Historic downtown Leesburg getaway Northern Virginia

Leesburg Getaway in Northern Virginia Wine Country

A Leesburg getaway in Northern Virginia wine country offers a wide range of dining and shopping experiences in a walkable downtown surrounded by pastoral scenery and historic sites. The town of Leesburg was founded in 1758, and the beautifully preserved downtown is a fun destination for enjoying local food, wine, and beer in casual to refined restaurants. Leesburg is also a perfect base for exploring Loudoun County’s many farms, wineries, and breweries.

Leesburg getaway in Northern Virginia wine country

Historic Leesburg Virginia

Things to Do on a Leesburg Getaway in Northern Virginia

Shop for Treasures in Historic Leesburg or Deals at the Outlet Mall

Black Shutter Antiques Leesburg VA

Black Shutter Antiques Leesburg VA

The streets of historic downtown Leesburg are lined with interesting antique shops, galleries, and small local stores perfect for a day of relaxed shopping. Browse the collection at Black Shutter Antiques and the Leesburg Antique Emporium. Check out the art at The Cooley Gallery and pick up a local souvenir at the Very Virginia shop. For discounts and deals, head to the Leesburg Corner Outlet Mall on the eastern side of route 15. We shop there frequently for hiking and outdoor clothing deals at Columbia.

Admire Architecture and History in Leesburg’s Downtown

County Courthouse gate Leesburg Virginia

Loudoun County Courthouse Leesburg Virginia

Leesburg Virginia has been the center of Loudoun County government for over 250 years, Visit the Loudoun County Court Square to learn about the “perfect sneering nest of rebels” the Union encountered when they entered Leesburg in 1862. From the Courthouse, walk the streets of the downtown area to see well preserved buildings and homes hugging the streets.

Hike Through History at Ball’s Bluff Battlefield Park

Cannon and cemetery wall Balls Bluff Battlefield

Cannon and cemetery wall Balls Bluff Battlefield, Leesburg VA

Leesburg’s position on the Potomac River was an important crossroads in the 1800s. The town changed hands 150 times during the Civil War. Learn about a decisive Confederate victory at the Battle of Balls Bluff, and visit one of the smallest National Cemeteries in the country, on a hike through the battlefield. Ball’s Bluff was the site of the first Civil War engagement to take place in Loudoun County. The park has an excellent interpretive trail that explains how the battle unfolded. Other trails include sometimes steep, wooded hikes to the Potomac River and a segment of the Potomac Heritage Trail.

Hike to a View at Red Rock Wilderness Overlook Regional Park

River view Red Rock Wilderness Overlook Park in Leesburg VA

River view Red Rock Wilderness Overlook Park in Leesburg VA

Enjoy a short hike to a bluff above the Potomac River at Red Rock Wilderness Overlook, a 67-acre park located at the eastern edge of Leesburg. The hike begins at the ruins of several buildings, built in the late 1800s by wealthy gentleman farmer Charles Paxton.  A 1.2 mile circuit trail takes you through the woods, down to the Potomac, and along a bluff with great river views.

Explore an Historic Virginia Farm at Morven Park

The manor house at Morven Park Leesburg VA

The manor house at Morven Park Leesburg VA

There is a lot to see on a visit to Morven Park. The estate includes 1000 acres of lawns, trails, equestrian and athletic fields; two museums; and an historic manor house. Tour the manor house to learn about Virginia Governor Westmoreland Davis. Davis and his wife Marguerite purchased Morven Park in 1903 and built it into a productive farm following his ideals of sustainable agriculture and civic leadership. Tours of the mansion and two museums—the Museum of Hounds & Hunting of North America, and the Winmill Carriage Museum—are available throughout the year except January. Allow extra time to explore the grounds or watch an equestrian event.

Stroll the Grounds at Oatlands

The grounds at Oatlands can be enjoyed on a self-guided walking tour. The property features impressive trees, a formally terraced garden with boxwood alleys, reflecting pool, herb garden, and other plantings. Interpretive signs give key information about the gardens and the nineteenth century architecture, including the second oldest greenhouse in the country. Tours of the Oatlands mansion are available hourly in season, and special events and tours are offered throughout the year.

