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Events › Charlottesville

Winery Events in Charlottesville, Virginia

Charlottesville sits at the center of the Monticello AVA, with tasting rooms, urban wineries, and cideries minutes from downtown. Live music, trivia nights, and tastings run all week — no long drive required.

Upcoming events in Charlottesville

Trump Grand Tastings
Tasting

Trump Grand Tastings

Trump Winery
Sat, Jul 18, 2026
12:00 PM – 1:00 PM

Discover the best of Trump Winery with our exclusive Trump Grand Tasting Experience—a guided, one-hour tasting in the new Meritage Barrel Room featuring a curated flight of six estate-grown wines. Includes a souvenir Trump Winery wine glass and small-group hospitality for up to 16 guests. Advance reservations required. Limited availability.

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Trump Grand Tastings
Tasting

Trump Grand Tastings

Trump Winery
Sat, Jul 25, 2026
12:00 PM – 1:00 PM

Discover the best of Trump Winery with our exclusive Trump Grand Tasting Experience—a guided, one-hour tasting in the new Meritage Barrel Room featuring a curated flight of six estate-grown wines. Includes a souvenir Trump Winery wine glass and small-group hospitality for up to 16 guests. Advance reservations required. Limited availability.

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Meet the Artist: Richard White
Art

Meet the Artist: Richard White

Blenheim Vineyards
Sun, Jul 26, 2026
2:00 PM – 4:00 PM

Join us in the tasting room at Blenheim Vineyards and meet the artist, Richard White. His artwork will be on display and available for purchase. We will have snacks and wine for sale by the glass, bottle, and flights.

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Mimosas & Masterpieces
Art

Mimosas & Masterpieces

Trump Winery
Fri, Jul 31, 2026
10:00 AM – 12:30 PM

Start your morning with creativity, cider, and vineyard views at Trump Cidery's Mimosas & Masterpieces, a guided paint-and-sip experience on the cidery patio. Each ticket includes guided paint instruction from a professional artist, all painting materials, a complimentary welcome mimosa or bellini crafted with Trump Cider Apple-achian, curated light brunch fare, and your completed artwork to take home.

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Field Day: Susie & The Pistols
Music

Field Day: Susie & The Pistols

Blenheim Vineyards
Sun, Aug 2, 2026
3:00 PM – 5:00 PM

Join us for Field Day at Blenheim Vineyards and enjoy an easygoing afternoon of live music, vineyard views, and time well spent together. Susie & The Pistols 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.

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Meet the Artist: Nicole Singleton
Art

Meet the Artist: Nicole Singleton

Blenheim Vineyards
Sun, Aug 30, 2026
2:00 PM – 4:00 PM

Join us in the tasting room at Blenheim Vineyards and meet the artist, Nicole Singleton. Her photographs will be on display and available for purchase. We will have snacks and wine for sale by the glass, bottle, and flights.

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Field Day: The Norms
Music

Field Day: The Norms

Blenheim Vineyards
Sat, Sep 5, 2026
3:00 PM – 5:00 PM

Join us for Field Day at Blenheim Vineyards and enjoy an easygoing afternoon of live music, vineyard views, and time well spent together. The Norms will be playing live from 3-5 PM under the tent overlooking the vineyard.

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Meet the Artist: Frank Phillips
Art

Meet the Artist: Frank Phillips

Blenheim Vineyards
Sun, Sep 27, 2026
2:00 PM – 4:00 PM

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

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Field Day: Small Town Rodeo
Music

Field Day: Small Town Rodeo

Blenheim Vineyards
Sat, Oct 3, 2026
3:00 PM – 5:00 PM

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.

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Meet the Artist: Allie Kelly
Art

Meet the Artist: Allie Kelly

Blenheim Vineyards
Sun, Oct 25, 2026
2:00 PM – 4:00 PM

Join us in the tasting room at Blenheim Vineyards and meet the artist, Allie Kelly. Her artwork will be on display and available for purchase. We will have snacks and wine for sale by the glass, bottle, and flights.

