Winery Events in Keswick & Eastern Albemarle

Castle Hill Cider

Castle Hill Cider is an artisanal cidery and premier event venue set on 650 acres of picturesque countryside in Keswick, just outside Charlottesville, Virginia. The estate is best known as a stunning wedding and event destination, offering a curated collection of spaces that range from intimate gatherings to large celebrations. Couples and guests can choose among settings such as the Terrace, Linden Grove, sweeping lawns and mountain views, a reception barn, a loft, and private suites for getting ready. The property pairs its scenic Virginia landscape with the craft of cider making, creating a backdrop for memorable weddings and special occasions. Castle Hill Cider is currently booking events into 2026 and 2027, with limited dates still available in 2025.

Outdoor SeatingWeddingsB&B

No upcoming events listed.

Cunningham Creek Winery

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

No upcoming events listed.

Keswick Vineyards

Keswick Vineyards is a family-owned and operated winery near Charlottesville, Virginia, in the Monticello wine region. Founded in 2000, its first vintage earned the honor of Best White Wine in America at the Atlanta International Wine Summit in 2002, and the winery has since gone on to win two Virginia Governor's Cups along with numerous Gold, Double Gold, and Platinum awards. The family-friendly tasting room offers an elevated food menu through its in-house kitchen, Barrel & Board, plus a miniature golf course, a dog park, and live music. Visitors can taste the winery's wines, join the wine club, and attend regular events such as the Wine Down Wednesday live music series. The estate is also a popular setting for weddings and is a proud partner of Virginia Tourism.

DogsFamily FriendlyOutdoor Seating

• Wine Down Wednesday – The UnsuitablesWed, Jul 15, 2026, 5:30 PM – 8:30 PM
• Live Music – Big Gavel Country BandSat, Jul 18, 2026, 1 PM – 4 PM
• Wine Down Wednesday – South Canal Street BandWed, Jul 22, 2026, 5:30 PM – 8:30 PM

+ 4 more upcoming events →

Merrie Mill Farm & Vineyard

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

• Friday Sundowner's Music Series featuring Blane Perry and Bob LedbetterFri, Jul 17, 2026, 5:30 PM – 8:30 PM
• Sunday Jazz and Blues featuring Elliot CurrieSun, Jul 19, 2026, 1 PM – 4 PM
• Friday Sundowner's Music Series featuring Jacob Paul AllenFri, Jul 24, 2026, 5:30 PM – 8:30 PM

+ 29 more upcoming events →

Southwest Mountains Vineyards

Southwest Mountains Vineyards is an estate winery in Keswick, Virginia, just outside Charlottesville in the rolling hills of the Monticello AVA. At the heart of the property is the Tasting Barn, a fully restored 1903 structure that now houses the tasting room and pairs historic character with an understated, modern approach to hospitality. The estate vineyards are cultivated in the area's distinctive soils and climate, and the wines are made with a minimalist approach in the cellar to reflect a sense of place. Visitors can choose from guided tasting flights or relaxed by-the-glass visits, with both intimate indoor seating and open-air tables overlooking the vineyard, and reservations are recommended though walk-ins are welcome. Beyond tastings, SMV offers The Glade, a bookable hiking, wine, and lunch experience along an estate trail, as well as private events, seasonal festivals and winemaker dinners, and a wine club with seasonal selections and member benefits.

Outdoor SeatingPicnicOutside Food

• Guest Star Hike with BoelaSat, Jul 25, 2026, 12 PM – 2 PM
• Blooms 4 Good Floral WorkshopSun, Jul 26, 2026, 1 PM – 5 PM
• Summer Culinary Series: Pours & Pasta (Thursday)Thu, Jul 30, 2026, 6:30 PM – 9 PM

+ 1 more upcoming event →