Take a Scenic Drive and an Historic Ferry Across the Potomac

A Leesburg getaway would not be complete with a scenic drive through the lovely countryside of Loudoun County. We recommend this 30 mile scenic loop, which offers a chance to visit wineries, take a ride across the Potomac on the Jubal A. Early at White’s Ferry, and visit the hikes listed above. The ferry is a fun activity even if you just ride across to Maryland and back. Some of the winery roads are dirt or crushed stone, but they are all easy to navigate and offer relaxing views of the Virginia countryside.

Bike the Washington & Old Dominion Trail

The 45.5 mile long, paved Washington & Old Dominion Bike Trail passes directly trough the town of Leesburg. The section from Leesburg west to Purcellville is especially scenic. Bikers heading west from town encounter a 4 mile long gradual climb over Catoctin Mountain through Clark’s Gap on a winding and mostly shady trail. Stop in Purcellville for tasty barbecue and brews before your return trip to Leesburg.

Where to Stay on a Leesburg Getaway

Lansdowne Resort Leesburg VA

Lansdowne Resort Leesburg VA

Lansdowne Resort and Spa is an excellent base for a Leesburg getaway. The comfortable rooms were renovated in 2016. There are several restaurants, a spa, three golf courses, tennis, hiking, and plenty of comfortable spaces to relax between outings. The resort’s decor nods to the history of the 476 acre property. The location was an annual gathering place for the Algonquian Indians, and later became farmland owned by Lord Fairfax.

Lansdowne Resort grounds, Leesburg VA

Lansdowne Resort grounds, Leesburg VA

Guest rooms at Lansdowne Resort are roomy and comfortable. Request a higher floor for lovely views of the Lansdowne property and surrounding countryside. Golf lovers can play 45 holes on three different courses. Street and mountain bikes are available for exploring the roads and a segment of the Potomac Heritage Trail, which crosses the property. Spa lovers can choose treatments that feature leaves and wine from local Stone Tower Winery.

Comfy room Lansdowne Resort Leesburg VA

Comfy room Lansdowne Resort Leesburg VA

The Coton & Rye restaurant is named for the ancestral home of Thomas Lee, who managed the land for Lord Fairfax. The town of Leesburg is named after Thomas, not Robert E. or Thomas Lightfood Lee as many people think. Chef Marcus Repp partners with area businesses to procure local meats, produce, beer, and wine for the restaurant’s menu. We were not able to dine at the restaurant but look forward to a future visit.

Coton and Rye Lansdowne Resort Leesburg VA

Coton and Rye Lansdowne Resort Leesburg VA

Eat Like a Local on a Leesburg Virginia Getaway

Leesburg’s compact downtown offers a terrific range of tasty local dining choices, and there are several more great options a short drive away. Learn more in our full guide: 10 Tasty Leesburg Restaurants to Eat and Drink Local.


Shoes, Cup & Cork is a cool eatery on King Street. Stop by for a delicious breakfast in the main cafe  and be sure to order the biscuits. The restaurant also offers dinner in an upstairs speakeasy. In warm weather, slip through the narrow alley for a meal and a cocktail in the Secret Garden.

Shoe decor Shoes Cup and Cork Leesburg VA

Shoe decor at Shoes Cup & Cork Leesburg VA


Fireworks Pizza offers delicious housemade pizzas, salads, and daily specials. When the weather is nice, the long, wrap-around porch offers a mix of covered and sunny seating.

Fireworks Pizza porch Leesburg VA

Fireworks Pizza, Leesburg VA

Burger lovers head to Melt for gourmet cheeseburgers. Meats and toppings range from standards to more exotic and quirky choices.

Señor Ramon Tacqueria is a casual spot for tasty tacos. You can’t go wrong with the Señor Ramon taco, filled with carne asada, chorizo, grilled guacamole, sour cream, red onions and hot lava jelly.


King Street Oyster Bar serves delicious jumbo lump crab cakes, fresh shellfish, and a rich and creamy blue crab and corn chowder. The dinner vibe is relaxed, but the small space can get quite noisy during Happy Hour, when $5 drink and food specials draw a lively crowd.

