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Step Back In Time in Historic Loudoun County, VA: D.C.’s Wine Country

Nestled in the Blue Ridge Mountains of Virginia, Loudoun County is known for its many award-winning wineries. Located close to the bustle of Washington, D.C., the small towns of Loudoun County will make you forget that the city even exists. Step back in time to historic towns, gorgeous views, and great wine and craft beer. 

Lodging in Loudoun County

Hummingbird Treehouse
Loudoun County VA
Hummingbird Treehouse

Your priority is securing lodging. Head straight to Waterford Reservations. I stayed in the Hummingbird Treehouse, but owners Donnie and Reagan Walker have a variety of accommodations to suit you and, if needed, your pet. Donnie’s experience as a general contractor with an affinity for preservation and restoration shines through. Reagan’s hand in the interior design leaves the accommodations lovely and cozy. They are a great pair to ask for local recommendations, as they grew up in the area. 

Loudoun County Eats and Drinks

"Mighty Fine Virginia Wine" mural
Loudoun County

Willowcraft Farm Vineyards produced the first wine in Loudoun. Forty years later, there are over 50 wineries in the area. If wine is not your thing – I call myself a “baby” wine drinker – there are over 30 breweries available to slake your thirst. Six Cider Houses. Over 20 independent coffee houses. Three distilleries. You will never be thirsty in Loudoun. 

Here are some places that helped me experience the area’s flavors. 

Market in the Gap 

Charles Town Pike, Hillsboro

Pizza from Market in the Gap

Donnie and Reagan of Waterford Reservations gave me a grand welcome to Waterford on my first night by taking me to some great local places. Market in the Gap is a small building just off the road; it would be easy to take little notice of it.  That would be a mistake. The owner is Andy of Andy’s Pizza in Leesburg and Lovettsville. This location offers wood-fired pizza along with a small market area. The building only holds 2-3 tables, but seating is available outside. The pizza was phenomenal, made even better by Andy’s company. They are closed on Sunday and Monday, so plan to visit the other days of the week. 

Bear Chase Brewing Company

33665 Bear Chase Lane, Bluemont

Bear Chase Brewery cup with a view of the Blue Ridge Mountains.

If you want gorgeous views and a laid-back atmosphere, head to Bear Chase Brewing. The back side of the restaurant holds a covered seating area offering stunning mountain views. On the expansive lawn are dozens of Adirondack chairs clustered for group seating. I was told it’s an excellent place for families to hang out – the parents chat while the kids run around and play. Everybody wins! With live music from Thursday through Sunday, Bear Chase Brewing deserves a visit. 

King Street Coffee

110 S. King St., Leesburg

The city of Leesburg has a lovely historic downtown area perfect for strolling. I started my day with a French vanilla rose latte from King Street Coffee. I love trying new flavors and have a weakness for the floral ones. This brew didn’t disappoint, nor did the friendly service. 

Fabbioli Cellars 

15669 Limestone School Rd., Leesburg

I’m a novice wine drinker, so I wasn’t sure I would enjoy visiting wineries. I’m not very knowledgeable about the different kinds, and some people take it so seriously. Still, Fabbioli Cellars is determined to make wine fun again. The tasting room is striking, with a beautiful tree sculpture in the middle. I toured the extensive vineyards with co-owner Doug Fabbioli, who stressed cooperation over competition in the Loudoun County wine community. In addition to sharing his expertise, he also shares his land. Two community groups have a garden plot on site.

Taylor Swift Eras display
Fabbioli Cellars

There’s a different theme to their monthly tastings, and I happened to be there during Taylor Swift month! Their on-site food scientist said she had to dig deep to develop that month’s pairings and knocked it out of the park! Pairings included foods related to Swift, such as drumstick squashies that she referred to as “legit candy” and a Cinnamon Toast Crunch bar, allegedly one of Swift’s favorite late-night snacks. 

Tuscarora Mill 

203 Harrison St., Leesburg

Step inside a 19th-century grain mill for your memorable dinner at Tuskies, as the locals call it. While the menu reflects the restaurant’s fine dining aspect, the atmosphere and wait staff are casual. My friends and I shared the fried green tomatoes as an appetizer, and I devoured the shrimp and grits for my entree. It was busy on a weeknight, so you may want to make reservations if you plan to eat here. 

Walsh Family Wine

16031 Hillsboro Rd., Purcellville, VA

Inside of Walsh Family Wine in Loudoun County VA

Loudon County is doing its best to abolish snobbery around wineries, and Walsh Family Wine is a prime example. The primary public space is open, with comfortable seating grouped to encourage conversation. The atmosphere is laid back as if you were in someone’s living room. Special events show the community in the wine industry. Their “Bar Takeover” event invites other beverage producers to host a tasting in their space and talk about their varieties. 

Bia Kitchen

108 N. 21st St. Purcellville 

The Europen-style eatery Bia Kitchen delivers an atmosphere reminiscent of an Irish pub. The interior features were all custom-crafted in Drogheda, Ireland, giving off a cozy but elegant vibe. My lunch partner and I had the delicious PEI Mussels for an appetizer while I ordered the Slow Roasted Brisket Au Jus for my entree. The portion size and the flavorful brisket were excellent. 

