Events in Charlottesville Wine Country

Live Music: Max Mandu at Pippin Hill

Live music with Max Mandu at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

Wine Down Wednesday with The Unsuitables

A night of fantastic music featuring a variety of covers, including Motown, classic rock, and more.

The Front Porch Presents: Jake Blount Band

Ticketed show at Potter's Craft Cider. The Front Porch series features folk and roots music.

Run, Walk, Crawl Club at WildManDan Brewery

Weekly community Run, Walk, Crawl Club meets every Wednesday at 6 PM at WildManDan Brewery in Afton. 21+ only establishment.

Chamber Music Festival Concert

Vinyl Share at WildManDan Brewery

Weekly vinyl record share every Thursday 4-7 PM at WildManDan Brewery. Bring your records and enjoy craft beer. 21+ only.

Porch Nights: Jim Richardson

Game Night! BINGO at Starr Hill Crozet

Join us for everyone's favorite game, BINGO!!!! There will be prizes, laughs and more! With guest host Tyler Rich!

Trail Run Club at Starr Hill Crozet

Join Cville Runners every Thursday at 6pm and take a jaunt on the Crozet Trails! Meet back at our tap room for pints!

Team Trivia

6:30-8 pm. Reservations recommended.

Trivia Night

Trivia every Thursday at Bald Top Brewing Co. Fun night filled with trivia, delicious beers, and hot artisanal pizza!

The Front Porch Presents: Songwriter's Open Mic

Calling all songwriters! An evening of original music at Potter's Craft Cider.

Live Music: Bluzonia

A four-piece band featuring the drummer from the Jon Spear Band. In the beer garden.

Virginia Oyster & Wine Celebration With Live Music

Weekly oyster night featuring fresh oysters, award-winning Virginia wines, and live music. Featuring Matthew O'Donnell.

Friday Night Out with Bomar & Ritter & Half Price Wine Flights

Sit by the stream and breathe in the mountain air while enjoying the musical duo of Mary Bomar and Bob Ritter. They play original folk/pop. Wine flights are half price after 4pm!

Friday Sundowner's Music Series featuring Mercy Creek

Enjoy the Friday Sundowner's music series from 5:30-8:30 PM at Merrie Mill Farm & Vineyard with Mercy Creek.

Tara Mills Band Live

Blend of folk, bluegrass, and Americana at Potter's Craft Cider.

Boozy Trivia Night

Gather your crew and join us for a night of boozy trivia! Grab a cider, bring your smartest teammates, and compete for prizes and bragging rights. Trivia starts at 6:00 PM.

Ken Farmer & The Authenticators

A priceless night of rocking good fun featuring Ken Farmer & The Authenticators. Open to all. No cover.

Paint & Sip "Dark Sunset"

Come paint with us! Ticketed event at Potter's Craft Cider. Tickets on Eventbrite.

Music Bingo Night at Grace Estate Winery

Get ready for Friday night fun at Grace Estate! Music Bingo with Tag Team Entertainment, the same crew behind their popular Wine Down Trivia Nights and Friday Night Karaoke. The perfect blend of music, games, and wine, all set against a gorgeous sunset. Bring your friends, grab a glass, and join us for an unforgettable evening!

The Art of The Low Maintenance Garden & Winter Interest Garden

Free workshop: Learn the art of creating a low maintenance garden and how to build a winter interest garden. Registration required.

Harvest Fest

Second Annual Harvest Fest at Southwest Mountains Vineyards. Celebrate the beauty of harvest time in the Monticello AVA!

Beer & Grilled Cheese Pairing: Oktoberfest Bier

September & October featured pairing: Oktoberfest Bier paired with Local Monastery Gouda, sliced apples, and applebutter on Farmhouse Wheat Bread. Saturdays at 11:30 AM (before the taproom opens). Only 12 seats available — ticketed event, $24.79. Must purchase tickets in advance at SimpleTix.

Bouquet Making Workshop with Blooms4Good

Join us for a floral bouquet workshop using locally sourced flowers from Blooms4Good. Saturday, Sept 19, 12:00-1:00 PM. $60/ticket — 100% of proceeds benefit SARA (Sexual Assault Resource Agency) and International Neighbors in Charlottesville. Food and additional wine available for purchase. Tickets at blooms4good.org.

Live Music – Rixeyville Revival

Come out and rock with the Rixeyville Revival Band — bringing the best hits from the past and present.

Oktoberfest

Oktoberfest at Brewing Tree. Marzen and festbier on the taps, food from the Scratch Kitchen, and the beer garden set up for it.

