CHARLOTTESVILLE WINE COUNTRY

Discover live music, tastings, festivals & food trucks at wineries, breweries, and cideries across the Monticello AVA.

Stay in the Loop

Get weekly updates on events, new venues, and wine country happenings — delivered to your inbox.

Find Events

221 events — All upcoming

Coming up next

Featured Venues

Wineries, breweries & distilleries near Charlottesville

WineryMerrie Mill Farm & Vineyard logo

Merrie Mill Farm & Vineyard

594 Merrie Mill Farm, Keswick, VA 22947
Monday: 10:30am-5:30pm Tuesday: Closed Wednesday: Closed Thursday: 10:30am-5:30pm Friday: 10:30am-5:30pm Saturday: 10:30am-5:30pm Sunday: 10:30am-5:30pm

Merrie Mill Farm & Vineyard is a family-owned winery and tasting room destination in Keswick, Virginia, near Charlottesville. Founded by Guy and Elizabeth Pelly, it reimagines the tasting room experience by pairing warm, approachable hospitality with a playful, maximalist setting known for its bold interior design and unexpected artwork. The tasting room features two copper bars in a lofted interior, with multiple terraces and lawns overlooking the vineyards and views up the South West Mountains. Guests can make reservations for wine tastings and lovingly prepared food, sample estate-grown wines such as the rose, Viognier, and white blend, and join the winery's club. Merrie Mill also hosts special events and live music, including Friday Sundowners and Sunday blues and jazz, and offers overnight stays next door at the two-bedroom Clementine Cottage with views over the vineyard.

Outdoor SeatingWeddingsB&B

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

WineryCunningham Creek Winery logo

Cunningham Creek Winery

3304 Ruritan Lake Road, Palmyra, VA 22963
Sunday: 12pm-6pm Thursday: 12pm-6pm Friday: 12pm-6pm Saturday: 12pm-6pm

Cunningham Creek Winery & Brewery is a family-owned and operated small-lot winery and brewery on the Monticello Wine Trail in Fluvanna County, Virginia, about 20 minutes from Jefferson's Monticello, 30 minutes from Charlottesville, and 10 minutes from Lake Monticello. The boutique winery produces only about 2,000 cases a year of finely crafted French varietals and Bordeaux-style blends, all made on site by winemaker Bruce, and has earned numerous honors including multiple Virginia Governor's Cup and Monticello Cup medals. It is also the first brewery in its community, pouring a selection of craft beers on tap alongside the wines. Visitors can taste in the air-conditioned tasting room or relax in the newly expanded outdoor seating, and the winery is family, dog, and picnic friendly, with a dog park where pups can run off-leash. Regular events include live music on Saturday nights and team trivia on the third Thursday of each month.

DogsFamily FriendlyOutdoor Seating

WineryDucard logo

Ducard

40 Gibson Hollow Ln, Etlan, Virginia 22719
Open Daily, Year-round Monday – Thursday: 12-5 PM Friday: Summer (April – October) 12-9pm with live music starting at 5:30 Friday: Winter (Nov – March) 12-6pm Saturday: 12-6pm with live music starting at 2:30 Sunday: 12-6 PM

DuCard Vineyards is an authentic farm winery in Etlan, Madison County, Virginia, set against the eastern slope of Shenandoah National Park near Old Rag Mountain. Its wines are handmade on site using traditional methods from estate grapes grown at three local Madison County vineyard sites, an approach that has earned the winery gold medals and 90-plus point ratings along with recognition as a top-rated Central Virginia winery and a leader in environmental sustainability. Visitors can settle in for full-service wine flights of reds and whites served in crystal glassware at their table, or enjoy current-release and library wines by the bottle. The setting offers comfortable seating at mountain-view tables on the back lawn, a stream-side deck, a pavilion, and an air-conditioned event room, all surrounded by scenic Blue Ridge views. DuCard is family-friendly, dog-friendly, and picnic-friendly, with live music on weekends and a calendar of special events, plus optional reservations and space for private gatherings.

DogsFamily FriendlyOutdoor Seating

BreweryStarr Hill Brewery - Crozet logo

Starr Hill Brewery - Crozet

5391 Three Notch'd Rd, Crozet, VA 22932
Monday | 3–8 PM Tuesday | 3–10 PM Wednesday | 3–10 PM Thursday | 12–10 PM Friday | 12–10 PM Saturday | 11 AM–10 PM Sunday | 11 AM–8 PM

Starr Hill Brewery is an independent, regional craft brewery that was born in a Charlottesville music hall in 1999 and has been brewing beer in Virginia ever since. Its Crozet location serves as the brewery's production home and taproom, one of six Starr Hill spots that also include Charlottesville, Lynchburg, Roanoke, Richmond, and Tysons. Visitors to the Crozet taproom can enjoy a rotating lineup of the brewery's craft beers, from year-round favorites to seasonal and limited releases, in a relaxed setting that nods to the brewery's roots in live music. The taproom welcomes guests for casual visits and can also host private events and gatherings. Beyond the beer, Starr Hill offers branded apparel and merchandise, gift cards, and regular news about new brews and label designs.

DogsFamily FriendlyOutdoor Seating

WineryHazy Mountain logo

Hazy Mountain

240 Hazy Mountain Ln., Afton VA 22920
Sunday: 11:00 am - 6:00 pm Monday: 11:00 am - 6:00 pm Tuesday: 11:00 am - 6:00 pm Wednesday: 11:00 am - 6:00 pm Thursday: 11:00 am - 6:00 pm Friday: 11:00 am - 8:00 pm Saturday: 11:00 am - 8:00 pm

Hazy Mountain is a family-owned winery in the Blue Ridge Mountains of Virginia that produces wine from its own estate vineyards. With 86 acres under vine across two sites in Afton and Swoope, the winery proudly represents both the Monticello and Shenandoah Valley AVAs, aiming to let the vineyards speak for themselves and tell the story of what their distinctive soils have to offer. Guests can personalize their visit with guided tastings, offered seven days a week in the tasting room, with private guided tastings available upon request. The winery also offers a tiered wine club with four membership levels, plus tasting room and online shop discounts, for those who want to enjoy more Hazy Mountain at home. Beyond tastings, Hazy Mountain hosts weddings and private events in its dedicated vineyard event spaces and maintains a calendar of ongoing happenings throughout the year.

Family FriendlyWeddings

The Cville Weekendr Newsletter

Wine country events, delivered to your inbox weekly.

Live music, tastings, and festivals at wineries, breweries, and cideries around Charlottesville. No spam; unsubscribe anytime.

Ongoing & multi‑week events

Longer-running happenings — exhibits, series, and season-long events you can catch any week.