Charlottesville Wine Country
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Live music, tastings, festivals and more across 60+ wineries, cideries and breweries.
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Music
Friday Sundowner's Music Series featuring Jacob Paul Allen
Fri, Oct 2, 2026
5:30 PM – 8:30 PM
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Festival
Harvest Fest
Sat, Oct 3, 2026
11:00 AM
Annual Harvest Festival at Cunningham Creek Winery - Day 1
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Music
Field Day: Small Town Rodeo Live Music
Sat, Oct 3, 2026
3:00 PM – 5:00 PM
Join Blenheim Vineyards for Field Day! Enjoy live music from Small Town Rodeo from 3-5pm while sipping estate wines. Free event, no ticket required. Luce Italian food truck on-site.
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Festival
Harvest Fest
Sun, Oct 4, 2026
11:00 AM
Annual Harvest Festival at Cunningham Creek Winery - Day 2
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Music
Music on the Deck
Sun, Oct 4, 2026
2:00 PM – 5:00 PM
Enjoy live music with Paulo Franco on the deck at Cardinal Point Winery. Relax with a glass of wine and beautiful views.
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Tasting
Wine Wednesday
Wed, Oct 7, 2026
4:30 PM – 8:30 PM
Join King Family Vineyards every Wednesday for Wine Wednesday! The tasting room stays open until 8:30pm and food trucks are on-site from 4:30-7:30pm. Perfect evening to relax with a great glass of wine.
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Trivia
'Wine Down' Trivia Night
Fri, Oct 9, 2026
6:00 PM – 8:00 PM
Ready to put your knowledge to the test? Wine Down Trivia Night is a fan favorite at Grace Estate — hosted by Tag Team Entertainment, bringing big laughs, friendly competition, and lots of wine under a stunning sunset. Come sip, play, and unwind!
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Music
Cry Babies Live Music
Sat, Oct 10, 2026
3:00 PM – 5:00 PM
Come out to Blenheim Vineyards and enjoy live music from the Cry Babies from 3-5pm. Free event, no ticket required.
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Tasting
Chocolate and Wine Pairing with Gearharts Fine Chocolates
Sat, Oct 10, 2026
6:00 PM – 8:00 PM
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Special Event
Fall Oyster Roast with Salty Bottom Blue Oysters
Sun, Oct 11, 2026
12:00 PM – 5:00 PM
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Music on the Deck
Sun, Oct 11, 2026
2:00 PM – 5:00 PM
Enjoy live music on the deck at Cardinal Point Winery. Relax with a glass of wine and beautiful views.
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Tasting
Wine Wednesday
Wed, Oct 14, 2026
4:30 PM – 8:30 PM
Join King Family Vineyards every Wednesday for Wine Wednesday! The tasting room stays open until 8:30pm and food trucks are on-site from 4:30-7:30pm. Perfect evening to relax with a great glass of wine.
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Music
Friday Sundowner's Music Series featuring Bailey Hayes
Fri, Oct 16, 2026
5:00 PM – 9:00 PM
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Music
Music Bingo
Fri, Oct 16, 2026
6:00 PM – 8:00 PM
Get ready for Friday night fun at Grace Estate! Music Bingo Night hosted by Tag Team Entertainment — 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!
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Special Event
Harvest Party
Sat, Oct 17, 2026
6:00 PM – 9:00 PM
Celebrate the harvest season at King Family Vineyards! Enjoy a festive evening with wine, food, and fall fun. Ticketed event — reserve your spot in advance.
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Music
Music on the Deck — Mulvaney Music
Sun, Oct 18, 2026
2:00 PM – 5:00 PM
Enjoy live music with Mulvaney Music on the deck at Cardinal Point Winery. Relax with a glass of wine and beautiful views.
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Tasting
Wine Wednesday
Wed, Oct 21, 2026
4:30 PM – 8:30 PM
Join King Family Vineyards every Wednesday for Wine Wednesday! The tasting room stays open until 8:30pm and food trucks are on-site from 4:30-7:30pm. Perfect evening to relax with a great glass of wine.
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Music
Friday Sundowner's Music Series featuring Mercy Creek
Fri, Oct 23, 2026
5:30 PM – 8:30 PM
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Music
The Four Horsemen & Vulgar Display of Pantera are back to rock The Foundry!
Fri, Oct 23, 2026
8:00 PM
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Music
Five Old Gentleman (FOG) Live Music
Sat, Oct 24, 2026
3:00 PM – 5:00 PM
Come out to Blenheim Vineyards and enjoy live music from Five Old Gentleman (FOG) from 3-5pm. Free event, no ticket required.
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Special Event
Wine & Design with Monica Garrett Interiors
Sat, Oct 24, 2026
3:00 PM
Join Horton Vineyards for a Wine & Design event with interior designer Monica Garrett.
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Community
Heart of Virginia Artisans AUTUMN MARKET @ Hazy Mountain
Sun, Oct 25, 2026
11:00 AM – 4:00 PM
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Music
Sunday Jazz and Blues featuring John D'earth (last of the season!)
Sun, Oct 25, 2026
1:00 PM – 4:00 PM
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Art
Meet the Artist: Allie Kelly
Sun, Oct 25, 2026
2:00 PM – 4:00 PM
Blenheim Vineyards presents Meet the Artist featuring Allie Kelly. Enjoy local art paired with estate wines in a relaxed afternoon setting.
