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    Dog Friendly Activities in Upperville, VA

    There are 43 dog friendly activities within 20 miles of Upperville. Use the links below to get an overview of each one, see pictures, print directions, and even read reviews from other dog owners. Coming from out of town? Get a discounted rate on pet friendly hotels in Upperville.

    Pet Friendly Three Fox Vineyards

    Three Fox Vineyards

    Delaplane, VA
    Three Fox Vineyards 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. See Details
    Pet Friendly Barrel Oak Winery & Brewery

    Barrel Oak Winery & Brewery

    Delaplane, VA
    Barrel Oak Winery & Brewery 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. See Details

    8 Chains North Winery

    Waterford, VA
    8 Chains North Winery 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. See Details

    Old Bust Head Brewing Company

    Warrenton, VA
    Old Bust Head Brewing Company 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. See Details

    Aspen Dale Winery at the Barn

    Delaplane, VA
    Aspen Dale Winery at the Barn Aspen Dale Winery at the Barn is a dog-friendly winery in Delaplane, VA. They produce award-winning wines on a working farm, complete with horses, goats, and chickens, and surrounded by fields, wetlands, and fish ponds. Leashed dogs are welcome on the property. Call ahead for seasonal hours. See Details

    Mt. Defiance Cider Barn

    Middleburg, VA
    Mt. Defiance Cider Barn 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. See Details

    Warrenton Branch Greenway

    Warrenton, VA
    Warrenton Branch Greenway 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. See Details

    Raven Rocks Trail

    Bluemont, VA
    Raven Rocks Trail 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. See Details

    Chrysalis Vineyards

    Middleburg, VA
    Chrysalis Vineyards 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. See Details

    State Arboretum of Virginia

    Boyce, VA
    State Arboretum of Virginia 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. See Details

    Breaux Vineyards

    Purcellville, VA
    Breaux Vineyards 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, and at Dog Days at Breaux — an annual celebration featuring live music, food and dog vendors. See Details

    Sky Meadows State Park

    Delaplane, VA
    Sky Meadows State Park 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. See Details

    Broken Window Brewing Company

    Winchester, VA
    Broken Window Brewing Company 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. See Details

    Stone Tower Winery

    Leesburg, VA
    Stone Tower Winery 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. See Details

    Vint Hill Dog Park

    Warrenton, VA
    Vint Hill Dog Park 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. See Details

    Washington and Old Dominion Railroad Regional Park (W&OD)

    Purcellville, VA
    Washington and Old Dominion Railroad Regional Park (W&OD) 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. See Details

    Rockland Park

    Front Royal, VA
    Rockland Park Rockland Park is pet-friendly. Formerly known as the Fishnet Property, this 219-acre park includes walking trails, a large playground structure, an 18-hole disc golf course, two large picnic shelters, outdoor fitness equipment, and parking areas. Leashed dogs are welcome on the trails, as long as they are cleaned up after. The park is open every day of the week from 7am to 8pm. See Details

    Valley View Farm

    Delaplane, VA
    Valley View Farm 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. See Details

    The Appalachian Trail

    Markham, VA
    The Appalachian Trail The Appalachian Trail is a pet-friendly hike in Markham, VA. Although the address we've listed is in Virginia, you can access the trail from numerous spots along the way. The path leads from Springer Mountain in Georgia to Mount Katahdin in Maine, totaling 2,181 miles. Dogs are prohibited from the following sections of the AT: The Great Smoky Mountains National Park, Bear Mountain State Park Trailside Museum, and Zoo and Baxter State Park. See Details

    Dividing Creek Beer Co

    Winchester, VA
    Dividing Creek Beer Co Take your pup to the pet-friendly Dividing Creek Beer Co, a nano brewery in the heart of Old Town Winchester, VA. Leashed and well-behaved dogs are welcome to join you inside the taproom or outside on their patio. Sit back and relax with a Big Tree Fall Hard seltzer, Weathered Hand Mexican lager, Dazzle Day Wheat Sour or Northern Neck ginger beer. See Details
    Upperville, VA, US