Events in Charlottesville Wine Country

Food Truck: PotLucky Cville

Trivia Night

Max Mandu Live

Live music at Pippin Hill Farm & Vineyard featuring Max Mandu.

Wine Wednesday at King Family Vineyards

Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm! 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.

Open Artist Night

Wine Down Wednesday with The Unsuitables

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

The Front Porch Presents: Jake Blount Band

The Front Porch concert series at Potter's Craft Cider presents Jake Blount Band. Grab your tickets! 5:30pm.

Run, Walk, Crawl Club

Weekly Wednesday Run, Walk, Crawl Club. Meet at WildManDan Brewery.

Locals Vinyl Share Night

Weekly Thursday Locals Vinyl Share night with $5 pints.

Porch Nights: Jim Richardson

Game Night!

Play one of our games or bring your own! $15 pitchers from 5-9pm.

Trail Run Club

Team Trivia Night

Team Trivia Night at Cunningham Creek Winery. 6:30–8pm. Reservations recommended.

The Front Porch Presents: Songwriter's Open Mic

Calling all songwriters! The Front Porch Open Mic series at Potter's Craft Cider welcomes original voices. 7pm.

Live Music: Bluzonia

A four-piece band featuring the drummer from the Jon Spear Band. Free live music in the beer garden at Brewing Tree.

Friday Night Out: Bomar & Ritter at DuCard

Friday Night Out with music by Bomar & Ritter and 1/2 price wine flights at DuCard Vineyards. 5pm-8pm.

Friday Sundowner's Music Series featuring Mercy Creek

Tara Mills Band Live

A blend of folk, bluegrass, and Americana at Potter's Craft Cider. 5:30pm.

Boozy Trivia Night!

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

Ken Farmer & The Authenticators

A priceless night of rocking good fun featuring KEN FARMER & THE AUTHENTICATORS! Friday, September 18th, from 6 to 8:30pm. Open to all. No cover.

Paint & Sip: Dark Sunset

Come paint with us at Potter's Craft Cider! A guided Paint & Sip painting event. 6pm.

Sunset Soirée: Chickenhead Blues with Sweet Jane's Kitchen

Music Bingo

Get ready for another brand-new kind of Friday night fun at Grace Estate! Our first few Music Bingo Nights were a huge success and an absolute blast — so we're bringing it back with our friends at Tag Team Entertainment.

Music Bingo Night

Music Bingo hosted by Tag Team Entertainment. Blend of music, games, and wine set against a gorgeous sunset.

The Art of The Low Maintenance Garden

Free Saturday workshop at The Market at Grelen covering low maintenance garden design and building a winter interest garden.

Harvest Fest at Southwest Mountains Vineyards

Second Annual Harvest Fest at Southwest Mountains Vineyards! Celebrate the beauty of harvest time in the Monticello AVA. Gather your friends for an unforgettable day at the vineyard. 11am-5:30pm.

Grilled Cheese & Beer Pairing

Saturday grilled cheese and beer pairing with limited seating.

Bouquet Making Workshop with Blooms4Good

Floral bouquet workshop using locally sourced vases and Blooms4Good's locally grown flowers. Proceeds from this workshop support local charities.

Live Music – Rixeyville Revival

Come out and rock with the Rixeyville Revival Band — bringing the best hits from the classic rock era.

Oktoberfest with Guten Morgen Band

Celebrate Oktoberfest at Cunningham Creek Winery! Enjoy the Guten Morgen Band from Staunton playing German, Austrian, and Central European waltzes and polkas. Dance and sing along! German foods from Chef Roderick and lots of beer.

Horton on the Go: Stratford Hall Wine & Oyster Festival

Horton Vineyards exhibiting at the Stratford Hall Wine & Oyster Festival.

Harvest Fest Grape Stomp!

Grab a slot and come have a blast! The grape stomp is the highlight of our Harvest Fest — a little messy, a lot of fun, and a great way to get in the spirit of the season. Part of Harvest Fest (11am-5:30pm). 1pm-4pm.

Music in the Mountains: Kat and the Travelers

Music in the Mountains with Kat and the Travelers at DuCard Vineyards. 2pm-5pm.

Live Music: Andrew Beverly

Free live music in the beer garden at Brewing Tree Beer Company, Afton VA.

Live Music with Tucker Wyatt

Free live music under the tent overlooking the vineyard.

