These casual places are ideal for parents to sip and kids (and dogs!) to run free—just not in the tasting room, please.
1st stop: Walsh Family Wine
Nate Walsh, owner of Walsh Family Wine, with his wife, Sarah, is a dad first, winemaker second. His toddler daughter, June, is as welcome as any 21-plus guest, and that’s the vibe he was looking to create when they opened the winery in the former North Gate Vineyards location in Purcellvile.
The tasting room has a living-room feel, with cozy furniture and plenty of space to move around. The winery also features a large, open patio looking out on the estate grapes, where pets and kids can roam. “I wanted to create an inviting, family-friendly space where everyone is greeted when they enter,” says Walsh. True to the community effort, the tasting room hosts local chefs and serves other regional wineries’ bottles and, instead of live music, the Walshes encourage guests to bring their own vinyl to play on the winery’s record player.
Next stop: 14 minutes; 9.8 miles

Bring home the bottle
Walsh Family Wine Bethany Ridge Sauvignon Blanc 2017 ($26)
Notes: “A bright, floral, vibrant expression of Bethany Ridge Vineyard [with] pronounced notes of grapefruit, lemon zest and orange blossom with a nice, textured mid-palate.”
Grape: 100% sauvignon blanc
2nd stop: Lunch at Vino9Market
Head over to Paeonian Springs for barbecue on the patio at Vino9Market, and you may be surprised to find butter chicken alongside the ribs and pulled pork. The restaurant and market’s new owners added a few Northern Indian favorites, including paneer and lamb biriyani, to the weekend menu. Little guests will love the mac and cheese, hot dogs and peanut butter and honey sandwiches while sitting on the outside patio, where no one cares if you’re a little loud.
Next stop: 7 minutes; 4.2 miles

3rd stop: Wine Reserve at Waterford
Down Route 9, the enormous, flat lawn at the Wine Reserve at Waterford is a perfect space to bring a ball, a kite and a picnic lunch—and enjoy a fun afternoon with a great bottle and the family. Leashes are required for four-legged friends. Older kids will enjoy fall activities, including food trucks and movies in the vineyard, while adults can volunteer their time at harvest in exchange for liquid rewards.
Cori and Jonathan Phillips opened the Wine Reserve in early 2017 in the former Loudoun Valley Vineyard location and marked their first harvest from the Waterford estate later that year. The pair works with Loudoun County’s wine godfather, Doug Fabbioli, to produce their estate wines. This fall, find Smitten Petit Manseng 2018. It also features other winemakers’ bottles a seasonal tasting menu, including Bluemont’s October One Vineyard, led by veteran winemaker Bob Rupy.
Next stop: 1 hour, 11 minutes; 42.9 miles

Bring home the bottle
Wine Reserve at Waterford The Leap Cabernet Franc 2017 ($31)
Notes: “Take a leap of faith into this jammy but pepper-filled first release of our Cab Franc vines.”
Grape: 100% cabernet franc
4th stop: Biking on the Washington & Old Dominion Railroad Trail
Bring your bikes and spend some time on the Washington & Old Dominion Railroad Trail as the 45-mile asphalt path winds toward its end in Purcellville. There are two public parking areas to access the W&OD in town and there are several playgrounds right off the trail.
Next stop: 47 minutes; 26.7 miles
5th stop: Grab a slice and pint at Fire Works Pizza
Everyone loves pizza, even diners who are gluten-free—if the crust is good. And it’s excellent at Fire Works Pizza in Leesburg, which offers more than two dozen pies, as well as mac and cheese, provolone-stuffed pepperoni rolls and a chocolate chip cookie sundae that will make everyone at the table cheer. The drinks focus is more on beers here, with a number of local selections, as well as gluten-free ciders and brews.
MORE …
Village Winery in Waterford offers free tastings of its unique fruit wines as well as non-alcoholic products made with its estate-grown elderberries … Stop for some bowling, cornhole and arcade games at Bowlero in Leesburg, or if the kids really need to blow off steam, hit up Atomic Trampoline Fun Center, which features foam pits, a dodgeball court and over 40 interconnecting trampolines, also in Leesburg.
Details
Walsh Family Wine: 16031 Hillsboro Road, Purcellville
Vino9Market: 40602 Charles Town Pike, Paeonian Springs
Wine Reserve at Waterford: 38516 Charles Town Pike, Waterford
Washington & Old Dominion Railroad Trail: Access points from Sherndon to Arlington County
Fire Works Pizza: 201 Harrison St. SE, Leesburg
This post originally appeared in our October 2019 cover story. To get more food & drink news straight to your inbox, subscribe to our weekly e-newsletter.