Oktoberfest | Every Weekend

Oktoberfest celebration running every weekend at Eastwood Farm and Winery.

Oktoberfest

Celebrate Oktoberfest with the Guten Morgen Band (2-5pm), German foods from Chef Roderick, and lots of beer!

Live Music: Heidi Riddell

[InCider Club Members Exclusive] Library Tasting

InCider Exclusive Library Tasting for InCider Club Members. Members-only event.

Harvest Fest Grape Stomp

Grab a slot for the grape stomp — the highlight of Harvest Fest! A little messy, a lot of fun, and a great way to get in the spirit of the season. Tickets required.

Music in the Mountains with Kat and the Travelers

Come bask in the views and enjoy the lively music of Kat and the Travelers. The band plays an awesome blend of originals, swing, vintage jazz, blues, and boogie!

Live Music in the Orchard: The La Da Das

The LaDaDas are three friends and seasoned folksingers performing live in the orchard.

Live Music: Andrew Beverly

Live Music by Tucker Wyatt 3-5pm

Join us at Blenheim Vineyards on Saturday, September 19 from 3–5 PM for an afternoon of free live music with Tucker Wyatt. Settle in under the tent overlooking the vineyard, grab a glass or bottle of Blenheim wine, and spend an easy fall afternoon enjoying live music, good company, and vineyard views. Free admission | No reservations required.

Catching Fish & Chips & Mercy Creek Music

A fun Saturday afternoon combining fresh fish & chips with live music by Mercy Creek. 4:00-7:00 p.m.

The Wavelength | Eastwood After Dark

Live music and dancing every Saturday night at The Barn. Featuring The Wavelength.

Midnight Buzz

Midnight Buzz returns with their eclectic blend of acoustic and electric classic rock covering Allman Brothers, Tom Petty, Steve Miller, Joni Mitchell, Fleetwood Mac, Linda Ronstadt, and more.

Michael Clem & Rusty Speidel Live

Grab a cider and stay awhile as Michael Clem & Rusty Speidel perform live at Potter's Craft Cider.

Live Music: The Rivanna Band

Hailing from VA, the Rivanna Band brings a mixture of rock, country, and indie music that they have carefully curated themselves. Expect some originals thrown in along the way.

Back to Cool Improv Night

Hot on the heels of Hot Improv Summer, Goat Rodeo is back at Vinegar Hill Theatre with 90 minutes of improv comedy that will make you forget vacation’s over! Every show is different, made up on the spot! $10 advance ($15 at the door).

Let's Get Rocked: Def Leppard Tribute w/ Megan Van Halen

An electrifying tribute to Def Leppard featuring Megan Van Halen at Pro Re Nata Brewpub & Music Hall in Crozet, VA.

Live Music with Rachael Karpo

Rachael is a New Jersey Native and Air Force Veteran, a soloist who pours her heart into every performance.

Paint & Sip: Hydrangea Wine Glass

Paint & Sip event with Blue Ridge Brushes at Eastwood Farm and Winery. Paint a hydrangea wine glass while enjoying wine.

Family Field Day

Sunday afternoon on the meadow for the whole crew. Yard games, the scavenger hunt, room to run, and a different featured game each week. Kanjam and Spike Ball are free to borrow at the River Bar.

Live Music: Matty Metcalfe at Pippin Hill

Live music with Matty Metcalfe at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

Oktoberfest | Every Weekend

Oktoberfest celebration running every weekend at Eastwood Farm and Winery.

Oktoberfest

Oktoberfest at Brewing Tree. Marzen and festbier on the taps, food from the Scratch Kitchen, and the beer garden set up for it. Family Field Day runs on the meadow the same afternoon, so bring the kids.

Sunday Blues and Jazz featuring Wavelength

Sunday Blues and Jazz featuring Wavelength, 1:00-4:00 PM at Merrie Mill Farm & Vineyard.

Gabriel Goldstein, Erik "Red" Knierem & Alex Norman Live

Virginia Singer-Songwriters performing original acoustic songs at Potter's Craft Cider.

Live Music: Starfire

Music in the Mountains with Pat Anderson

Singer-songwriter Pat Anderson brings roots rock with a strong affinity for Dylan, Springsteen, and Petty.

Willie DE

Sunday Fun Day featuring Willie DE with his awesome bluesy rock sounds. Open to all. No cover.

Music Bingo

Music Bingo at Eastwood Farm and Winery.

Music on the Deck: Rick Martin

Join us for music on the deck from 2-5pm with Rick Martin.

