
Upper Shirley Vineyards (Photo by Allison Dash courtesy Upper Shirley Vineyards)
Upper Shirley Vineyards
Charles City
Wine doesn’t simply pair with food, it pairs with experiences, and nowhere around the Richmond region is that more evident than at Upper Shirley. The far-reaching pastoral grounds include historic elements, views of the James River and even a bird sanctuary. Serving up nearly a dozen different wines, it is a place one could visit often. Most weekends they have live music and yoga on Sunday, perhaps topped off with a bubbly glass of their blanc de blancs. Maybe a group horseback ride is more your style, or perhaps you’d enjoy a guided bike ride on the Virginia Capital Trail complete with tastings and a luncheon, bike included. Special wine dinners are also a regular occurrence, and while lunch is available every day, don’t miss out on Chef Carlisle Bannister’s decadent Route 5 burger made with ground brisket and short rib.

Photo by Andrew Shurtleff courtesy Loving Cup Vineyard
Loving Cup Vineyard
North Garden
The area around Monticello in Albermarle County is one of many regions in Virginia with enough vineyards to fill a day trip. Loving Cup Vineyard stands out as the first in the state to be certified organic. Using beneficial insects, they crank out a number of minimally processed wines. Check out their Cayuga White, a lighter, more fruit-forward alternative to your typical chardonnay. The tasting room is open from April to December.
Barrel Thief
Richmond
Have you ever wondered where RVA wine professionals hang out on their days off? It’s here. Part wine shop, part wine bar, the well-curated and fast-changing wine list is often the inspiration for lists across the city. Friday evenings feature wine tastings, while Saturdays are dedicated to wine classes before the shop turns into the hippest jazz joint you’ve never heard of at night. Chef Ben Burakoff, also of the pop-up Pizza Bones and formerly of Sub Rosa Bakery, churns out nibbles to complement all that fermented grape juice.