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Venues in Charlottesville

WineryBlenheim Vineyards logo

Blenheim Vineyards

31 Blenheim Farm, Charlottesville, VA 22902
Monday: 11am-5:30pm Tuesday: Closed Wednesday: Closed Thursday: 11am-5:30pm Friday: 11am-5:30pm Saturday: 11am-5:30pm Sunday: 11am-5:30pm

Blenheim Vineyards is a family-owned winery located about 20 minutes from downtown Charlottesville, Virginia, set in a scenic, rustic landscape of rolling hills and grapevines. The winery farms several distinct vineyard sites, including its Blenheim, Claim, Deer Ridge, and Seaview vineyards, each with its own terroir and soils, and takes a minimalist, sustainable approach in the cellar to let the fruit speak for itself under winemaker Kirsty Harmon. Visitors are welcome in the tasting room, a warm wooden space with vaulted ceilings and large windows overlooking the vineyard, where they can sample Virginia-grown wines; reservations are not required, though guided tastings are recommended on Saturdays. The winery is known for its annual Painted Series, a pair of limited-edition red and white wines whose labels are created or curated by musician Dave Matthews. Blenheim also offers a wine club with three releases per year and a calendar of tastings and events throughout the season.

Outdoor SeatingPicnic

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WineryChisholm Vineyards logo

Chisholm Vineyards

1135 Clan Chisholm Lane, Earlysville, VA, 22936
Fridays, Saturdays & Sundays 12-5pm

Chisholm Vineyards is a family-owned, woman-owned and operated winery located on Adventure Farm near Charlottesville, Virginia, within the Monticello AVA, where the Chisholm family has owned and worked the 500-acre property since 1950. The winery produces 100 percent estate-grown Virginia wine, crafting small-lot, award-winning bottlings in a low-intervention style that lets the grape, terroir, and climate define each unique vintage. Visitors can settle into a variety of settings, from the tasting room to an outdoor pavilion, a wisteria arbor, or expansive lawns framed by Blue Ridge Mountain views, and the property is both child- and dog-friendly. Wines are available on-site, by curbside pickup, and via shipping to many states, and the winery offers a no-fee wine club with member discounts, exclusive events, and perks. The grounds also serve as an event venue for weddings, rehearsal dinners, and private gatherings, and host a mobile Finnish wood-fired sauna and cold plunge experience for relaxation and celebrations.

DogsOutdoor SeatingB&B

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WineryEastwood Farm and Winery logo

Eastwood Farm and Winery

2531 Scottsville Road, Charlottesville, VA 22902
Monday: 12pm-5pm Tuesday: 12pm-5pm Wednesday: 12pm-5pm Thursday: 12pm-8pm Friday: 12pm-8pm Saturday: 12pm-8pm Sunday: 12pm-5pm

Eastwood Farm and Winery is a women-owned, multi-generational winery and wine incubator located just five miles from downtown Charlottesville, Virginia, on the Monticello Wine Trail. Its tasting room sits in a peaceful country setting near the University of Virginia and Monticello, and the winery pours award-winning wines, including Governor's Cup gold medal winners, alongside housemade beers and ciders inspired by its seasonal farm. Guests can pair their wine with a full lunch and dinner menu created by the winery's chefs, and enjoy ample indoor and outdoor seating including a covered patio, with the winery open seven days a week and late on Thursday through Saturday. Eastwood is dog-friendly and family-friendly, offering non-alcoholic options such as popular juice flights, and it hosts live music and events throughout the week. The business also operates a second location, the Virginia Wine Collective, an urban wine production facility and tasting room about three miles away that serves thin-crust pizzas, shareable plates, winemaker flights, and beers on tap, and is open to guests 21 and over.

DogsFamily FriendlyOutdoor Seating

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WineryHark Vineyards logo

Hark Vineyards

1465 Davis Shop Rd, Earlysville, VA 22936
Monday: 12pm-5pm Tuesday: Closed Wednesday: Closed Thursday: 12pm-5pm Friday: 12pm-8pm Saturday: 12pm-8pm Sunday: 12pm-6pm

Hark Vineyards is a family-owned winery in Virginia built on the belief that beautiful views and delicious wine can bring people together. The wines are authentically Virginian, produced on site from grapes grown on the estate, and visitors can see the production space directly from the tasting room. Set across an 80-acre estate, the winery invites guests to sample thoughtfully crafted small-batch wines that aim to stay true to vintage and terroir. Visitors can take in the scenic views, cozy up to a fire, and spend a relaxed afternoon in the tasting room. Hark has earned notable recognition, including being one of only two wineries to take home five Gold medals in the 2026 Virginia Governor's Cup for wines such as its Roussanne, Cabernet Franc, Petit Verdot, and estate blends Ember and Spark.