LoCo Ale Trail 

If you are a craft beer and cider drinker, check out the LoCo Ale Trail! Print a passport or pick one up at your first brewery. The beverage stops are grouped into area clusters, or you can choose one of the categories, such as “Brews With Views.” Collect prizes after visiting; there is no time limit, so repeat visitors can also have fun with this. 

Things To Do in Loudoun County, Virginia

Immerse Yourself in History in Waterford, VA

View of Waterford Mill and historic marker
Loudoun County

Waterford is my favorite area in Loudon County. The town of Waterford is a National Historic Landmark founded in 1733. There are 97 homes in town, and 64% were built before 1861. Many of them date to before 1840. As a history lover fond of colonial American history, this area hit all the right notes with me. It has a unique Civil War history as well. While the state of Virginia seceded from the Union, Loudoun County had Union sympathies and organized the independent Loudon Virginia Rangers, the only organized group of soldiers from Virginia aligned with the Union. 

I have another reason to love Waterford (aside from the treehouse accommodations). It has been home to three Pulitzer authors: Larry McMurtry (Lonesome Dove), Geraldine Brooks (March), and my favorite, Tony Horwitz (prize for National Reporting). Another resident, playwright John Guare, was a finalist for the Pulitzer Prize for Drama for Six Degrees of Separation.

Loudon County Shopping

The historic downtown area of Leesburg is perfect for strolling, browsing, and shopping. I have to look for a bookstore wherever I visit, and Birch Tree Bookstore is a unique stop. As I walked into the shop, the owner’s dog greeted me, which is always a good sign. As I ventured further, I saw it was a combo bookstore and plant store! At Very Virginia, I was able to pick up some souvenirs and discuss Virginia peanuts vs Georgia peanuts with the staff! There are hobby stores, clothing stores, and more. Pro tip: there are several parking decks available in the area. I didn’t pay attention to the deck’s name, and the address wasn’t on the ticket. I wandered briefly before retracing my steps back to my first stop! 

The Marshall House at Dodona Manor Park

East Market St., Leesburg

Living Room in Dodona Manor
Loudoun County

George C. Marshall may not be a name you immediately recognize, but it should be. General Marshall was vital to an Allied win in World War II, and his Marshall Plan was instrumental in helping Europe recover economically after the war. Despite his fame and stature, Marshall and his family lived in a decidedly down-to-earth manner. His 19th-century home is open for 75-minute tours Friday through Sunday. If you visit during the week, there are two self-guided exterior tours of the architecture and trees on the property. When visiting, park in the back of the shopping center next door at 312 East Market St. A path leads you through the garden to the house.

Luckett’s Store 

42350 Lucketts Road, Leesburg 

Elephant Slide outside Luckett's Store
Loudoun County

You guys, Luckett’s Store is right up my alley. It’s a vintage, antiques and home furnishings store with a large assortment of items inside and outside. Allow plenty of time for a productive shopping trip! The building was a general store built in 1879 and restored in 1996. Maybe bring the mini-van or truck for this trip. 

Red Rock Wilderness Overlook Regional Park 

43098 Edwards Ferry Rd., Leesburg 

Image of the Potomac River through trees
Loudoun County

This site is a 67-acre park on the banks of the Potomac River. Remnants of historic buildings are on site with interpretive signs. The trail is rustic, but the views of the Potomac River and this peaceful spot are worth it. Trails are blazed with colorful marks, but there is little signage along the trail. As a solo female, I proceeded cautiously since the trail was remote. This would be best experienced with a friend or two. 

Lawless Forge

22611 Markey Ct., Unit 106, Sterling 

Blacksmith shaping a metal rod

Closer to Washington, D.C., is an increasingly hot activity, pun intended. Sign up for blacksmithing classes at Lawless Forge! While I didn’t have time for one of their three-hour classes, Blacksmith Zander Shaw gave me a demonstration. Participants can choose between crafting a bottle opener, horseshoe knife, BBQ Fork, chopsticks,  or a flower bouquet!  Ages six and up are welcome; Lawless Forge advises that most children 11 or 12 can complete projects with minimal assistance. Ages 15 and younger require an accompanying adult. If you’ve attended one of their classes in the past, you’re welcome to their open shop sessions. Remember that many items you can make might not be allowed in carry-on luggage! 

Outside the City, But An Entire World Away

Vineyard under blue sky

Please trust me when I say this is one of the most beautiful and peaceful areas I’ve visited. I was unsure I would enjoy a destination promoted primarily for its wineries, but there is so much more to Loudoun County than that. As a history and genealogy librarian, I applaud the attitude of preservation and celebration surrounding the area’s history. Loudoun County can also deliver if you enjoy wide open spaces and scenic views. The Blue Ridge Mountains are a fantastic backdrop to the expansive farmlands and quaint historic neighborhoods. A visit to Loudoun County, VA, is convenient from Washington, D.C., but it will feel a world away.

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