Charlottesville Wine CountryWhat's on this weekend

Spark Studio Permanent Jewelry Pop-Up

Join us as we welcome Spark Studio to Fallen Tree Vineyard for a permanent jewelry pop-up. Spark Studio specializes in custom-fitted, clasp-free jewelry, including bracelets, anklets, rings, and necklaces, available in options like sterling silver, gold-filled, and 14k solid gold.

Twisted Oak BBQ Food Truck

Twisted Oak Barbecue, Charlottesville’s premier craft BBQ trailer known for its Texas-style smoked brisket, ribs, pulled pork, savory sides, and house-made banana pudding, is rolling into Fallen Tree Vineyard!

Live Music: Chris Hammock

Live Music with Brian Franke: Classic Rock Favorites

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.

Zuzu's Hot 5 with SwingCville Live

Live Music: Tidewater Valley

Friday Night Out with John Kelly

Wind down at DuCard with a wine flight, and entertainment after the long work week with the music of John Kelly. He is a long-time local musician, writer, and producer who has worked with many other artists from the area, as well as various national artists. He brings along his rock-solid guitar playing and singing, rooted in traditional and country styles. We’ll have wine flights for 1/2 price beginning at 4pm. Grab a snack from our noshing menu or bring your own picnic and settle in for a relaxing great time! No cover. Reservations are recommended. Make yours here today.

Friday Sundowner's Music featuring Bailey Hayes

Friday Sundowner's Music Series featuring Bailey Hayes at Merrie Mill Farm & Vineyard, 5 PM to 9 PM.

Virginia Oyster & Wine Celebration with Live Music: Matthew O’Donnell

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 September 4: FarAway | 5-8PM September 11: John Kelly | 5-8PM September 18: Matthew O’Donnell | 5-8PM September 25: Sue Harlow | 5-8PM October 2: Eli Cook | 5-8PM October 9: John Kelly | 5-8PM October 16: Matthew O’Donnell | 5-8PM October 23: Matthew O’Donnell | 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 Creek Mill Grass

Live music 5:30-8 and fried seafood specials at Blue Mountain Barrel House.

Music Bingo

Now starting at 6 PM! Music Bingo Night with Tag Team Entertainment (the crew behind Wine Down Trivia Nights and Friday Night Karaoke) — the perfect blend of music, games, and wine, set against a gorgeous sunset. Bring your friends and grab a glass.

Live Music: South River Strings Band

Sunset Soirée - Chickenhead Blues with Twisted Provisions

Friday Sunset Soirée live music with Chickenhead Blues, food by Twisted Provisions.

Harvest Nights at the Collective + Winemaker Pop-Up: Joy Ting

Experience Virginia wine country during its most exciting season. Join us on Friday evenings throughout harvest for a behind-the-scenes look at what happens when grapes begin their journey to becoming wine. Also tonight: Winemaker Pop-Up with Joy Ting — free samples and a facility tour with one of the Collective's independent winemakers.

Barbara Martin/Liz Barnes Band with Carrie's Soul Food Truck

Jazz/blues music by the Barbara Martin/Liz Barnes Band (Liz Barnes – piano, Barbara Martin – vocals, Tom Harbeck – bass, Jim Howe – drums), performing live inside the tropical glass conservatory. Friday, October 16th, 6 to 8:30pm. Open to all. No cover. Carrie's Soul Food food truck will be onsite with service beginning at 5:30pm. Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

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.

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.

Scuffletown Duo!

The Greenhorns @ Pro Re Nata

Free show. The Greenhorns, a 7-piece Charlottesville band, bring a blend of New Orleans funk, jump blues, R&B and jazz to Pro Re Nata Brewpub & Music Hall in Crozet. Drinks and dinner available from the Taproom Table.

Ciders & Screams Movie Night: Ghostbusters

Fireside Collective

Fireside Collective returns to The Foundry at Basic City Beer Co. on Friday, October 16th, bringing their high-energy blend of bluegrass, Americana, folk, and roots music back to Waynesboro for an unforgettable night. Known for their electrifying live performances, tight musicianship, and fearless improvisation, Fireside Collective seamlessly weaves traditional bluegrass with modern influences, creating a sound that is both deeply rooted and refreshingly original. Expect soaring harmonies, blazing instrumentals, and a show packed with energy from start to finish!! Doors: 6:30 PM Show: 8:00 PM All Ages (under 18 must be accompanied by an adult) Genre: Jamgrass Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

Pumpkin Decorating Workshop

Potting-bar style pumpkin decorating workshop: pick a pumpkin, choose succulents, cacti or terrarium plants, and Grelen's plant experts guide you step by step. $10 ticket includes instruction, soil, moss and dried flowers; pumpkin and plants priced a la carte. Limited to 12 people.