Food Truck: PotLucky Cville at Starr Hill Crozet

At PotLucky, we specialize in crafting authentic, handmade Chinese steamed buns and dumplings, using traditional recipes with an added southern twist. Our mission is to bring the taste of Asia to Charlottesville, Virginia.

Trivia Night at Starr Hill Crozet

Join us every Tuesday for Trivia! Gather your best team of up to 6 and belly up for your chance to win!

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

Wine Down Wednesday – South Canal Street Band

Enjoy Wednesday evening with Keswick wines, local beers, or canned cocktails. South Canal Street brings great live music to the vineyard.

Run, Walk, Crawl Club at WildManDan Brewery

Weekly community Run, Walk, Crawl Club meets every Wednesday at 6 PM at WildManDan Brewery in Afton. 21+ only establishment.

Vinyl Share at WildManDan Brewery

Weekly vinyl record share every Thursday 4-7 PM at WildManDan Brewery. Bring your records and enjoy craft beer. 21+ only.

Porch Nights: Solo Steve

The Front Porch Presents: Darrell Scott Live

Ticketed show at Potter's Craft Cider. Darrell Scott is a legendary Americana singer-songwriter.

Bold Book Club - Like a Moth to a Flame

Bold Book Club is back! This month: Like a Moth to a Flame by Lillith Abendroth. Bring your copy and your first cider is FREE!

Trail Run Club at Starr Hill Crozet

Join Cville Runners every Thursday at 6pm and take a jaunt on the Crozet Trails! Meet back at our tap room for pints!

Trivia Night

Trivia every Thursday at Bald Top Brewing Co. Fun night filled with trivia, delicious beers, and hot artisanal pizza!

Lockjaw Classic Rock Band

Lockjaw Classic Rock Band returns covering fan favorites spanning the decades from the 60s through the 80s and beyond.

Live Music: Bryan Horowitz

Virginia Oyster & Wine Celebration With Live Music

Weekly oyster night featuring fresh oysters, award-winning Virginia wines, and live music. Featuring Sue Harlow.

Friday Night Out with Acoustic Aubrey and Half Price Wine Flights

Live music from Acoustic Aubrey, best known for covers of classic R&B, jazz, acoustic rock, and more. Half price wine flights after 4pm.

Friday Sundowner's Music Series featuring Johnathan Paige Brown

Enjoy the Friday Sundowner's music series from 5:30-8:30 PM at Merrie Mill Farm & Vineyard with Johnathan Paige Brown.

Pony Show Live

Friday nights are better with live music and cider. Pony Show performs live at Potter's Craft Cider.

Villains Trivia Night

Gather your crew for a night dedicated to all things Villains! Grab a cider, bring your smartest (or most evil) teammates, and compete for prizes and bragging rights.

Veritas Supper Series & Harvest Dinner

The Supper Series concludes its 2026 season with a truffle dinner rooted in Italian cuisine — an elegant, multi-course evening celebrating one of the world's most prized ingredients, thoughtfully paired with Veritas wines. $150 per person, includes wine pairings and service (taxes and fees extra). Wine Club Members receive 20% off first two tickets purchased.

Dinner & a Movie Night

Southwest Mountain's Dinner & A Movie Series is back. Make your reservations today, they are required!

Pumpkin Decorating Workshop

Creative pumpkin decorating workshop at The Market at Grelen. Registration required.

Robert Jospé Trio

Robert Jospé Trio brings high energy, world class jazz.

Chen's Kitchen

Chinese dumplings & fried rice from Chen's Kitchen.

Cheese & Wine Pairing featuring Truckle Cheesemongers

Join Michael Shaps Wineworks for an afternoon of wine and cheese featuring Truckle Cheesemongers of Richmond, Virginia. Explore thoughtfully selected pairings designed to showcase how different cheeses complement and enhance the wines. $70 per person | $60 Wine Club Members. Space is limited and advance reservations are required.

Beer & Grilled Cheese Pairing: Oktoberfest Bier

September & October featured pairing: Oktoberfest Bier paired with Local Monastery Gouda, sliced apples, and applebutter on Farmhouse Wheat Bread. Saturdays at 11:30 AM (before the taproom opens). Only 12 seats available — ticketed event, $24.79. Must purchase tickets in advance at SimpleTix.

Oktoberfest

Oktoberfest at Brewing Tree. Marzen and festbier on the taps, food from the Scratch Kitchen, and the beer garden set up for it.

Oktoberfest | Every Weekend

Oktoberfest celebration running every weekend at Eastwood Farm and Winery.

