Winery Events in Charlottesville, Virginia

Blenheim Vineyards

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

• Jay Pun & Jen Tal Live at BlenheimSat, Sep 12, 2026, 3 PM – 5 PM
• Tucker Wyatt Live at BlenheimSat, Sep 19, 2026, 3 PM – 5 PM
• Jeremy Huband Live at BlenheimSat, Sep 26, 2026, 3 PM – 5 PM

+ 5 more upcoming events →

Chisholm Vineyards

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

No upcoming events listed.

Eastwood Farm and Winery

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

• Porch Nights: Michael ClemThu, Sep 10, 2026, 5 PM – 8 PM
• Virginia Oyster & Wine with Live Music: John KellyFri, Sep 11, 2026, 5 PM – 8 PM
• Live Music: Brian FrankeSat, Sep 12, 2026, 12:30 PM – 3:30 PM

+ 13 more upcoming events →

Goat Rodeo Comedy Co.

Goat Rodeo Comedy Co. presents bold, character-driven long-form improv at monthly shows in Charlottesville and beyond, with scenes and stories built entirely from an audience suggestion. Shows are staged at Vinegar Hill Theatre.

• Back to Cool Improv NightSat, Sep 19, 2026, 7 PM

Hark Vineyards

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

• Sweet Jane's Kitchen & Midnight Buzz BandSat, Sep 12, 2026, 4 PM – 7 PM
• Sharif MusicSun, Sep 13, 2026, 2 PM – 5 PM
• Catching Fish & Chips & Mercy Creek MusicSat, Sep 19, 2026, 4 PM – 7 PM

Jefferson Vineyards

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

No upcoming events listed.

Oakencroft Farm & Winery

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.

Roslyn Farm & Vineyard

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.

Three Notch'd Craft Kitchen & Brewery

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.