Loudoun County, Virginia

• Book a room at the newest addition to Leesburg’s hospitality scene, Hotel Burg, which opens to guests in August.

• Visit one of the many wineries in the area—such as Breaux Vineyards in Purcellville or Good Spirit Farm Winery in Round Hill.

• Browse vintage furniture and home decor at Lucketts Store in Leesburg.

• Plan your trip to Loudoun County in the autumn, when the area’s fall foliage is on full display.

Virginia contains mountains, vineyards, small towns, luxury hotels, artistic hubs, and some of the most inspiring culinary scenes on the East Coast. While you could certainly traverse the Commonwealth to witness its multiplicity, you could also stick to one region—namely, Loudoun County.

Often referred to simply as “Loudoun,” Loudoun County is made up of a handful of towns and communities: Leesburg (the county seat), Middleburg, Purcellville, Waterford, Sterling, Round Hill, Lucketts, Hillsboro, Lovettsville, Hamilton, Ashburn, and Bluemont. “As a business owner in Loudoun, I really appreciate the diversity. Each city or town has its own vibe and culture. I also like how each city has its own local flair and events that the community can support,” says Silas Redd, owner of Nostalgia Boutique and Mister on Main in Purcellville.

“Some people ‘pit’ eastern Loudoun versus western Loudoun,” Jody Brady, founder and director of the Loudoun Appalachian Trail Festival, tells Travel + Leisure, explaining how eastern Loudoun is known for its suburban developments and shopping centers while western Loudoun has more farms and wineries. “But I think Loudoun works because east and west mix all this up and make the county the dynamic, thriving place it is,” she says. And as Reagan Walker, owner of Waterford Reservations, shares, “Whether you are into outdoor activities or culinary experiences, or you’re a wine or beer lover, there is truly something for everyone.”

Read on for our comprehensive guide to Loudoun County, Virginia.

Best Hotels

Hotel Burg

“Charming bed-and-breakfasts abound in Loudoun, and an array of hotels line the roads near Dulles International Airport, but the most recent talk of the town is the new, elegant Hotel Burg in the heart of Leesburg’s historic district,” says Brady. Set to open to guests this summer, the luxury boutique hotel will have a restaurant, The Huntōn, a cocktail bar, The Diana Lounge, and a rooftop bar.

Lansdowne Resort

“I have also loved visiting Lansdowne Resort. It is expansive, and the food is top-notch,” says Redd. The 500-acre, family-friendly property is located in Leesburg, and its amenities include three golf courses, a spa with 12 treatment rooms, and three outdoor pools.

Salamander Middleburg

“Of course, five-star Salamander Resort in Middleburg remains the top-tier stay in Loudoun,” says Brady. The resort is ideal for those travelers who enjoy balancing activities with relaxation. There’s horseback riding, golf, tennis, and a pool, plus a full-service spa to retreat to when you’re ready for some downtime.

Best Things to Do

Go for a hike.

It’s not hard to find a way to stay active in Loudoun County, and one of the best ways to get in your steps and see the area is to hike. “Walk a stretch of the Appalachian Trail and picnic at the Bears Den Overlook, or explore the trails at Sweet Run State Park, Virginia’s newest state park,” says Brady.

Find some live music.

“We have so many talented local musicians, and you can’t beat the free summer music series in Hillsboro and Leesburg,” says Brady, who also recommends listening to music at Monk’s BBQ or Wheatland Spring. “Tarara Summer Concert Series is another favorite during the summer and early fall,” says Walker, describing “one of the most beautiful concert venues” she’s been to. “Invite your friends and family and enjoy a variety of great bands throughout the season.”

Visit a local winery, brewery, cidery, or distillery.

Places to grab a locally made drink abound in Loudoun County. Redd prefers Walsh Family Wine—and recommends a glass of their viognier—and Catoctin Creek Distillery, “for one of their highly curated ‘Dinner at the Distillery’ events.” Walker suggests checking out Breaux Vineyards, where you’re “surrounded by exquisite views of the vineyard,” and 8 Chains North. The latter, she notes, is dog-friendly and a “sure spot to stop if bringing your pup along.” Brady also has a few favorite spots, including Black Hoof Brewing Co. in Leesburg and Henway Hard Cider in Bluemont.

“In addition, most wineries and breweries have live local music and great food options on the weekends. Keep an eye out on their event calendars as most places host special events—festivals, wine dinners, and more,” says Walker.

Attend a renowned tag sale.

Every year, thousands of shoppers make their way to Loudoun County to attend the Purcellville VA Tag Sale. “One of the largest events in Purcellville, this one-day event is a shopping and collectors’ dream! Our local boutiques have special discounts, and there are over 150 vendors selling antiques, handmade items, etc,” says Redd.

Towns to Visit

Purcellville

“Purcellville is probably my favorite. It feels like it is one of the last small towns in Loudoun that hasn’t been overdeveloped. The community is really supportive of the restaurants, boutiques, and events,” says Redd.

Leesburg

“Downtown Leesburg has become such a fun place over the years, with so many wonderful restaurants, historic sites, shops, and live music,” says Walker. “The town also celebrates First Friday; the downtown is buzzing with people enjoying live music, art exhibits, open storefronts, food, and drink.”