Fall Seafood Saturday at DuCard with Oysters and Live Music

Nomini Bay Oyster Ranch provides fresh oysters: raw, steamed, grilled, and grilled with toppings. Steamed shrimp available too. $12 entry.

Live Music in the Orchard: C'ville Jazz Congregation

The C'ville Jazz Congregation is a collective of local musicians performing live in the orchard.

Live Music: Mike D'Antoni

Saturday Live Music with Scuffletown

Scuffletown is an acoustic high energy duo with Marc on guitar/vocals and John on harmonica, accordion, flute and vocals. Originals, roots, and high-energy music. Music 2-5 pm. No reservations, no cover charge.

Live Music: Patrick Dimeo

Live Music by Jeremy Huband, Jeff Petescia, and John Radomski 3-5pm

Join us at Blenheim Vineyards on Saturday, September 26 from 3–5 PM for an afternoon of free live music with Jeremy Huband, Jeff Petescia, and John Radomski. Settle in under the tent overlooking the vineyard, grab a glass or bottle of Blenheim wine, and spend an easy fall afternoon enjoying live music, good company, and vineyard views. Free admission | No reservations required.

Live Music: JJ Bevillaqua

Live music at Afton Mountain Vineyards with JJ Bevillaqua. Tasting Room open 11 AM - 7:30 PM.

Kat & The Travelers | Eastwood After Dark

Live music and dancing every Saturday night at The Barn. Featuring Kat & The Travelers.

Flamenco and Beyond with Beleza and Tracy Verkerke

A unique evening combining Beleza's Brazilian, Latin and Soul influenced repertoire with traditional Spanish Flamenco dance by Tracy Verkerke.

Live Music: David Wade and Black Mountain

Appalachian bluegrass from one of the area's most talented groups. Hitting all the bluegrass standards and favorites from Monroe to now.

Cherry Red: Rolling Stones Tribute

Cherry Red brings an incredible Rolling Stones tribute to Pro Re Nata Brewpub & Music Hall in Crozet, VA.

Wavelength Trio

Featuring Wavelength Trio — Andre LaVelle, Larry Bisgaier, Wave Milor. Bluesy jazzy vibrations plus original tunes.

Oktoberfest

Oktoberfest at Brewing Tree. Marzen and festbier on the taps, food from the Scratch Kitchen, and the beer garden set up for it. Family Field Day runs on the meadow the same afternoon, so bring the kids.

Oktoberfest | Every Weekend

Oktoberfest celebration running every weekend at Eastwood Farm and Winery.

Family Field Day

Sunday afternoon on the meadow for the whole crew. Yard games, the scavenger hunt, room to run, and a different featured game each week. Kanjam and Spike Ball are free to borrow at the River Bar.

Chiswell Book Club September Meeting

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

Live Music: Matt Burridge

Live Music: Alex Arbaugh

Guitarist and vocalist bringing original, guitar-driven rock and roll with a Southern-rock and Americana streak.

Music on the Deck: Michael Mulvaney

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

Meet the Artist: Frank Phillips, September 27th 2-4pm

Join us in the tasting room at Blenheim Vineyards and meet the artist, Frank Phillips, September 27th from 2-4pm. His artwork will be on display and available for purchase. We will have snacks and wine for sale by the glass, bottle, and flights.

BRIMS Ceol agus Céilí: Irish Session & Social Dance

The Céilí is back! Traditional Irish music session and social dance at Potter's Craft Cider.

Sunday Jazz and Blues featuring John D'earth

Sunday Jazz and Blues featuring John D'earth, 5:30-8:30 PM at Merrie Mill Farm & Vineyard.

Food Truck: PotLucky Cville at Starr Hill Crozet

At PotLucky, we specialize in crafting authentic, handmade Chinese steamed buns and dumplings, using traditional recipes with an added southern twist.

Trivia Night at Starr Hill Crozet

Join us every Tuesday for Trivia! Gather your best team of up to 6 and belly up for your chance to win!

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

Wine Down Wednesday with Cherry Red

Join us as Nick Pollack and his Rolling Stones cover band Cherry Red take the stage for a fantastic Wednesday evening at Keswick Vineyards.

Run, Walk, Crawl Club at WildManDan Brewery

Weekly community Run, Walk, Crawl Club meets every Wednesday at 6 PM at WildManDan Brewery in Afton. 21+ only establishment.

Vinyl Share at WildManDan Brewery

Weekly vinyl record share every Thursday 4-7 PM at WildManDan Brewery. Bring your records and enjoy craft beer. 21+ only.

Open Mic Night

Be the star! Share your music, comedy, vocal or poetry talents for 20 minutes & get a comp. glass of wine, beer or NA beer! Pre-register for your time slot. Sign-ups required.

