Dog-Friendly Activities in Upperville, VA

Three Fox Vineyards is a dog-friendly winery in Delaplane, VA. Fido is welcome inside their tasting room, except for the upstairs lounge, and water and dog treats are available. Here you will find fantastic and affordable tours, tastings and pairings. Their four season deck provides the north and west views of the property overlooking Crooked Run Creek and the rolling hills.

8 Chains North is a dog-friendly boutique farm winery showcasing handcrafted, Old-World-style wines in Waterford, VA. Their philosophy: Great wines are made in the vineyard. The warm and inviting tasting room has stunning vineyard views. Dogs are welcome inside and outside at the winery, and there's even a fenced off-leash area for your dog to run and frolic with other friendly canines! Open year-round, the winery offers an extensive patio during the season, and a roaring fireplace in the cold-weather months. Their friendly and knowledgeable staff looks forward to making your visit a truly memorable one.

Barrel Oak Winery & Brewery is a beautiful family-owned winery in Delaplane, VA, that welcomes dogs with open arms. They say that Barrel Oaks Winery stands for "BOW" (as in bow wow), and they even have wines named after their dogs! It is a great place to tour the countryside with your dog, or sit on their pet-friendly patio and enjoy wine and cheese while making new friends.

Pet-friendly Chrysalis Vineyards welcomes leashed dogs to explore the grounds with you and enjoy a seat on their outdoor patio in Middleburg, VA. Take in the scenic views while sipping on a glass of wine. You can also enjoy a light bite of hummus and crackers, paninis, or pizza from Little River Bakehouse on site. Please leash and clean up after your pets during your visit.

Breaux Vineyards is a 404-acre winery and estate with stunning mountain views in Purcellville, VA. This pet-friendly vineyard offers wines harvested from 17 varieties of grapes. Leashed dogs are welcome in the spacious outdoor seating areas overlooking the vineyards, at Dog Days at Breaux, and in the Old Tasting room (Vin97). Dogs are prohibited from the Orleans patio, which is reserved for 21+ visitors without dogs.

Old Bust Head Brewing Company is an independent, solar-powered microbrewery in Warrenton, VA brewing traditional ales and lagers. Dogs are welcome to join you at outdoor tables on the covered patio between the taproom and production area. Rotating food trucks are often available.

Located on a hilltop on the edge of town, Mt. Defiance Cider Barn is the great place to spend an afternoon with Fido. Settle into a rocking chair by the fireplace on cold winter days, or sit out on the porch and enjoy the warm breezes. Well-behaved dogs are welcome in the tasting room. Snacks are available (cheese, crackers, and nuts) and on warm weather weekends food trucks are often available. The Cider Barn is closed on Mondays.

Perched atop scenic Hogback Mountain, Stone Tower Winery consists of 306 acres of rolling vineyards in Leesburg, VA. The dog-friendly Harvest Barn tasting room offers visitors plenty of space both inside and outside to sample chardonnay, pinot noir, and sauvignon blanc, among others. All group tastings and tours must be scheduled. Call for details and hours.

Vint Hill Dog Park is a fully-fenced park with plenty of room for dogs of all sizes to run and play in Warrenton, VA. This 1.25-acre park features benches, shade trees, a shelter, activity equipment, a water station and parking. Clean-up bags are often in stock at the waste stations in the park.

Leashed dogs are welcome at the State Arboretum of Virginia in Boyce. There are several pet-friendly trails, two small lakes, beautiful meadows, a picnic area, and open areas to explore. The attraction is just off Route 50, West of Washington, past Middleburg.

Great Country Farms in Bluemont, VA is dog friendly. Leashed pets are welcome to join you at the farm to pick-your-own fruits and vegetables or partake in other seasonal events.

The Warrenton Branch Greenway is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Warrenton! The map below shows a parking area with convenient access to the Warrenton Branch Greenway. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com.

Leashed dogs are welcome on the pet-friendly Raven Rocks Trail in Bluemont, VA. This challenging 5.7-mile out-and-back hike features an elevation gain of 1,535 feet with some steep climbs, but the magnificent view at the top makes it all worthwhile. The trail is accessible from April until October.

Sky Meadows State Park is a pet-friendly recreation area in Delaplane, VA. The 1,862-acre park features 10.5 miles of bridle trails, 22 miles of hiking trails, 9 miles of bike trails, and access to the Appalachian Trai. Bring Fido and the family along for an afternoon of hiking or picnicking outdoors while taking in the beautiful views.

Valley View Farm is a dog-friendly place in Delaplane, VA. Your leashed pup can join you at this fruit farm which offers craft beverages, a pick-your-own orchard, and a farm market, among other activities. Hours may vary depending on the season.

Take Fido to the dog-friendly Broken Window Brewing Company in Winchester, VA. Leashed dogs are allowed inside the taproom and on their heated outdoor patio. Browse their beer menu, which features signature concoctions such as the So It's Come To This, Mischief Managed, Mike The Red, Sometime Next Week and Lucky 13.

Leashed dogs are welcome to join you at an outdoor table at the pet-friendly winery, Walsh Family Wine, in Purcellville, VA. Enjoy a variety of wines by the glass or in a tasting with your furry friend by your side. You can bring your own food to enjoy a picnic outside or they also serve light bites.

Bring Fido to the pet-friendly Great Mane Brewery in Haymarket, VA. Leashed furry friends are welcome inside or at outdoor tables on their spacious patio, where water bowls will be provided. Stop by and check out their selection of delicious craft beers on tap.

The Washington and Old Dominion Railroad Regional Park (W&OD) is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Purcellville! The map below shows a parking area with convenient access to the Washington and Old Dominion Railroad Regional Park (W&OD). Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com.

Greenhill Winery & Vineyards is a dog-friendly, boutique winery in Middleburg, VA, delivering quality wine, with friendly and professional staff in a breathtaking vineyard setting. Leashed dogs are welcome on their outdoor patio. In addition to enjoying their local Virginia wines, they also offer Charolais beef and honey from their apiaries.