EV Charging

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WineryJefferson Vineyards logo

Jefferson Vineyards

1353 Thomas Jefferson Parkway, Charlottesville, VA 22902
Sunday–Thursday: 11:00 AM – 6:00 PM Friday–Saturday: 11:00 AM – 7:30 PM

Jefferson Vineyards is a historic winery just 10 minutes from Charlottesville, set in the rolling foothills of the Blue Ridge Mountains at the heart of Virginia wine country. The site carries deep winemaking roots, as nearly 250 years ago Thomas Jefferson and Philip Mazzei began growing grapes on this very land in pursuit of Jefferson's dream of establishing American winemaking. The vineyard neighbors Monticello, Jefferson's mountaintop home, and Highland, the nearby estate of President James Monroe. Visitors can sample the winery's award-winning wines, which range from delicate and refreshing to elegant, full-bodied, and rich, in the tasting room open daily. Guests can also shop the wines, join a wine club, and soak in the scenery and history of one of Virginia's earliest wine sites.

DogsFamily FriendlyOutdoor Seating

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WineryKnights Gambit Vineyard logo

Knights Gambit Vineyard

2218 Lake Albemarle Road, Charlottesville, VA 22901
Thursday: 5pm-8pm Friday: 2pm-8pm Saturday: 12pm-8pm Sunday: 12pm-6pm

Knight's Gambit Vineyard is a family-run winery at 218 Knole Farm Lane in Charlottesville, Virginia, where guests come to enjoy estate-grown wines amid vineyard and mountain views. Visitors to the tasting room can sample a flight of all six estate-grown wines, or enjoy their favorites by the glass or bottle. The property features a furnished Cabana Deck, a semi-private micro venue with comfy couches, airy curtains, and seating for up to 20, available to rent for parties, day dates, and family gatherings. The winery also hosts live music and can accommodate weddings and larger private parties. Knight's Gambit is open Thursday through Sunday, with afternoon and evening hours that stretch later toward the weekend.

DogsWeddingsOutdoor Seating

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WineryMichael Shaps Wineworks logo

Michael Shaps Wineworks

1650 Harris Creek Rd, Charlottesville, VA
Monday: 11am-5pm Tuesday: 11am-5pm Wednesday: 11am-5pm Thursday: 11am-5pm Friday: 11am-5pm Saturday: 11am-5pm Sunday: 11am-5pm

Michael Shaps Wineworks is a winery nestled in the woods just south of Charlottesville, Virginia, offering a tasting experience that blends Old World tradition with Virginia terroir. Founded in 2007 by acclaimed winemaker Michael Shaps, the winery is known for producing small-batch, age-worthy wines that emphasize balance, varietal integrity, and regional character. Guests can enjoy seated tastings featuring both the Michael Shaps Virginia wines and his imported Maison Shaps Burgundy selections, which are bottled in Meursault, France and shipped directly to the winery. The rustic-industrial tasting room provides ample indoor and outdoor seating, including a spacious deck, a stone patio, and an expansive front lawn for relaxed sipping in nature, while wine club members can retreat to the upstairs Loft for more intimate gatherings. With flights, glasses, and bottles to enjoy, a wine club offering curated Virginia and Burgundy shipments, and curated events throughout the year, Michael Shaps Wineworks celebrates craftsmanship and the evolving story of Virginia wine.

Outdoor Seating

No upcoming events listed.

Winery

Monte Piccolo Farm and Distillery

3135 Blandemar Drive, Charlottesville, VA 22903
By appointment only

Monte Piccolo Farm and Distillery is a small farm-to-bottle distillery that grows its own fruit and distills it into fine spirits in a true organic operation. The distillery specializes in fresh fruit "eau de vie" style brandies, made from hand-harvested, tree-ripened fruit whose essences are captured in the glass through distillation. It is also known for its varietal gins, with the makers describing themselves as the only distillery focusing on the unique characteristics of each individual species of juniper. Distillery tours and tastings are offered by appointment only, with the tasting room and bar set against scenic farm views and able to host small groups. Visitors interested in the craft of growing and distilling can arrange a visit through the distillery's contact page to sample the brandies and gins firsthand.

No upcoming events listed.

WineryOakencroft Farm & Winery logo

Oakencroft Farm & Winery

1455 Oakencroft Circle, Charlottesville, VA 22901
Thur, 1 PM - 8 PM Fri – Sun, 11 AM – 5 PM

Oakencroft Farm & Winery is a sustainability-focused farm and winery about 10 minutes from downtown Charlottesville, Virginia. Built around regenerative farming, the estate tends its soil and vineyards to restore biodiversity, capture carbon, and preserve farmland, working with some of the oldest vines in Virginia to craft expressive, small-batch estate wines. The Tasting Room offers a serene escape where guests can sample these wines alongside a rotating selection of sustainably produced wines from acclaimed regions worldwide, paired with a seasonal menu of locally sourced cheese and charcuterie boards, light bites, and handmade sweets. Visitors can also join the farm and wine clubs for seasonal allocations of estate wines, grass-finished beef, and other local products, or take part in experiences like monthly farm walks. The property includes flexible event spaces, including the Tasting Room, the Fox Den, and the sustainably built Oakencroft Center, making it a venue for weddings, retreats, meetings, and private gatherings in harmony with nature.