King Street Oyster Bar happy hour Leesburg VA

King Street Oyster Bar happy hour Leesburg VA

Tuscarora Mill is popular for special events and family get togethers, and it’s a nice choice for a romantic meal. Tables are spread throughout several rooms in a beautifully restored mill. Dinner specials are always tempting, and the filet mignon is a favorite. Try to save room for the Warm Butterscotch Bread Pudding.

Another refined restaurant in an historic building, Lightfoot is a lovely spot for a special dinner or lunch. The restaurant is named after Declaration of Independence signer and local hero, Francis Lightfoot Lee. The restaurant occupies a bank building built in 1888, and the wine is stored in the original bank vault.

Lightfoot birthday dessert

Lightfoot birthday dessert


Stop by little Mom’s Apple Pie for handmade fresh pies, many filled with their own locally-grown fruit, plus cookies and other goodies. The pies are sold whole or packaged by the slice, perfect for Leesburg getaway road trippers.

Moms Apple Pie Leesburg Virginia

Moms Apple Pie Leesburg Virginia

Sample Leesburg Breweries on the LoCo Ale Trail

Crooked Run Brewing

Crooked Run Brewing Leesburg Virginia

Crooked Run Brewing Leesburg Virginia

This farmhouse nano-brewery creates tasty IPAs, sours, and fruit-infused beer in a small space in Market Station. Crooked Run has been a success since opening, and they have a second, larger location in nearby Ashburn.

Loudoun Brewing Company

Loudoun Brewing Co Leesburg VA

Loudoun Brewing Co Leesburg VA

A home away from home for locals, Loudoun Brewing has 5 or 6 home brews on tap and live music on the weekends. There is seating indoors and on a deck outside,

Dog Money serves a range of brews and a pub menu with salads, sandwiches and entrees.

Black Walnut Brewery is a downtown brewer with picnic table seating in a festive backyard.

Black Hoof Brewing is a family-owned brewery with a downtown location and a changing line-up of beers.

You’ll find both Vanish Farmhouse Brewery and Barnhouse Brewery north of Leesburg on Route 15.

Relax and Sip at a Loudoun County Winery

Loudoun County is the heart of Northern Virginia wine country, and there are plenty of wonderful places to relax and sip in the Leesburg area. Follow the scenic drive suggested above to visit Lost Creek and the patio in the trees at Tarara, or several others choices along this route.

Lost Creek Winery Leesburg

Lost Creek Winery Leesburg

To the west and south, we like the outdoor spaces and the  views at Casanel Vineyards, Stone Tower Winery, and Willowcroft Farm Vineyards. The oldest winery in Loudoun County, Willowcroft Farm sits atop Mt. Gilead. Outdoor picnic tables offer views of the distant Blue Ridge Mountains, or enjoy your wine in a historic red barn which predates the Civil War. Explore more Sensational Northern Virginia Winery Views Close to Washington DC.

Willowcroft Winery view

Willowcroft Winery view

Casanel has a nice back deck overlooking a small pond, and Stone Tower draws crowds to it’s open hilltop yard and tasting room. Driving the dirt road to Stone Tower, past open fields and farms, is part of the fun.

Stone Tower Winery view

Stone Tower Winery view

A Leesburg getaway in Loudoun County offers history buffs, foodies, craft brew and wine lovers, and outdoor adventure fans plenty to do and many reasons to return. Whether your Leesburg getaway is a weekend escape from the city, a local staycation, or a quick day trip, you’ll find plenty of fun places to explore, dine, and drink in Northern Virginia wine country.

You’ll find more Leesburg getaway and Northern Virginia fun in these related articles:

Follow Fun in Fairfax VA on FacebookTwitterPinterest, and Instagram for more fun things to do, places to visit, dining and drink, and special events in the Northern Virginia, Washington DC, and surrounding areas.

A Leesburg getaway in Northern Virginia wine country offers great dining and shopping in a walkable downtown surrounded by lovely scenery and historic sites.

This article was published in 2016 and updated in 2018.

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