Cider Bingo

Join us in the taproom for CIDER Bingo starting at 6PM!

Trail Run Club at Starr Hill Crozet

Join Cville Runners every Thursday at 6pm and take a jaunt on the Crozet Trails! Meet back at our tap room for pints!

Friday Sundowner's Music Series featuring Jacob Paul Allen

Enjoy the Friday Sundowner's music series from 5:30-8:30 PM at Merrie Mill Farm & Vineyard with Jacob Paul Allen.

Summer Sundown

Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 5:30–8 PM.

October Trivia with Tag Team Entertainment

Trivia night in the upstairs mezzanine with Tag Team Entertainment. Sip wine, test your knowledge, and win prizes.

Harvest Fest

Harvest Fest weekend at Cunningham Creek Winery & Brewery.

Pumpkin Decorating Workshop

Creative pumpkin decorating workshop at The Market at Grelen. Registration required.

Field Day with Small Town Rodeo at Blenheim Vineyards

Join us for Field Day at Blenheim Vineyards presented by WNRN radio, and enjoy an easygoing afternoon of live music, vineyard views, and time well spent together. Small Town Rodeo will be playing live from 3–5 PM under the tent overlooking the vineyard. Bring the whole family, invite your friends, and settle in for an afternoon of great wine, open skies, and community. Open until 7 PM. No tickets required, just show up and enjoy!

5th Biannual Art Festival & Book Fair pt. 2 at Merrie Mill

The 5th Biannual Art Festival & Book Fair returns for its second installment at Merrie Mill Farm & Vineyard. Saturday, October 3, 11:00 AM - 5:30 PM.

Beer & Grilled Cheese Pairing: Oktoberfest Bier

October featured pairing: Oktoberfest Bier paired with Local Monastery Gouda, sliced apples, and applebutter on Farmhouse Wheat Bread. Saturdays at 11:30 AM (before the taproom opens). Only 12 seats available — ticketed event, $24.79. Must purchase tickets in advance at SimpleTix.

Live Music | Matt Johnson

The Voice legend and local favorite Matt Johnson! Come grab a glass or bottle of your favorite Keswick wine and enjoy an afternoon of great music.

Oktoberfest

Oktoberfest at Brewing Tree. Marzen and festbier on the taps, food from the Scratch Kitchen, and the beer garden set up for it.

Live Music | Andy Tichenor

Collecting inspiration from many different sources, Andy pieces them together to create an eclectic mix of music.

Oktoberfest

Oktoberfest at Brewing Tree. Marzen and festbier on the taps, food from the Scratch Kitchen, and the beer garden set up for it. Family Field Day runs on the meadow the same afternoon, so bring the kids.

Live Music: Miles Pearce at Pippin Hill

Live music with Miles Pearce at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

Family Field Day

Sunday afternoon on the meadow for the whole crew. Yard games, the scavenger hunt, room to run, and a different featured game each week. Kanjam and Spike Ball are free to borrow at the River Bar.

Taste of Virginia: Wine & Food Grand Tasting

A grand tasting event featuring Virginia wines and food.

Sunday Jazz and Blues featuring Paulien

Sunday Jazz and Blues featuring Paulien, 1:00-4:00 PM at Merrie Mill Farm & Vineyard.

The Winemaker's Journey Part 1

In-depth wine tasting series with Associate Winemaker Gavin Baum in the Hillcrest Society Lounge. Features 8 wines in two themed flights, including vertical and horizontal tastings across vintages.

Paint + Sip "October Morning"

Autumn paint-and-sip class with Blue Ridge Brushes. No experience necessary, all materials included.

Music on the Deck: Paulo Franco

Join us for music on the deck from 2-5pm with Paulo Franco.

Food Truck: PotLucky Cville at Starr Hill Crozet

At PotLucky, we specialize in crafting authentic, handmade Chinese steamed buns and dumplings, using traditional recipes with an added southern twist.

Trivia Night at Starr Hill Crozet

Join us every Tuesday for Trivia! Gather your best team of up to 6 and belly up for your chance to win!

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

Wine Down Wednesday – Big Gavel Classic Band

Big Gavel Classic Band blends classic Americana acoustic with added percussion, creating a rhythmic and dynamic sound.

Trail Run Club at Starr Hill Crozet

Join Cville Runners every Thursday at 6pm and take a jaunt on the Crozet Trails! Meet back at our tap room for pints!