Lecture: Fall Color at Grelen (Free)

A free class highlighting trees and shrubs with vibrant autumn color available now at the Grelen Nursery, which thrive locally, and how to choose the best ones for your landscape. RSVP requested.

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).

Fall Foliage Fest

Grilled Cheese & Beer Pairing

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

Horton on the Go: Town Point Virginia Fall Wine Festival

Horton on the Go: find Horton Vineyards at the 38th Annual Town Point Virginia Fall Wine Festival, Saturday & Sunday, October 17-18, 2026, at Town Point Park on the Downtown Norfolk Waterfront (113 Waterside Drive, Norfolk). More than 25 of the Commonwealth's top wineries pour over 200 wines. Off-site event; all-day listing on Horton's calendar.

Meetin on the Mountain: British Car Show

The Shenandoah Valley British Car Club brings classic British cars to Afton Mountain Vineyards, with food trucks and vineyard views. Tasting room open 11am–7:30pm.

Harvest Party Oyster Roast

Raise a glass of award-winning Eastwood wine to harvest season! Join us at Eastwood Farm and Winery on Saturday, October 17, for our Harvest Party Oyster Roast, part of a celebration of Virginia wine across the Commonwealth. Gather your friends, sip your favorite Eastwood wines, and enjoy a special menu by Salty Bottom Blue, featuring oysters Rockefeller, crab cakes, grilled oysters, and oysters raw on the half shell. Eastwood’s full menu will also be available all day, from 12–7:30 PM. Make a day of it with live music by Heidi Riddell from 12:30–3:30 PM and The Wavelength from 5–8 PM! It’s a day to celebrate the season and the people, places, and flavors that make Virginia wine special.

Live Music: Heidi Riddell

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

Live Music – Soul Shakers

This Southern Soul Horn Band brings the perfect blend of smooth rhythms and electrifying horns that will have you grooving all day long. Whether you’re a fan of classic soul or funky beats, The Soul Shakers are here to deliver an unforgettable experience. Come hungry Barrel and Board will be open serving charcuterie, sandwiches and much more!

Music in the Mountains with Pat Anderson

The mountains are calling and so is the music by singer-songwriter Pat Anderson. 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 a picnic 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.

Live Music with Rebecca Romano

Talented local artist Rebecca Romano performs for an afternoon of music with award-winning Valley Road Vineyards wine. Bring a picnic or grab a pizza, baguette and cheese.

Live Music: The Peacemakers

Live music featuring The Peacemakers at Woodbrook Farm Vineyard. Sip Woodbrook wines and take in the views; Barry Long will be serving BBQ.

An Afternoon with Sue Harlow

From 2:30–5:30 PM, Sue Harlow brings a roots-inspired sound shaped by heartfelt lyrics and classic influences.

Live Music in the Orchard: Alex Caton & Jordan Perry

Alex Caton and Jordan Perry love to sing together. Alex plays fiddle and Jordan guitar, and between the two of them they find themselves in all kinds of musical settings. Live music in the orchard at Albemarle CiderWorks.

Live Music: Bluzonia

Live Music: The Crybabies

The Crybabies perform live at Afton Mountain Vineyards, with food trucks on site. Tasting room open 11am–7:30pm.

Sunset Music Series: Zuzu's Hot 5 + Crozet Seafood

Free sunset live music with Zuzu's Hot 5, plus the Crozet Seafood food truck. No reservations on music nights; bring a chair or blanket. Wines by the glass and bottle, Potter's hard cider by the can.

Live Music: Greg Ward

The Inclinators

The Inclinators make their Glass House Winery & Brewery debut on the conservatory stage. This high-energy quartet is known for a "danceable, soulful sound that blends a timeless spirit of the past with modern twist echoing the warmth of vinyl." Saturday, October 17th, 5 to 8pm. Open to all. No cover. Drew Lambert – Lead Vocals, Chris Yung – Guitar/Vocals, James Grimm – Bass/Vocals, Paul McDaniel – Drums. Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

Matthew O’Donnell Music

Live music from Matthew O’Donnell in the Hark Vineyards tasting room, with estate-grown, Governor's Cup gold medal wines.

