Located in Centerville, Virginia this winery is the closest to DC but feels a world away. The pastoral setting has plenty of space for kiddos to roam. Grab a glass or two and sit on the porch while the littles run around this wide-open space reserved for families. Take a walk as a family and explore the old homestead before your wine tasting. You can reserve a picnic table prior to arriving or find a spot to spread a picnic blanket. Right now, this venue is outdoors only and masks are required.

Long-cited as DC’s top family-friendly winery, Barrel Oak unfolds against the backdrop of the beautiful Virginia Piedmont countryside, just a hop and a skip (one hour) from the District. Owners Brian and Sharon work hard to create a community atmosphere by welcoming parents with kids, hikers, bikers, and travelers from the other side of the globe. Children love the all-inclusive, pet-friendly atmosphere; adults love the expansive patio views and whimsical décor.

If you’re looking for a majestic, comfortable place where the entire family can lounge around together, Early Mountain Vineyards is your place. Located just an hour and a half away from downtown DC, kids can even join in the tasting with Okencroft Farm Juices, made from wine grapes, but without the alcohol. Reservations are strongly recommended. You can reserve a patio seat or picnic table online.

This really is a little spot of paradise located right in Clifton, VA. Pack up a picnic lunch, plan a hike at the nearby Hemlock Overlook Regional Park and then recoup in the sunshine at this family-friendly vineyard. Small snacks are for sale, live music plays on Saturday afternoons and while tiny tots are not allowed on the back deck the outdoor space is perfect for picnics and play time. They also feature fun events like movie nights and yoga.

The relaxed family-friendly vibes are immediate when you head out to Sugar Loaf Mountain Vineyard in Dickerson, MD. A designated play area just for wee ones with an expansive space beyond encourages all the running, jumping and games of tag they can muster. No need to sneak in snacks you can buy small ones here or bring your own set of sweets and savories to munch on while you spend a whole day outside enjoying vino and familia.

Want to feel as if you are on a bit of a getaway? Port Potomac Vineyard and Winery is the place to find a bit of Tuscany in Northern Virginia. Take advantage of one of their family-friendly events held year-round like outdoor movie nights and live music. Reservations are required.

Just saying the name, Quattro Goombas is fun, so visiting is certain to be a treat. Wine, frozen sangria, craft beer, thick crusty pizza, tacos and beverage flights are all in a day’s visit. Bring a picnic and lounge around while the kiddos play; you can literally spend an entire day here without getting bored. There’s plenty of room to explore, vineyards to admire and of course – wine to drink! Don't forget to reserve your space before you go.

In addition to some of the yummiest pasture-raised meats, fruit and veggies, this working farm pours some of the tastiest wines near the DMV. Swing by Thursday-Sunday for sips and family-friendly self-guided tours. There's plenty of running around space for the littles and the rustic scenery makes for fabulous photo opps.

Located on the Monticello wine trail near Charlottesville, VA, Keswick’s 400-acre Edgewood Estate is the quintessential manor with breathtaking views of the countryside and the Blue Ridge Mountains. While it’s a gorgeous spot for a high-class wedding, you’ll feel equally at home with your little ones in tow for a wine tasting and tour. Crayons, coloring books and games are available to keep them busy while you swirl and swish the goods. Check their website for family-friendly events.

Enjoy live music every Sat. & Sun. at this Loudoun County brewery that serves up wine and cider along with their cold ones. Kids and pets are always welcome. Due to COVID, the playground is currently closed, but there is plenty of space to run, roam and tire out tiny legs.