain Mahj

Beginner-friendly Mahjong lessons with Mountain Mahj: learn the rules, strategies, and traditions of the game in easy-to-follow steps while hanging out with friends. Lesson is 2.5 hours. Ticketed event (mountainmahjczt.com/classes).

Music Bingo

Everyone loves singing along with their favorite songs and who doesn’t love a competitive game of Bingo? Music Bingo brings together the best of both worlds for a high energy game that is fun for everyone. Simply listen to your favorite music, match the songs to the titles on your music bingo cards, and win great prizes!

Trivia Night

Trivia every Thursday from 6:30 - 8:30 pm at Bald Top Brewing Co.

Open Mic Night

Chili Night with Live Music: John Kelly

Come see John Kelly! John Kelly will be playing from 5-8PM.

Library Wine Deep Dive

Join us for a special Library Deep Dive tasting as we open the cellar and revisit some of our favorite older vintages. This is a unique opportunity to taste wines from our library, discover how they’ve evolved with age, and enjoy a few bottles that rarely make an appearance. We will focus each session on a single wine. Seating is limited, and advance reservations are required. A limited number of bottles will be available for purchase after the tasting. Cost is $ 32 per person – pay at the event. Make your reservation today! Come sip, savor, and take a little journey through the years with us! Cost: $32

Winemaker Pop-Up: Chris Tropeano

Enjoy free samples and tour the facility with some of our independent winemakers on Fridays at the Virginia Wine Collective!

JRB's Friday Night Jam Session

Friday Night Jam Session at 6:30 PM at James River Brewery. Join us and possibly get in the lineup for a paid gig!

Brandon Wayne & His Lonesome Drifters

Last Illusion: A Tribute to Trans-Siberian Orchestra

LAST ILLUSION: A TRIBUTE TO TRANS-SIBERIAN ORCHESTRA Friday, December 11th Doors: 6:30 PM | Show: 8:00 PM Experience the sights, sounds, and magic of the holiday season as Last Illusion brings the music and spectacle of Trans-Siberian Orchestra to The Foundry! Based in Roanoke, Virginia, Last Illusion delivers a powerful tribute to TSO, combining soaring vocals, orchestral arrangements, hard-rock guitars, and theatrical production into an unforgettable live experience. From the dramatic instrumentals to the larger-than-life Christmas classics, Last Illusion captures the energy and excitement that have made Trans-Siberian Orchestra a holiday tradition for generations. Fans may also hear selections from Savatage, whose music and members played an important role in the origins of TSO. Bring the family and celebrate the season with a night of incredible musicianship, rock & roll, and Christmas magic. All Ages — Under 18 with adult The Foundry at Basic City Beer Co. 1010 E. Main Street | Waynesboro, VA Genre: Tribute Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

Holiday Marketplace @ The Depot

Holiday Marketplace at the Grelen Depot, 10AM-4PM.

Visit with Santa @ The Market

Visit with Santa at The Market at Grelen, 11AM-2PM.

Holiday Market

Browse local vendors, enjoy delicious food and drinks, sip on milk and cookie flights, and soak up the holiday spirit with live music! Market 12-4PM; Holiday Carols 12:30-3:30PM.

Holiday Carols: Sharif 🎁

Get festive and listen to holiday carols by Sharif! Sharif will be playing from 12:30-3:30PM.

Live Music: Porch Dogs

Live music 1-4 PM at Afton Mountain Vineyards. Tasting room open 11-6 PM.

Wreath Workshop @ The Market

Holiday wreath workshop at The Market at Grelen, 1PM. Ticketed event - please pre-register.

Joyful Bauble Co. Pop-Up

We’re excited to welcome Joyful Bauble Co., a Charlottesville-based handmade jewelry brand, to Fallen Tree Vineyard. Created by Katherine, Joyful Bauble Co. features whimsical, unique pieces made with polymer clay and brass.

Live Music: Jim O'Ferrell

Live music from Jimmy O from 2-5pm at The Barn at 678. Enjoy wine, flights, beer, cider and mead on the porch. No outside beverages.

Music in the Mountains with Jimmy O

Spend a beautiful winter afternoon relaxing at the winery and listening to the music of Jimmy O. He is an amazing guitarist with an unique style of classic rock, oldies, and a rockin’ country mix that’s sure to please everyone! Just add a bottle of wine, some great Virginia views, and you’ve set your weekend off to a great start! A light noshing menu is available to accompany your wine. No cover. Reservations are recommended and can be made here. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

Paint + Sip at 92 Acres

Come paint & sip with us! No experience necessary, all materials included! Hosted by Blue Ridge Brushes. Ticketed event – buy tickets on Eventbrite.

Wine Tasting & Live Music: Little Walter & The Convictions

Wine tasting and live music by Little Walter & The Convictions in the barn at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Ten varietals to explore.

Live Music in the Orchard: Wavelength

Enjoy live music by The Wavelength! A consortium of Charlottesville's finest musicians led by vocalist/harmonica Waverly Milor, performing vintage rock, blues and originals.

Holiday Wreath Workshop w/ The Freckled Flower Farm

Live Music: Jon Spear Band