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. Saturday Night Music Lineup: September 5: Transatlantic Invasion | 5-8PM September 12: LockJaw | 5-8PM September 19: The Wavelength | 5-8PM September 26: Kat & The Travelers | 5-8PM October 3: The Unsuitables | 5-8PM October 10: Jason Burke: Bunch O’Mugs | 5-8PM October 17: The Wavelength | 5-8PM October 24: Classic Road | 5-8PM Check back for more dates this fall!

LUA Project Live

Harvest Party at King Family Vineyards

An Evening with Frank Morgan: Virginia & French Wines Tasting

Frank Morgan guides a comparative tasting of Pollak and French wines exploring Virginia wine's Old World inspiration.

Valerie Smith and Liberty Pike

Live music 6-9 PM. It's fall in the Blue Ridge and there's nothing better on the stage than some real Appalachian bluegrass. Liberty Pike has a long history on the bluegrass circuit and they really are the total package: whimsical and upbeat.

Hogfish Live at Patch

Hogfish Live at Patch at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Music in the Mountains at the Corn Maze

Live music every Saturday night 6-9 PM at the Blue Ridge Mountain Maze at Blue Toad Hard Cider (included with maze ticket).

Stage Fright! An Improv Comedy Show

Celebrate spooky season with a night of completely unscripted comedy inspired by audience suggestions at Vinegar Hill Theatre (Lighthouse Studio, 220 W Market St). Featuring members of Goat Rodeo's improv teams Big Head Fight and Billionaire Robot Dogs. $10 advance, $15 at the door.

Four Thirty Four (434) with 21 Gunz & Savage Theory

FOUR THIRTY FOUR (434) RETURNS TO THE FOUNDRY with 21 Gunz & Savage Theory Saturday, October 17th, 2026 Doors: 6:30 PM | Show: 8:00 PM We’re excited to welcome back our good friends Four Thirty Four (434) to The Foundry at Basic City Beer Co. for another huge night of live rock! If you’ve caught 434 at The Foundry before, you already know what they bring — a high-energy show, heavy guitars, big vocals, and the kind of performance that feels right at home on our stage. Joining them for the night are 21 Gunz and Savage Theory, rounding out a three-band lineup built for fans who like their rock loud and live. Come early, grab a beer, and get ready for a loud one. Genre: Hard Rock Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

Autumn Plein Air at Grelen

Autumn plein air painting at The Market at Grelen. Registration is closed. (No time listed on Grelen's website.)

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).

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.

Gina Sobel Live Music

Live Music with Rachael Karpo

Rachael is a New Jersey Native and an Air Force Veteran is a soloist who pours her heart into every note she sings. From 80’s and 90’s to Classic Rock and Country, Rachael’s unique blend of music adds to her artistry performances. Barrel and Board will be serving sandwiches, salad, charcuterie and much more!

Family Field Day

Bloody Mary & NFL Sunday

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

Fall Family Day & Harvest Party Market

Chen's Kitchen - Guest Food Truck

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

[Food Truck] Rum Punch

Originally from Jamaica, Chef Racquel White has become an integral part of the Charlottesville community, introducing locals to authentic Jamaican cuisine. Rum Punch food truck on site at Albemarle CiderWorks.

Exclusive DuCard Vineyards & Estate at Meander Gold Medal Experience

Join DuCard Vineyards and The Estate at Meander for an intimate autumn experience celebrating award-winning Virginia wine, seasonal farm-to-table dining, and historic countryside hospitality. Your Journey begins at 12:00 PM at DuCard Vineyards, bordering Shenandoah National Park at the western edge of Madison County. Personally hosted by the Owner, enjoy DuCard’s Gold Medal Wine Flights & Vineyard Tour with special pours of its gold medal winning wines presented in crystal glassware and accompanied by light bites and conversation. Walk the vineyard rows to discover the care and techniques behind DuCard’s wines, then explore the winery and barrel room. A seated tasting offers a special opportunity to sample wines still aging in oak and learn how they develop before bottling. A second tasting session will feature sparkling wines, with samples both from DuCard and around the world. Following the experience, make the approximately 30-minute drive to The Estate at Meander. Settle into your suite or cottage if staying overnight, then gather for our signature four-course Table Experience dinner in the historic Manor House. Your $299-per-person experience includes: DuCard’s private wine tastings Vineyard and winery tour A bottle of The Reverend wine – a special Bordeaux-style blend crafted in ode to Meander’s original builder – awaiting in your room or presented at Meander to take home The Estate at Meander’s signature four-course Table Experience dinner at the Harvest & Hearth Bistro Complimentary Estate breakfast for overnight guests Space is limited. Advance reservations are required BOOK YOUR EXPERIENCE HERE Overnight accommodations are available at an additional cost. Participants meet at DuCard and travel onward to Meander; transprotation is not included BOOK YOUR STAY ONLINE or call The Estate at Meander at 540-672-4912. Cost: $299