Virginia Wine Detour at Colony House Motor Lodge, Roanoke

A fall gathering for the thirsty & adventurous. In partnership with Lightwell Survey Wines, bloom Restaurant & Wine Bar and the Monticello Wine Trail. Friday-Sunday weekend with poolside cookout and wine tastings, Saturday reception, and four-course wine-pairing dinner on the lawn. Participating winemakers include Kirsty Harmon from Blenheim Vineyards, Emily Hodson from Veritas and Flying Fox Vineyard, Sebastian Zutant from Lightwell Survey and Damien Blanchon from Afton Mountain. Packages start at $785 (2 nights + 1 ticket). Colony House Motor Lodge, 3560 Franklin Road SW, Roanoke, VA.

Friday Sundowner's Music Series featuring Sharif

Enjoy the Friday Sundowner's music series from 5:30-8:30 PM at Merrie Mill Farm & Vineyard with Sharif.

Music Bingo

Music Bingo night! 6:30 to 8:30 pm. Reservations recommended. Wine, beer, mocktail, pizza available.

Kubota Tour – Fall Color Around The Nursery

Guided Kubota tour exploring fall color around the nursery at The Market at Grelen. Registration required.

Live Music | Josh Davidson

Josh Davidson hails from the Blue Ridge Mountains of Virginia and plays a wide variety of music.

Live Music at Blenheim: Cry Babies 3-5pm

Join us at Blenheim Vineyards on Saturday, October 10 from 3–5 PM for an afternoon of free live music with Cry Babies. Settle in under the tent overlooking the vineyard, grab a glass or bottle of Blenheim wine, and enjoy a fall afternoon of live music, good company, and vineyard views. Free admission | No reservations required.

Crown Club Saturday: Chocolate and Wine Pairing with Gearharts Fine Chocolates

Crown Club members and their guests will be guided through sweet chocolate and wine pairings by Gearharts Fine Chocolates. Advance registration is requested.

Live Music – Henley & Lou

Experience music that lifts your spirits, fills your heart, and gets your feet moving. Henley & Lou bring an unforgettable performance to Keswick Vineyards.

Fall Oyster Roast with Salty Bottom Blue Oysters

Join us Sunday October 11th for a perfect fall afternoon at the vineyard! Fresh oysters from Salty Bottom Blue paired with Keswick wines.

Family Field Day

Sunday afternoon on the meadow for the whole crew. Yard games, the scavenger hunt, room to run, and a different featured game each week. Kanjam and Spike Ball are free to borrow at the River Bar.

Music on the Deck: Charlie & Ian

Join us for music on the deck from 2-5pm with Charlie & Ian.

Harvest Wine Dinner

Harvest Wine Dinner with Chef Andy.

Food Truck: PotLucky Cville at Starr Hill Crozet

At PotLucky, we specialize in crafting authentic, handmade Chinese steamed buns and dumplings, using traditional recipes with an added southern twist.

Trivia Night at Starr Hill Crozet

Join us every Tuesday for Trivia! Gather your best team of up to 6 and belly up for your chance to win!

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

Trail Run Club at Starr Hill Crozet

Join Cville Runners every Thursday at 6pm and take a jaunt on the Crozet Trails! Meet back at our tap room for pints!

Team Trivia

6:30-8 pm. Reservations recommended.

Friday Sundowner's Music Series featuring Bailey Hayes

Enjoy the Friday Sundowner's music series from 5:00-9:00 PM at Merrie Mill Farm & Vineyard with Bailey Hayes.

Lecture: Fall Color at Grelen

Free lecture on fall color at Grelen nursery. Registration required.

Pumpkin Decorating Workshop

Creative pumpkin decorating workshop at The Market at Grelen. Registration required.

Simply Trending Catering BBQ

BBQ food truck pop-up at Cunningham Creek Winery & Brewery.

Harvest Party

An intimate, behind-the-scenes harvest celebration in the production facility. Wander the tank room, barrel room, and crush pad with tastings straight from barrels. Enjoy a welcome glass, Italian-inspired menu from Luce Pasta, and live music. Meet Winemaker Matthieu Finot, Associate Winemaker Connor Jooste, and Wine Director Karine Malifarge. Limited tickets. Wine Club members save $10.

Family Field Day

Sunday afternoon on the meadow for the whole crew. Yard games, the scavenger hunt, room to run, and a different featured game each week. Kanjam and Spike Ball are free to borrow at the River Bar.

Live Music: Gina Sobel at Pippin Hill

Live music with Gina Sobel at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

Sunday Jazz and Blues featuring Whiskey Django

Sunday Jazz and Blues featuring Whiskey Django, 1:00-4:00 PM at Merrie Mill Farm & Vineyard.

