Drawing on a rich history, Blenheim Vineyards grows four different blocks of vines and offers a variety of wines. In partnership with founder Dave Matthews, the winery practices philanthropy by supporting World Central Kitchen, which offers food relief following natural disasters. Blenheim hosts regular special events featuring food trucks, a mobile bookstore, and special culinary delights. Make a reservation and order a catered box meal or bring your own picnic.

• Thursday to Sunday
• Special open events
• Line of wine to combat world hunger

Delfosse Vineyards has won awards for both its wines and special event hosting. The grounds are complete with views to take your breath away. Take a walk along the unique terrace-style vineyards. End the day at a historical log cabin that provides accommodations you’ll find nowhere else.

• Wednesday-Sunday
• Dogs and picnics welcome
• Historical log cabin accommodations

Offering a full experience for the whole family, Eastwood Farm and Winery has wines, snacks and non-alcoholic beverages. Take the kids or your partner on a hike of the vineyards, and bring a picnic to enjoy at any point. Enjoy weekly music, monthly art exhibitions, and plenty of special events like wine and yoga, food trucks, and sunset celebrations.

• Wednesday to Sunday
• Weekly music
• Art exhibitions

Featuring modern architecture and an intimate setting, Gabriele Rausse Winery is a popular wine destination whose labels you’re likely to see in stores across the country. Outdoor tastings are available Thursday, Friday, and Sunday. Beyond wine, the winery offers a wide variety of products including raw honey and Sicilian olive oil.

• Outdoor tastings only
• Open Thursday, Friday, and Sunday
• Variety of goods

Open Saturday and Sunday, Hardware Hills Vineyard offers spacious outdoor seating areas and a variety of wines, including sangria. Come on the right weekend to catch music and special events. Just look for the blue gate and sign!

• Saturday and Sunday
• Seasonal sangria
• Spacious outdoor seating

Organic is the name of the game at Loving Cup, and there’s a USDA certificate to prove it. The winery currently offers wine and sangria by the glass and bottle as well as flight tastings. Bring your pet, bring a picnic, enjoy the comfortable atmosphere, and learn about organic farming while you’re there.

• Certified organic
• Pet and picnic friendly
• Sangria

Featuring environmentally friendly gravity-flow production, Lovingston Winery focuses on small details to yield big results. The family farm features traditional as well as South African varietals. Schedule an overnight stay in The Cabin at Lovingston Winery or The Farmhouse at Lovingston Winery. 

• Open Saturday and Sunday
• Environmentally friendly production
• Intimate

Owned by a winemaker who trained at and owns a successful vineyard in Burgundy, France, Michael Shaps Wineworks offers a variety of tastes and experiences. Visit the vineyard tasting room for local wines as well as the Maison Shaps Burgundy label, imported from the Burgundy vineyard. Check out the warehouse in Charlottesville for the domestic and imported Shaps line as well as specialty wines imported just for that location.

• Traditional Burgundy-trained owner
• Multiple locations, each with a tasting room
• Domestic and imported wines available

Sprawling over 5,000 acres, Mt. Ida Farm and Vineyard offers several jaw-dropping venues, ceremony sites and overnight accommodations. Just going for the day? Visit the tasting room and taphouse. Offering picnic-style snacks Monday to Thursday and a full kitchen menu Friday to Sunday, there is always something tasty to pair with the house-brewed craft beers and estate-grown wines.

• Wine and craft beer
• Fireplace terrace

It’s not only the award-winning wines and exquisite mountain views that have helped build Pippin Hill’s reputation as one of the Charlottesville area’s premiere wineries. It’s also the farm-to-table cuisine that rounds out a complete culinary experience. The seasonal tasting room menu features locally grown and produced fare like roasted cauliflower with smoky butter, cilantro, sherry vinegar and granola and grass-fed beef sliders with aged cheddar, smoked pepper and pickled shallot.

• Eight medals in the 2021 Governor’s Cup
• Covered outdoor seating areas
• Pristine mountain views

The Trump Winery is larger than life yet still welcoming. Taste reds and whites, and enjoy a treat from the seasonal menu. Bring your own blanket and chairs for an outdoor experience. For a truly Trumpian experience, stay overnight at over-the-top luxurious Albemarle Estate, where even your pet will be pampered with a plush dog bed, fresh bottled water, and plenty of toys.

• Wednesday-Monday
• Albemarle Estate rooms available
• Full seasonal menu

Wisdom Oak offers outdoor, self-guided wine tastings. Reservations are strongly encouraged. This dog-friendly location offers a seasonal menu to pair with its best wines, which are made in small batches to ensure quality. There are also three separate sites on location for private events.

• Thurs-Sun
• Three sites for private events
• Outdoor seating only