Outdoor SeatingB&B

No upcoming events listed.

CideryPotter's Craft Cider logo

Potter's Craft Cider

1350 Arrowhead Valley Road, Charlottesville, VA 22903
Monday-Wednesday: Closed Thursday: 3:00 PM - 9:00 PM Friday: 12:00 PM - 9:00 PM Saturday: 12:00 PM - 9:00 PM Sunday: 11:00 AM - 8:00 PM

Potter's Craft Cider is a Virginia cidery whose tasting room sits just minutes south of Charlottesville. The cider is made with local Virginia apples using traditional production methods, resulting in a crisp, tart, and refreshing pour with a pronounced fruit aroma, and it is both zero sugar and zero gluten. The tasting room features 10 ciders on draft, giving visitors plenty to sample and compare. Every weekend the space comes alive with live music and local food trucks, making it a lively spot to gather with friends. Guests must be 21 or older to visit.

DogsOutdoor SeatingWeddings

No upcoming events listed.

WineryRoslyn Farm & Vineyard logo

Roslyn Farm & Vineyard

100 Roslyn Heights Road, Charlottesville, VA 22901
Sundays 2:00 PM – 6:00 PM Mondays 4:30 PM – 7:00 PM Tuesdays 4:30 PM – 7:00 PM Private tastings available upon request

Roslyn Farm & Vineyard is an agritourism farm estate, vineyard, and winery set in the rolling hills of Central Virginia, just outside Charlottesville near the University of Virginia. Originally built in 1938 as a European-style manor house, the property evokes the French countryside while radiating Southern charm through its architecture, landscape design, and historic gardens. After being acquired in 2015, it was renamed and revitalized into a vibrant farm estate that now blends a vineyard and winery with an equestrian center, farm lodging, and a wedding and event venue. Open to the public, the farm hosts wine tastings and live music on Sundays, Mondays, and Tuesdays, with private tastings available by request. Family-friendly and welcoming to both locals and travelers, Roslyn Farm offers a one-of-a-kind rural retreat in the heart of Virginia wine country.

B&BFamily FriendlyWeddings

No upcoming events listed.

BreweryThree Notch'd Craft Kitchen & Brewery logo

Three Notch'd Craft Kitchen & Brewery

520 2nd St SE, Charlottesville, VA 22902
Mon-Thu: 11am-10pm Fri: 11am-11pm Sat: 10am-11pm Sun: 11am-9pm

Three Notch'd Craft Kitchen & Brewery is part of the Three Notch'd Brewing Co. family, the Charlottesville-born brewery founded in 2013 by three friends who believed great beer should be fresh, flavorful, and shared. The name comes from the historic Three Notch'd Road that once connected communities across Virginia, and the brewery became known for award-winning beer, creative food, and welcoming gathering spaces. At the Craft Kitchen & Brewery, rotating taps pour fan favorites, seasonal releases, and small-batch experiments, from crisp lagers to bold IPAs, alongside chef-driven comfort food and canned cocktails. Many locations brew on site just steps from where the beer is poured, and select spots also feature Three Notch'd Distilling Co. spirits used in the cocktail program. It is a relaxed, family-friendly spot to grab a pint, share a meal, catch a game, or celebrate with good company.

Family Friendly

No upcoming events listed.

WineryTrump Winery logo

Trump Winery

385 Albemarle House Drive, Charlottesville, VA 22902
Wednesday–Monday, 11:00 AM – 5:00 PM. Closed Tuesdays, Easter, Thanksgiving, Christmas Eve, Christmas Day, New Year's Eve, and New Year's Day.

Step into the Grand Hall Tasting Room and explore a world of award-winning wines in the heart of Virginia's wine country. Enjoy curated tastings, seasonal menu offerings, and an inviting atmosphere where luxury meets relaxation. Whether you're a seasoned connoisseur or a casual taster, every visit is an unforgettable experience of craftsmanship and elegance.

DogsFamily FriendlyOutdoor Seating

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Other areas

Crozet & Western Albemarle · Afton & Nelson County · Keswick & Eastern Albemarle · Barboursville, Orange & Madison · Scottsville & Southern Albemarle · Greene & Northern Foothills