Dog Friendly Activities in Middleburg, VA

There are 3 dog friendly activities in Middleburg, and 36 more nearby. 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 Middleburg.

Pet Friendly Mt. Defiance Cider Barn
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
Pet Friendly Chrysalis Vineyards
Chrysalis Vineyards One of the finest estate wineries on the East Coast, Chrysalis Vineyards welcomes leashed dogs and has patio seating and grills for cooking. See Details
Greenhill Winery & Vineyards Greenhill Winery & Vineyards is a dog-friendly, boutique winery in Middleburg, Virginia, delivering quality wine, with friendly and professional staff in a breathtaking farm winery setting. They celebrate the terroir with 100% Virginia wines, and offer Charolais beef and honey from their apiaries. See Details
Three Fox Vineyards Three Fox Vineyards is a dog-friendly winery in Delaplane, VA. Fido is welcome to their tasting room and vineyard, and will even be offered water and treats. 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
Barrel Oak Winery & Farm Taphouse Barrel Oak Winery & Farm Taphouse 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 wines and cheeses while making new friends. See Details
8 Chains North Winery Just 8 miles west of Leesburg, in Northern Virginia, 8 Chains North is a dogs-friendly boutique farm winery showcasing handcrafted, Old-World-style wines. Their philosophy: Great wines are made in the vineyard. The warm and inviting Tasting Room and private event space have stunning vineyard views. Dogs are welcome inside and outside at the winery -- there is even a separate, 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
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
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
Cub Run Stream Valley Park A 800 acre mostly a wooded flood plain and mostly paved. It is approximately 5 miles. A very quiet park. Dogs can dip in the creek. There is plenty of shade when walking. See Details
Merrifield Garden Center Dog Park Very dog friendly Garden Center! They have a smallish dog park in their parking lot on the right side that is covered in mulch. It used to have separate sides for large and small dogs, but it seems they just took out the fence in between as well as made it longer and made it one big one. They've done a good job improving it though, now it reaches a tree and they added big bushes and picnic tables.

There's a mailbox with grocery bags where you can pick up poop. They also have dog bowls there, and if people keep them facing upwards then they catch rain water so that's nice. There's always tennis balls in there which is really nice, though some have chunks missing out of them and sometimes they're covered in poop.

The fence is a little less then pristine, but it works and overall we come here a lot. The actual people haven't been friendly though. Usually whenever we go there people pick up their dogs and leave, so that actually really sucks because then we have no one to play with.
See Details
Manassas National Battlefield Park 5,073 acres, dog friendly

Manassas National Battlefield Park, located north of Manassas, in Prince William County, Virginia, preserves the site of two major American Civil War battles: the First Battle of Bull Run on July 21, 1861, and the Second Battle of Bull Run which was fought between August 28 and August 30, 1862 (also known as the First Battle of Manassas and the Second Battle of Manassas, respectively). The peaceful Virginia countryside bore witness to clashes between the armies of the North (Union) and the South (Confederacy), and it was there that Confederate General Thomas J. Jackson acquired his nickname "Stonewall." Today the National Battlefield Park provides the opportunity for visitors to explore the historic terrain where men fought and died more than a century ago. More than 900,000 people visit the battlefield each year.
See Details
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 Leashed dogs are welcome on this 5.8 mile moderate hiking trail. Prepare for some steep climbs, but the magnificent view at the top makes it all worthwhile. Accessible from April until October. See Details
Stone Tower Winery Perched atop scenic Hogback Mountain, Stone Tower Winery consists of 306 acres of rolling vineyards, where delicate grapes are tenderly harvested to form an impressive array of world class artisanal wines. 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
Rock Hill District Dog Park This popular off-leash dog park is fully fenced with a separate small dog area. Be sure to bring water for your pet. See Details
Vint Hill Dog Park Vinton Hill Dog Park is a fully-fenced park with plenty of room for dogs of all sizes to run and play. There are no water facilities at the park. Clean up bags are often in stock at the waste stations in the park. There are benches for humans and some shade trees. See Details
Manassas Park Dog Park Located behind the Manassas Park Community Center, the Manassas Park Dog Park currently has two areas for dogs to play in off-leash. There is a spigot for drinking and filling pools. To enter the parking lot, come in from either Courtney Street or Tremont Street. Events occur throughout the year, highlighted by BREW's Beaglefest twice a year. See Details
Washington and Old Dominion Railroad Regional Park The Washington and Old Dominion Railroad Regional Park 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. 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
Creek's Edge Winery Creek’s Edge Winery located in historic Taylorstown, Virginia sits along the lovely Catoctin Creek in Northern Virginia’s Loudoun County. Sample an array of award-winning wines. Try traditional and seasonal food menu items, including charcuterie, salads, and sandwiches. Leashed dogs are permitted in outdoor areas. See Details
Seven Oaks Lavender Farm Seven Oaks Lavender Farm is pet-friendly. Visit the lavender shop with your pooch to see their floral items, which number 50 different lavender products that are made on the farm or nearby. See hours for when on-leash dogs are welcome. Seven Oaks is open to the public for lavender picking in June and early July. See Details
Bull Run Regional Park Bull Run Regional Park is pet-friendly. Spanning 1,500 acres, this park contains lots of pet-friendly trails for you to explore with your pooch. Stop along the way for a picnic with a view and check out the wildflowers on the Bluebell Trail. Dogs are welcome, as long as all mess is cleaned up after them and they remain on a leash. See Details
Dynasty Brewing Company Dynasty Brewing Company is pet-friendly. Located near One Loudoun and the W&OD Trail at Smiths Switch, this brewery, named for the first five presidents who hailed from Virginia, is a popular haunt for beer lovers. Leashed dogs are welcome at Dynasty, where they offer ten different brews on tap and rotate regularly with refreshing ideas from the brewery team. Hungry hounds can sink their teeth into a delicious bite from one of the many visiting food trucks to the brewery. See Details
Burnside Farms Burnside Farms is pet-friendly. Dogs are welcome to help their owners pick a lovely sunflower selection from the pet-friendly tracks and trails on the property. They also host a bunch of other fun activities to make a full day out for the family. See Details
BadWolf Brewing Company BadWolf Brewing Company is pet-friendly. Bring your pooch along to join you at this friendly brewery with board games and a chill atmosphere. They might even treat your pooch to a snack from behind the counter. Well-behaved, leashed dogs allowed inside and outside. They are open Wednesday to Thursday from 4pm to 10pm, Friday from 3pm to 10pm, Saturday from 1pm to 10pm and Sunday from 1pm to 5pm. See Details