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Music
Homecoming: An Evening with Mariana Bell and Her Band
Sun, Oct 25, 2026
6:00 PM – 9:00 PM
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Tasting
Wine Wednesday
Wed, Oct 28, 2026
4:30 PM – 8:30 PM
Join King Family Vineyards every Wednesday for Wine Wednesday! The tasting room stays open until 8:30pm and food trucks are on-site from 4:30-7:30pm. Perfect evening to relax with a great glass of wine.
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Music
Friday Sundowner's Music Series featuring Wavelength (last of the season!)
Fri, Oct 30, 2026
5:30 PM – 8:30 PM
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Special Event
Outdoor Movie Night: Kelly's Heroes
Fri, Nov 6, 2026
6:30 PM
Enjoy an outdoor screening of the classic film Kelly's Heroes at Horton Vineyards. Bring blankets and chairs.
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Salute & Sip: A Military K9 Tribute
Sat, Nov 7, 2026
4:00 PM
A special tribute event honoring Military K9 units. Sip wines while celebrating the service of military working dogs.
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Other
Trail Run Club
Thu, Nov 12, 2026
6:00 PM – 7:00 PM
Join us for a trail run at Starr Hill Crozet! A fun weekly run through the trails, followed by cold craft beer.
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Art
The Art of Wine
Sat, Nov 14, 2026
4:00 PM – 7:00 PM
An event supporting The Arc of Piedmont, showcasing artwork from The Arc Studio paired with delicious wines from Grace Estate. Pop in any time between 4 & 7pm to enjoy mountain views, wine tastings, gorgeous artwork, and artmaking.
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Live Music: The Loya Brothers
Sat, Nov 14, 2026
5:00 PM – 7:00 PM
Enjoy live music from The Loya Brothers at Starr Hill Crozet. Great beer, great music, great vibes.
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Benefit
NCCF's Silver Starlight Opportunity Ball at Veritas
Sat, Nov 14, 2026
6:30 PM – 11:45 PM
An elegant evening benefiting the National Children's Center Foundation. Enjoy dancing, dining and wine at Veritas Vineyard. Tickets from $250.
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Music
Live Music: Forde Upshur
Sun, Nov 15, 2026
1:00 PM – 3:00 PM
Join us for an afternoon of live music from Forde Upshur at Starr Hill Crozet.
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Food Truck
Food Truck: PotLucky Cville
Tue, Nov 17, 2026
5:30 PM – 8:00 PM
PotLucky Cville food truck is at Starr Hill Crozet! Grab some delicious food to pair with your craft beer.
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Trivia
Trivia Night
Tue, Nov 17, 2026
7:00 PM – 9:00 PM
Test your knowledge at Trivia Night at Starr Hill Crozet! Form a team, grab a pint, and compete for bragging rights.
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Other
Trail Run Club
Thu, Nov 19, 2026
6:00 PM – 7:00 PM
Join us for a trail run at Starr Hill Crozet! A fun weekly run through the trails, followed by cold craft beer.
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Music
Live Music: Kurt Crandall
Sat, Nov 21, 2026
5:00 PM – 7:00 PM
Enjoy live music from Kurt Crandall at Starr Hill Crozet. Blues, swing, and great craft beer.
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Community
Heart of Virginia Artisans "giving thanks" MARKET @ Hazy Mountain
Sun, Nov 22, 2026
11:00 AM – 4:00 PM
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Food Truck
Food Truck: PotLucky Cville
Tue, Nov 24, 2026
5:30 PM – 8:00 PM
PotLucky Cville food truck is at Starr Hill Crozet! Grab some delicious food to pair with your craft beer.
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Trivia
Trivia Night
Tue, Nov 24, 2026
7:00 PM – 9:00 PM
Test your knowledge at Trivia Night at Starr Hill Crozet! Form a team, grab a pint, and compete for bragging rights.
More InfoOther
Trail Run Club
Thu, Nov 26, 2026
6:00 PM – 7:00 PM
Join us for a trail run at Starr Hill Crozet! A fun weekly run through the trails, followed by cold craft beer.
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Music
Live Music: Greg Ward
Fri, Nov 27, 2026
6:00 PM – 8:00 PM
Enjoy live music from Greg Ward at Starr Hill Crozet. Great beer, great music, great vibes.
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Music
Karaoke Night
Sat, Nov 28, 2026
7:00 PM – 10:00 PM
Sing your heart out at Karaoke Night at Starr Hill Crozet! Great craft beer, great songs, great times.
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Meet the Artists: Virginia Rieley & Eliza Evans
Sun, Nov 29, 2026
2:00 PM – 4:00 PM
Blenheim Vineyards presents Meet the Artists featuring Virginia Rieley & Eliza Evans. Enjoy local art paired with estate wines in a relaxed afternoon setting.
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Tasting
Port Tasting at Horton Vineyards
Sat, Dec 5, 2026
4:30 PM
Explore Horton Vineyards' celebrated port-style wines at this special tasting event.
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Special Event
New Year's Eve Black & White Ball at Veritas
Thu, Dec 31 – Fri, Jan 1, 2027
7:00 PM
Ring in the new year at Veritas with an elegant Black & White Ball featuring dinner, dancing and wine. $250/person.
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