Music on the Deck: Michael Mulvaney

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

Food Truck: PotLucky Cville at Starr Hill Crozet

At PotLucky, we specialize in crafting authentic, handmade Chinese steamed buns and dumplings, using traditional recipes with an added southern twist.

Trivia Night at Starr Hill Crozet

Join us every Tuesday for Trivia! Gather your best team of up to 6 and belly up for your chance to win!

Live Music: Andrew Beverly at Pippin Hill

Live music with Andrew Beverly at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

October Bachata with C'Ville Bachata Social

Bachata and salsa dancing with C'Ville Bachata Social. Lessons 5–6 PM, then open dancing with drinks, food, and sunset views. All levels welcome.

Friday Sundowner's Music Series featuring Mercy Creek

Enjoy the Friday Sundowner's music series from 5:30-8:30 PM at Merrie Mill Farm & Vineyard with Mercy Creek.

Music Bingo

Music Bingo night! 6:30 to 8:30 pm. Reservations recommended. Wine, beer, mocktail, pizza available.

The Winemaker's Journey Part 2

Second session of the in-depth winemaker tasting series with Associate Winemaker Gavin Baum. Completely different wines from Part 1.

Paint + Sip "Stack o' Pumpkins"

Autumn-themed paint-and-sip class with Blue Ridge Brushes. No experience necessary, all materials included.

Pumpkin Decorating Workshop

Creative pumpkin decorating workshop at The Market at Grelen. Registration required.

Chen's Kitchen

Chinese dumplings & fried rice from Chen's Kitchen.

Planning and Planting the Home Orchard Workshop

Thinking about starting your own home orchard? Learn about planning and planting in this all-day workshop.

Fall Festival

Details coming soon.

Live Music at Blenheim: FOG 3-5pm

Join us at Blenheim Vineyards on Saturday, October 24 from 3–5 PM for an afternoon of free live music with FOG. Settle in under the tent overlooking the vineyard, grab a glass or bottle of Blenheim wine, and enjoy a fall afternoon of live music, good company, and vineyard views. Free admission | No reservations required.

Heart of Virginia Artisans Autumn Market

Autumn-themed market featuring local makers, curated gifts, handcrafted goods, adult beverages, and bites.

Family Field Day

Sunday afternoon on the meadow for the whole crew. Yard games, the scavenger hunt, room to run, and a different featured game each week. Kanjam and Spike Ball are free to borrow at the River Bar.

Witches' Day Out

Gather your coven for a witch-themed Halloween celebration and costume contest supporting Crozet Cares Closet.

Sunday Jazz and Blues featuring John D'earth (last of the season!)

The final Sunday Jazz and Blues of the season features John D'earth. 1:00-4:00 PM at Merrie Mill Farm & Vineyard.

Meet the Artist: Allie Kelly, October 25th 2-4pm

Join us in the tasting room at Blenheim Vineyards and meet the artist, Allie Kelly, October 25th from 2-4pm. Her artwork will be on display and available for purchase. We will have snacks and wine for sale by the glass, bottle, and flights. Allie Kelly is an artist living in Buckingham County, Virginia, painting from nature in oil, watercolor, and natural pigment.

Early Mountain X Barboursville Vineyards Collaborative Wine Dinner

A collaborative wine dinner featuring Early Mountain and Barboursville Vineyards.

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

Friday Sundowner's Music Series featuring Wavelength (last of the season!)

The final Friday Sundowner's music series of the season from 5:30-8:30 PM at Merrie Mill Farm & Vineyard with Wavelength.

Big City Band

Live music at Pro Re Nata Brewpub & Music Hall featuring Big City Band.

Kubota Tour – Fall Color Around The Nursery

Guided Kubota tour exploring fall color around the nursery at The Market at Grelen. Registration required.

Halloween at Brewing Tree

Trunk or Treat, a costume contest, the scavenger hunt, and Fireside Tales from the Crypt after dark. Full lineup and times to come.

NOCTURNE II Halloween Ball at Merrie Mill

The second annual NOCTURNE Halloween Ball at Merrie Mill Farm & Vineyard. Saturday, October 31, 5:00-11:00 PM. Ticketed event via Humanitix. Costumes encouraged.

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

Open Mic Night

Be the star! Share your music, comedy, vocal or poetry talents for 20 minutes & get a comp. glass of wine, beer or NA beer! Pre-register for your time slot. Sign-ups required.

Outdoor Movie Night: Kelly's Heroes

Outdoor movie screening of the classic 1970 war comedy Kelly's Heroes. Evening under the stars at Horton Vineyards.