Catching Fish & Chips & Mercy Creek Music

Catching Fish & Chips & Mercy Creek Music

Midnight Buzz at Glass House

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

The Wavelength | Eastwood After Dark

The Cows Live

Rock as reggae, reggae as ska and ska as rock after too much Grateful Dead. The Cows play Potter's Craft Cider. 5:30pm.

The Rivanna Band

Hailing from right here in Virginia, the Rivanna Band brings a mixture of rock, country, and indie music carefully curated from hits and originals. 6–9pm.

Saturday Night Special: The Inclinators with Crozet Seafood Supply

Back to Cool Improv Night

Hot on the heels of our 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

A high-energy Def Leppard tribute show at Pro Re Nata Brewpub & Music Hall in Crozet. 111+ interested. 7pm.

Live Music with Rachael Karpo

Rachael is a New Jersey native and Air Force veteran — a soloist who pours passion into every performance.

Paint & Sip: Hydrangea Wine Glass

Matty Metcalfe Live

Live music at Pippin Hill Farm & Vineyard featuring Matty Metcalfe.

Sunday Blues and Jazz featuring Wavelength

Sunday Session: The Trio

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

Virginia Singer-Songwriters performing original acoustic songs at Potter's Craft Cider. 2pm.

Live Music: Starfire

Free live music in the beer garden at Brewing Tree Beer Company, Afton VA.

Willie DE at Glass House

Sunday Fun Day with Willie DE treating guests to his awesome bluesy rock sounds. Sunday, September 20th, from 2 to 5pm. Open to all. No cover.

Live Music with Rick Martin

Music on the Deck with Rick Martin

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

Music in the Mountains: Pat Anderson at DuCard

Music in the Mountains with Pat Anderson at DuCard Vineyards. 2pm-5pm.

Food Truck: PotLucky Cville

Trivia Night

Wine Wednesday at King Family Vineyards

Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm! 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.

Wine Down Wednesday – South Canal Street Band

South Canal Street brings the best of classic soul, R&B, and rock for a lively Wednesday evening at Keswick.

Run, Walk, Crawl Club

Weekly Wednesday Run, Walk, Crawl Club. Meet at WildManDan Brewery.

Locals Vinyl Share Night

Weekly Thursday Locals Vinyl Share night with $5 pints.

Porch Nights: Solo Steve

The Front Porch Presents: Darrell Scott Live

The Front Porch concert series at Potter's Craft Cider presents Darrell Scott. Grab your tickets! 5:30pm.

Bold Book Club: Like a Moth to a Flame

Bold Book Club is back! This month we're diving into Like a Moth to a Flame by Lillith Abendroth. Join us September 24th at 6PM for good books, good conversation, and (of course) good cider. Bring your copy of the book and your first cider is FREE!

Live Music: Bryan Horowitz

Free live music in the beer garden at Brewing Tree Beer Company, Afton VA.

Friday Night Out: Acoustic Aubrey at DuCard

Friday Night Out with Acoustic Aubrey and half price wine flights at DuCard Vineyards. 5pm-8pm.

Friday Sundowner's Music Series featuring Johnathan Paige Brown

Villains Trivia Night

Gather your crew and join us for a night dedicated to all things Villains! Trivia starts at 6:00 PM at Bold Rock Nellysford. Grab a cider, bring your smartest (or most evil) teammates, and compete for prizes and bragging rights.

Lockjaw Classic Rock Band at Glass House

Lockjaw Classic Rock Band returns to the tropical oasis covering fan favorites from the 60s through the 80s and beyond. Friday, September 25th.

Friday Night Soirée: Ken Farmer & the Authenticators with Crozet Seafood Supply

Paint + Sip: Field of Fireflies

Paint with Blue Ridge Brushes at Hazy Mountain Vineyards. No experience necessary, all materials included. Taught by a professional artist guiding you through various techniques.

Veritas Supper Series & Harvest Dinner

The Supper Series concludes with a summer truffle supper rooted in Italian cuisine. Enjoy an elegant, coursed dinner celebrating one of the world's most prized ingredients, thoughtfully paired with Veritas wines. $150 per person including wine pairings. Wine Club Members receive 20% off first two tickets.

Dinner & a Movie Night at SMV

Southwest Mountain's Dinner & A Movie Series is BACK. New nights this September & October. Reservations required. 6:30pm-10:30pm.