Round Hill, Hillsboro, and Bluemont

“Round Hill, Hillsboro, and Bluemont are Loudoun’s three ‘A.T. Communities,’ a designation each town earned from the Appalachian Trail Conservancy for their commitment to the protection and promotion of the Appalachian Trail,” says Brady. “These three communities work together to put on the annual Loudoun A.T. Festival in June with a full day of Americana music, trail talks, nature crafts, and an art show.”

Walker also adds that Hillsboro has an annual Independence Day celebration, which she describes as a “hometown experience full of life,” with “fireworks, live music, food, wine, beer, and kids’ fun.”

Waterford

“I might be biased because I grew up in the town and now live two miles outside of it, but there is something magical about Waterford,” says Walker. “It is filled with history, beautiful historic homes, and hosts the Waterford Fair annually. There is a lovely walking trail called the Phillips Farm Trail, which is a walk along the Catoctin Creek adjacent to the town.”

Middleburg

There’s no shortage of charm in Middleburg, a small town where equestrian heritage and storied history are on display around every corner. It’s also home to several luxe hotels and inns; along with Salamander Middleburg, there’s The Red Fox Inn & Tavern as well as Goodstone Inn & Restaurant.

Best Restaurants

Purcellville

“Magnolias at the Mill has always been a top choice of mine. Whether I’m celebrating a special occasion, meeting my girlfriends for brunch, or simply stopping in for a nice lunch or dinner, the experience is always top-notch,” says Walker. For what Redd calls the “best BLT sandwich ever,” head to Market Burger Fries & Shakes. If you want a “great home-cooked breakfast,” he suggests Purcellville Family Restaurant.

Leesburg

Walker calls EagleTree Farm Winery & Restaurants a “hidden gem.” “Located outside of Leesburg, they offer a delicious seasonal menu with excellent service,” she says. While in Leesburg, stop by any one of Brady’s favorites: Tuscarora Mill, SideBar, Shoe’s Cup and Cork, or The Conche.

Hillsboro

“I am a pizza lover, so one of my favorite stops is in the town of Hillsboro at Market in The Gap,” says Walker. She shares it “has amazing wood-fired pizza made right in front of you,” a “smaller cozy atmosphere inside,” and “an outdoor area for seating in warmer weather.”

Middleburg

If you find yourself in Middleburg, there are two iconic restaurants that come recommended by Brady. For the more traditional route, make a reservation at the Red Fox Inn & Tavern. In the mood for something more casual? King St. Oyster Bar, with its seafood entrees and happy hour specials, should do the trick.

Best Shopping

Leesburg

“I am very into design and decor, so I absolutely love going to the Lucketts Store. They have so many amazing finds. I could literally spend all day there and will always find something to take home,” says Walker. “Leesburg boutiques make for a wonderful afternoon of shopping, including Muz & Roz, wldwst, Misguided Angels, Birch Tree Bookstore, Brick & Mortar Mercantile, and Madisonbelle,” adds Brady.

Waterford

“I love The Corner Store in Waterford. Pop in and explore amazing vintage furniture and locally produced and handmade goods,” says Walker. “The store also has an excellent small menu created by Chef Estelle Richer-Legault. The freshness of the menu and experience are exceptional.”

Purcellville

“I like to score second-hand treasures in Purcellville at Nostalgia, Twigs, It’s Bazaar, and Re-Love It,” says Brady. Redd is also a fan of Twigs. “This place is the queen of unique gifts! Everything from jewelry and candles and soaps to tabletop books and womens wear,” he says, adding that Twin Flame Vintage, a “kitschy boutique focusing on vintage clothing, housewares, home decor, and ephemera,” is another one that travelers should have on their list. If it’s menswear you’re after, take a peek at Redd’s Mister on Main boutique housed inside its sibling store, Nostalgia.

Round Hill

“Elsass in Round Hill is one of my favorites,” says Redd. “It’s a former mechanic shop converted into an antique store specializing in French antiquities.” Elsass is open from Friday through Sunday or by appointment.

Lovettsville

According to Walker, the “best goat cheese around” can be found at Georges Mill Farm Artisan Cheese in Lovettsville. Long Stone Farm is also on her shortlist; bring a cooler so you can keep the pork, eggs, and other perishable products you pick up cold.

Best Time to Visit

“Fall is hands-down the best time to visit,” says Redd. “There’s nothing better than enjoying a local glass of wine and seeing the seasons change from the leaves on the trees and native plants.” Alternatively, says Brady, if you explore Loudoun in the spring, you may get to see the wildflowers at Balls Bluff or attend Loudoun Wildlife Conservancy’s Spring Native Plant Sale and the Leesburg Flower & Garden Festival in April. Walker, on the other hand, recommends planning your visit for late summer: “The backdrop is so beautiful this time of year. If you visit wineries, the vines are so lush and beautiful,” she says.

How to Get There

If you plan on flying to Loudoun, you’ll want to choose Dulles International Airport (IAD) as your destination. From there, you can either rent a car or book a taxi or rideshare service. IAD is only about a 20-to-40-minute drive away from Loudoun, depending on where you’re going within the county. There’s also the option to come by train from D.C. There are three Metrorail Silver Line stations that serve Loudoun: Dulles International Airport, Loudoun Gateway, and Ashburn Station.

How to Get Around

The most convenient way to explore Loudoun County is by car. This allows you the freedom to visit the different towns that make up the county, popping into different restaurants, shops, and wineries. Just be sure to assign a designated driver ahead of time if you plan on indulging in any wine or other alcoholic beverages.

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