Weekendr — Charlottesville Wine Country Events

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

Winery

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

Winery

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

Winery

Pippin Hill Farm & Vineyard

5022 Plank Rd, North Garden, Virginia 22959

Monday: Closed Tuesday: Open Wednesday: Open Thursday: Open Friday: Open Saturday: Open Sunday: Open

Pippin Hill Farm & Vineyards is a boutique culinary vineyard and all-season events venue set in the scenic foothills of the Blue Ridge Mountains within Virginia's Monticello Wine Region. The estate centers on award-winning estate-grown wines, including whites, reds, and rosés, paired with a garden-to-table culinary program in which the vineyard, garden, farm, and kitchen are seamlessly interwoven to serve fresh, local, and sustainable fare. Visitors can reserve table service in the Tasting Room and deepen their visit with experiences such as the Estate Tour & Tasting, cooking school classes, and other group offerings. The property also offers the Heritage Wine Club, a retail shop with Pippin-approved goods including its #PippinPups line, and gift cards, while a thoughtfully restored 1820s Crossroads Inn just down the hill lets guests extend their stay. Pippin Hill is also a full-service destination for custom-designed weddings and private events, complete with a dedicated culinary team and event services.

B&BDogsOutdoor Seating

Cidery

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

Winery

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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