Pumpkin Decorating Workshop

A fun seasonal workshop at The Market at Grelen. Decorate pumpkins amid the beautiful nursery and display gardens.

Cheese & Wine Pairing featuring Truckle Cheesemongers

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 Michael Shaps wines. $70 per person | $60 Wine Club Members. Space is limited — advance reservations required.

Grilled Cheese & Beer Pairing

Saturday grilled cheese and beer pairing with limited seating.

Fall Seafood Saturday at DuCard

Fall Seafood Saturday returns! Nomini Bay Oyster Ranch brings the freshest oysters from the Northern Neck: raw, steamed, grilled, and grilled with toppings, plus steamed shrimp. Live music by South Canal Street. $12 in advance, $20 at gate. Ticket includes souvenir logo wine glass. 12pm-6pm.

Horton on the Go: Smith Mountain Lake Wine Festival

Horton Vineyards exhibiting at the Smith Mountain Lake Wine Festival.

Live Music: Patrick Dimeo

Free live music in the beer garden at Brewing Tree Beer Company, Afton VA.

Live Music with Jeremy Huband

Free live music under the tent overlooking the vineyard.

Live Music: JJ Bevillaqua

Live Music: JJ Bevillaqua

Robert Jospé Trio at Glass House

The Robert Jospé Trio returns to Glass House for an evening filled with high energy, world class jazz!

Scuffletown Live

Scuffletown is an acoustic high-energy duo with Marc on guitar/vocals and John on harmonica, accordion, flute, and vocals. A unique blend of originals and roots music.

Kat & The Travelers | Eastwood After Dark

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. 5:30pm.

David Wade and Black Mountain

It's Appalachia. It's fall. One of the area's most talented bluegrass groups hits all the bluegrass standards and favorites from Monroe to now. 6–9pm.

Line Dancing Country Night with Dancin' Cat

Grab your cowboy boots for a fun-filled night of Line Dancing with Dancin' Cat. Whether you're a pro or a newbie, enjoy great music, good vibes, and fantastic wine.

Cherry Red: Rolling Stones Tribute

Cherry Red brings a Rolling Stones tribute show to Pro Re Nata Brewpub & Music Hall in Crozet. 7pm.

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! 1pm-3pm.

Sunday Session: The Michael Elswick Gathering

Meet the Artist: Frank Phillips

Meet artist Frank Phillips in the tasting room. Artwork on display and available for purchase. Snacks and wine available.

Music in the Mountains with Ben Mason

Join us in the foothills for an afternoon of wine, entertainment, and relaxation. Ben Mason is a local singer-songwriter with an expansive repertoire of originals and covers alike. No cover. 2pm-5pm.

Live Music: Alex Arbaugh

Original guitar-driven rock and roll with a Southern-rock and Americana streak. Alex fronts Virginia band Sun-Dried Opossum. Free music in the beer garden.

Wavelength Trio at Glass House

Wavelength Trio performance — Andre LaVelle, Larry Bisgaier, Wave Milor. Bluesy jazzy vibrations plus original tunes. Bring a picnic and well-behaved canines welcome.

BRIMS Ceol agus Céilí: Irish Session & Social Dance

The Céilí is back at Potter's Craft Cider! Traditional Irish session music and social dancing. 3pm.

Sunday Jazz and Blues featuring John D'earth

Food Truck: PotLucky Cville

Trivia Night

Wine Wednesday at King Family Vineyards

Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm! 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.

Wine Down Wednesday with Cherry Red

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

Porch Nights: Solo Steve

September Quarterly Wine Club Installment Party

Open Mic Night

Be the star at Cunningham Creek Winery! Share your music, comedy, vocal or poetry talents for 20 minutes and get a complimentary glass of wine, beer, or NA beer. Pre-register for your time slot.

Cider Bingo

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

Friday Night Out: John Kelly at DuCard

Smooth music from John Kelly, a long-time local musician, writer, and producer. Rock-solid guitar playing and singing rooted in traditional and country styles. Half price wine flights after 4pm. No cover. 5pm-8pm.

Friday Sunset Soirée: Scuffletown with Two Brothers Southwestern Grill

Summer Sundown at Chiswell

Local musicians and food trucks help savor the Friday evening sunset. Monthly series from May through October. 6pm-8:30pm.

