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Merrie Mill Farm & Vineyard
location_on Keswick
language Website
Experience: Set off on a safari-inspired escapade in a vintage Land Rover, cruising through the 12-acre vineyard and along the creek. After you explore the fields, the winery sets up a tented picnic with a spread of sandwiches, salad, charcuterie boards, and seven wines to sample. Up to seven bottles of wine are included in the three-hour excursion.
Stay: Located on the vineyard, the Clementine Cottage is a cozy pink house with two bedrooms and a spacious patio. Order room service from the nearby tasting room for salads, sandwiches, and pizza dropped at your door.
Distance from DC: Two hours and 15 minutes
King Family Vineyards
location_on Crozet
language Website
Experience: Tailgating gets a posh makeover during Sunday polo matches. Reserve a spot with a tent to dine on food-truck fare and sip wine. A golf cart selling bottles circulates about, and there are also field-side pours. Ready to play? The vineyard hosts a boozy polo school Tuesday through Saturday, where you can do a tasting and take a class, no experience necessary.
Stay: Iris Inn, about 15 minutes from the winery, has multiple lodging options. Book a stay in the main inn or, for additional solitude, check out the intimate cottages and cabins with views of the valley.
Distance from DC: Two hours and 30 minutes
Chatham Vineyards
location_on Machipongo
language Website
Experience: Tour operator Southeast Expeditions leads kayaking trips starting and ending at the wharf in Bayford, with a stop at this winery on Virginia’s Eastern Shore. Paddle for about 45 minutes past watermen and marine birds (you might see a bald eagle) before docking at the vineyard for a tour and tasting. Each solo participant or pair gets a bottle of wine to take home.
Stay: For accommodations near the waterfront, head to Hotel Cape Charles, about 25 minutes from the kayaking drop-off point. The boutique hotel has modern rooms plus free bicycles and beach chairs.
Distance from DC: Four hours
Keswick Vineyards
location_on Keswick
language Website
Experience: The vineyard has a wine-themed mini-golf course with nine holes, ideal for a winery day with kids in tow. Each stop has a small table so you can put down your drink while you putt, and a bar is sometimes set up by the course for refills. Pets are also allowed at the winery, and there’s a fenced area for dogs to play.
Stay: Less than ten minutes from the winery, luxury resort Keswick Hall offers guests a well-appointed spa; an up-scale restaurant; and an infinity pool with views of the bucolic surroundings.
Distance from DC: Two hours and ten minutes
Veritas Vineyard
location_on Afton
language Website
Experience: Explore the vineyard and surrounding farmland during a horseback-riding session with tour operator Indian Summer Guide Services. Rides are an hour and a half, with views of the Blue Ridge Mountains. Once you dismount, venture to the tasting room or brick terrace for wine, cheese, and charcuterie boards. The tour company also offers the occasional sunset ride.
Stay: You don’t need to go far to find a spot to slumber: Farmhouse at Veritas is a bed-and-breakfast next to the vineyard with six bedrooms in the main house and another two in a private cottage.
Distance from DC: Two hours and 45 minutes