Sunday Jazz and Blues featuring Whiskey Django

Sunday Jazz and Blues featuring Whiskey Django at Merrie Mill Farm & Vineyard, 1 PM to 4 PM.

Live Music: Forde Upshur

Sunday Session - The Trio

Sunday Session live music with The Trio.

Session Sunday with Robert Jospé Band

Session Sundays continue at Stinson Vineyards with live music on the patio performed by the Robert Jospé Band. Weather permitting; please leave outside alcohol at home.

Vinyasa Yoga

Sunday vinyasa yoga at Chisholm Vineyards. Tickets required.

Live Music: Brian Franke

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

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.

An Lar Traditional Irish Band

Cider & Strings: An Afternoon with Acoustic Union Live

Live Music: Andy Tichenor

Armchair Expedition - Sparkling Wine

Sparkling wine is not just for special occasions, it can be an everyday drink of choice. There are several methods to make sparking wine across history which are well known or may have just come back in fashion. Now is a time to discover a’ Pet Nat’ or understand what the ‘traditional method’ really means. Is this regional or local? Join us to sip and discuss with sparkling wines from around the world. The 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: Joel Streeter

Alex Caton & Friends: Trad Irish Music

Alex Caton & Friends: Trad Irish Music at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Music on the Deck: Michael Mulvaney

Join us for music on the deck from 2-5pm with Michael Mulvaney

Game Night

Game Night every Monday at 92 Acres – bring your own game or play one of ours!

Music Bingo

Music Bingo at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Fletcher Daniel

Spooky Halloween Trivia

Halloween-themed Monday trivia at Three Notch'd Charlottesville, 7-9 PM. Free to play.

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 Blue Mountain's social media for this month's glass.

Andrew Beverly Live Music

Wine Wednesday – Extended Tasting Room Hours & Food Trucks

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.

Wine Down Wednesday – South Canal Street Band

Enjoy Wednesday evening with Keswick wines, local beers, or a canned cocktails. South Canal Street brings in songs mostly from the 60’s, 70’s and 80’s, including Motown, Funk, Soul, Rock, Pop. Barrel and Board will be serving butter boards, signature sandwiches, and much more!

An Evening of Hope

Evening of Hope: A Community Celebration & Fundraiser October 21, 2026 | 6:00–9:00 PM Eastwood Farm and Winery Join us for Reclaimed Hope’s annual community celebration and fundraiser, where friends, families, and supporters come together for a memorable evening with purpose.

Run, Walk, Crawl Club

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

Trivia Night at Patch

Trivia Night at Patch at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Vinyl Share

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

Porch Nights: Ty Burkhardt ✨

Come see Ty Burkhardt from 5-8PM! Porch Nights at Eastwood ✨ There’s something about a porch at golden hour that makes the world slow down in the best possible way. At Eastwood Farm and Winery, we’re leaning into that feeling all season long with Porch Nights — our weekly Thursday gathering featuring outdoor live music and an easygoing atmosphere. Grab a seat on our covered veranda or at one of our many picnic tables, relax with the sparkly lights overhead, fireflies in the fields, and a glass of porch-sipping wine in hand – join us for your new favorite Thursday tradition.

Trail Run Club

Voodoo Doll Workshop

Paint + Sip at the Virginia Wine Collective

Come paint with us, no experience necessary, all materials included! Your ticket includes a canvas, specialty paint, and all supplies. Each class is taught by a professional artist who will guide you through the design step by step at a comfortable pace. Ticketed event.

Trivia Night with Mike & Miranda

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.

Fresh Pour Thursday

A new beer is tapped at 6:30 PM every Thursday at Three Notch'd Charlottesville, with a free taste.

Karen's Line Dancing (Free, Ages 16+)

Karen's Line Dancing (Free, Ages 16+) at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.