Harvest Fest

Annual Harvest Festival at Cunningham Creek Winery. A seasonal celebration of the harvest.

Pumpkin Decorating Workshop

A fun seasonal workshop at The Market at Grelen. Decorate pumpkins amid the beautiful nursery and display gardens.

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 the music.

Music in the Mountains with Mo & Mary Mac

"Wine Down" with local musicians Mo & Mary Mac. These talented singer-songwriters may even play the original song they wrote for DuCard. No cover. 2pm-5pm.

Horton on the Go: 23rd Annual Festival of the Grape

Horton Vineyards exhibiting at the 23rd Annual Festival of the Grape.

Field Day with Small Town Rodeo (presented by WNRN)

Field Day presented by WNRN radio. Small Town Rodeo live under the tent. Family friendly.

The Unsuitables | Eastwood After Dark

Live Music | Andy Tichenor

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

Miles Pearce Live

Live music at Pippin Hill Farm & Vineyard featuring Miles Pearce.

Taste of Virginia: Wine & Food Grand Tasting

Taste of Virginia Wine & Food Grand Tasting at Early Mountain Vineyards. 1:00PM-4:00PM. Reservations required.

Sunday Session: Olivarez Trio

Wine Wednesday at King Family Vineyards

Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm! 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.

Porch Nights: Sharif

Horton on the Go: Mount Vernon Fall Wine Festival

Horton Vineyards exhibiting at the Mount Vernon Fall Wine Festival.

Sunset Soirée: Don't Look Up Band with Two Brothers Southwestern Grill

Music Bingo

Music Bingo at Cunningham Creek Winery. Test your musical knowledge! 6:30–8:30pm. Reservations recommended. Wine, beer, mocktail, and pizza available.

Kubota Tour – Fall Color Around The Nursery

A guided Kubota tour of the 1,000-acre tree nursery at The Market at Grelen, showcasing spectacular fall foliage colors.

Live Music with Cry Babies

Free live music under the tent overlooking the vineyard.

Jason Burke: Bunch O'Mugs | Eastwood After Dark

Saturday Night Special: Dave's Basement

Crown Club Saturday: Chocolate & Wine Pairing with Gearharts

Crown Club members and guests will be guided through sweet pairings by Gearharts Fine Chocolates. Advance registration requested. 6pm-8pm.

Sunday Soirée: Robert Jospé Trio

Harvest Wine Dinner with Chef Andy

A special Harvest Wine Dinner at Cunningham Creek Winery prepared by Chef Andy.

Wine Wednesday at King Family Vineyards

Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm! 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.

Porch Nights: Michael Clem

Team Trivia Night

Team Trivia Night at Cunningham Creek Winery. 6:30–8pm. Reservations recommended.

Sunset Soirée: Chickenhead Blues with Twisted Provisions

Pumpkin Decorating Workshop

A fun seasonal workshop at The Market at Grelen. Decorate pumpkins amid the beautiful nursery and display gardens.

Horton on the Go: Town Point Virginia Fall Wine Festival

Horton Vineyards exhibiting at the Town Point Virginia Fall Wine Festival.

Lecture: Fall Color at Grelen

Free Saturday lecture at The Market at Grelen on enjoying fall color in your garden.

The Wavelength | Eastwood After Dark

Gina Sobel Live

Live music at Pippin Hill Farm & Vineyard featuring Gina Sobel.

Sunday Session: The Trio

Andrew Beverly Live

Live music at Pippin Hill Farm & Vineyard featuring Andrew Beverly.

Wine Wednesday at King Family Vineyards

Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm! 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.

Porch Nights: Ty Burkhardt

Music Bingo

Music Bingo at Cunningham Creek Winery. Test your musical knowledge! 6:30–8:30pm. Reservations recommended. Wine, beer, mocktail, and pizza available.

Planning and Planting the Home Orchard

Thinking about starting your own home orchard? Learn from the experts at Albemarle Ciderworks.

Pumpkin Decorating Workshop

A fun seasonal workshop at The Market at Grelen. Decorate pumpkins amid the beautiful nursery and display gardens.

Fall Festival at Brewing Tree

Annual Fall Festival at Brewing Tree Beer Company in the beer garden. Details coming soon.

Live Music with FOG

Free live music under the tent overlooking the vineyard.