November Trivia with Tag Team Entertainment

Trivia night in the upstairs mezzanine with Tag Team Entertainment. Sip wine, test your knowledge, and win prizes.

Live Music: Mercy Creek at Pippin Hill

Live music with Mercy Creek at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

Music Bingo

Music Bingo night! 6:30 to 8:30 pm. Reservations recommended. Wine, beer, mocktail, pizza available.

Lucy's Snack Shack

Smashburgers, veggie burgers, fries, shakes and more from Lucy's Snack Shack.

Crown Club Saturday: Murder Mystery Party

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

Silver Starlight Opportunity Ball

Come enjoy a memorable night for a great cause at Afton Mountain Vineyards. Saturday, November 14, 2026.

NCCF Silver Starlight Opportunity Ball at Veritas

A magical evening celebrating the 25th anniversary of Nelson County Community Fund (NCCF) at Veritas Vineyards. Enjoy music, dancing, and a three-course dinner paired with fine wine. Features a live auction with Ken Farmer from PBS's Antiques Roadshow and a silent auction. Event runs 6:30 PM - 11:45 PM. Cocktail and formal attire welcome; silver sparkles encouraged! $250+ per person. Raises critical funds for food access, housing, education, youth development, and health initiatives across Nelson County.

Live Music: Willie De at Pippin Hill

Live music with Willie De at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

Team Trivia

6:30-8 pm. Reservations recommended.

Simply Trending Catering BBQ

BBQ food truck pop-up at Cunningham Creek Winery & Brewery.

Brims & Vino Hat Workshop

Fall hat design workshop with For the Love of Hats! Guests design a one-of-a-kind hat while sipping Hazy Mountain beverages. Advance tickets required.

Heart of Virginia Artisans Giving Thanks Market

Thanksgiving-themed market with local artisans, handcrafted autumn goods, warm bites, and adult beverages.

Live Music: Vincent Zorn at Pippin Hill

Live music with Vincent Zorn at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

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!

Wine Wednesday

Tasting room open until 8:30pm! Food trucks serving 4:00-7:30pm, trivia in the pavilion starting at 6:00pm with gift cards up for grabs.

Black Friday Music featuring Wavelength

Celebrate Black Friday with live music from Wavelength at Merrie Mill Farm & Vineyard. Friday, November 27, 1:00-4:00 PM.

November Bachata with C'Ville Bachata Social

Bachata and salsa dancing with C'Ville Bachata Social. Lessons 5–6 PM, then open dancing. All levels welcome.

Meet the Artists: Virginia Rieley & Eliza Evans, November 29th 2-4pm

Join us in the tasting room at Blenheim Vineyards and meet the artists, Virginia Rieley & Eliza Evans. 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 paints acrylic portraits from life; Virginia Rieley creates mixed media collage combining photography with watercolor and pen. Together they co-create the Every Day is a Holiday Calendar, self-published annually since 2006.

December Trivia with Tag Team Entertainment

Trivia night in the upstairs mezzanine with Tag Team Entertainment. Sip wine, test your knowledge, and win prizes.

Annual Holiday Market at Merrie Mill

Merrie Mill Farm & Vineyard's Annual Holiday Market. Saturday, December 5, 11:30 AM - 5:00 PM. Shop local vendors and enjoy the festive atmosphere.

December Bachata with C'Ville Bachata Social

Bachata and salsa dancing with C'Ville Bachata Social. Lessons 5–6 PM, then open dancing. All levels welcome.

Live Music: Max Mandu at Pippin Hill

Live music with Max Mandu at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

Crown Club Saturday: Gift Exchange

Members of the wine club and their guests will be exchanging gifts during a special holiday celebration.

Live Music: Kim & Jimbo at Pippin Hill

Live music with Kim & Jimbo at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

Holiday Open House

Join Chiswell Farm & Winery for live music, Christmas cookies, and traditional mulled wine at the holiday open house.

Live Music: Sue Harlow at Pippin Hill

Live music with Sue Harlow at Pippin Hill Farm & Vineyard, 12pm-3pm. Enjoy live tunes, great food and wine.

New Year's Eve Black & White Ball at Veritas

Ring in 2027 at Veritas with an elegant Black & White Ball. Enjoy a wine hour with passed hors d'oeuvres followed by a five-course dinner paired with Veritas wines. DJ Derek Tobler keeps the dance floor moving through midnight, and guests receive a special late-night snack to take home. Dress in your finest black, white, or combination. 7:00 PM - 12:30 AM. $250 per person (Wine Club Members receive $50 off first two tickets).