Wine & Design at Horton Vineyards

Wine & Design at Horton Vineyards in Collaboration with Monica Garrett Interiors.

Classic Road | Eastwood After Dark

Witches' Day Out at Chiswell

Gather your coven for a witch-themed Halloween celebration and costume contest, supporting Crozet Cares Closet. Sunday, Oct 25. 1pm-4pm.

Meet the Artist: Allie Kelly

Meet artist Allie Kelly in the tasting room. Artwork on display and available for purchase.

Early Mountain X Barboursville Vineyards Dinner

Collaborative wine dinner with Early Mountain and Barboursville Vineyards. 6:00 PM. Reservations required.

Wine Wednesday at King Family Vineyards

Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm! 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.

Big City Band

Live music at Pro Re Nata Brewpub & Music Hall in Crozet. Mountain views, craft beer, and great live entertainment. 7pm.

Kubota Tour – Fall Color Around The Nursery

A guided Kubota tour of the 1,000-acre tree nursery at The Market at Grelen, showcasing spectacular fall foliage colors.

Open Mic Night

Be the star at Cunningham Creek Winery! Share your music, comedy, vocal or poetry talents for 20 minutes and get a complimentary glass of wine, beer, or NA beer. Pre-register for your time slot.

Salute & Sip: A Military K9 Tribute

Salute & Sip: A Military K9 Tribute event at Horton Vineyards.

Mercy Creek Live

Live music at Pippin Hill Farm & Vineyard featuring Mercy Creek.

Music Bingo

Music Bingo at Cunningham Creek Winery. Test your musical knowledge! 6:30–8:30pm. Reservations recommended. Wine, beer, mocktail, and pizza available.

Crown Club Saturday: Murder Mystery Party

Crown Club members and guests are invited to solve Chiswell's murder mystery. Saturday, November 14. 5:30pm-7:30pm.

NCCF Silver Starlight Opportunity Ball at Veritas

Celebrate the 25th anniversary of Nelson County Community Fund with a festive evening of music, dancing, and a three-course dinner paired with Veritas wines. Live auction hosted by Ken Farmer from PBS's Antiques Roadshow. 6:30pm–11:45pm. Cocktail or formal attire; silver sparkles encouraged! $250+

Willie De Live

Live music at Pippin Hill Farm & Vineyard featuring Willie De.

Team Trivia Night

Team Trivia Night at Cunningham Creek Winery. 6:30–8pm. Reservations recommended.

Vincent Zorn Live

Live music at Pippin Hill Farm & Vineyard featuring Vincent Zorn.

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! 1pm-3pm.

Music Bingo

Music Bingo at Cunningham Creek Winery. Test your musical knowledge! 6:30–8:30pm. Reservations recommended. Wine, beer, mocktail, and pizza available.

Meet the Artists: Virginia Rieley & Eliza Evans

Meet artists Virginia Rieley & Eliza Evans. Artwork on display and available for purchase.

Port Tasting at Horton Vineyards

Port Tasting event at Horton Vineyards.

Max Mandu Live

Live music at Pippin Hill Farm & Vineyard featuring Max Mandu.

Music Bingo

Music Bingo at Cunningham Creek Winery. Test your musical knowledge! 6:30–8:30pm. Reservations recommended. Wine, beer, mocktail, and pizza available.

Crown Club Saturday: Holiday Gift Exchange

Wine club members and their guests will exchange gifts during a special holiday celebration. Saturday, December 12. 5:30pm-7:30pm.

Kim & Jimbo Live

Live music at Pippin Hill Farm & Vineyard featuring Kim & Jimbo.

Team Trivia Night

Team Trivia Night at Cunningham Creek Winery. 6:30–8pm. Reservations recommended.

Holiday Open House at Chiswell

Live music, Christmas cookies, and traditional mulled wine at Chiswell's holiday open house. Friday, December 18. 5:30pm-7:30pm.

Sue Harlow Live

Live music at Pippin Hill Farm & Vineyard featuring Sue Harlow.

New Year's Eve Black & White Ball at Veritas

Welcome 2027 with an elegant evening of exceptional food, Virginia wine, and dancing. Wine hour and passed hors d’oeuvres, then an indulgent five-course dinner paired with Veritas wines, followed by dancing with DJ Derek Tobler through midnight. Dress in black, white, or a combination. $250 per person. Wine Club Members receive $50 off each of the first two tickets.