The Perfect American City For A Romantic Getaway

Take in trails, art and 250th-inspired experiences  

Courtesy Kate Thompson/Town of Leesburg

The town has greenspaces for relaxing strolls and picnics like the small, serene 3-acre Raflo Park with a creek, picturesque bridge and a rotating sculpture display. Raflo’s sculpture exhibit is part of Leesburg’s free, self-guided walking art tour: Resembling an open-air gallery, the walking tour has an app for your phone to help you explore over 20 art pieces across town. 

My husband and I love cycling together, and the Washington and Old Dominion Trail is perfect for leisurely rides. Rent an e-bike from a number of outfitters in town to explore some of the 45-mile trail which is dubbed “Virginia’s skinniest park.” Paved and flat, the trail winds you through wooded areas, open fields and farms and vineyards views.

Steeped in history but with fewer crowds than DC, Leesburg is also savvy choice for celebrating America’s 250th anniversary. The ongoing, self-guided Lafayette in Leesburg walking tour is apropos, telling about the Revolutionary War hero’s 1825 visit. Adding context to the broader historical arc, the Loudoun Heritage Pass — released for the banner year — is a multi-site package covering five historic sites, many of which are in Leesburg. The pass notably includes the grand Leesburg manor home of the Marshall Plan’s architect, General George C. Marshall.

Courtesy Town of Leesburg

Sip and chat over craft cocktails and wine bars 

Trendy bars in old, intimate settings really heighten the mood factor. I find they’re extra vibe-y and romantic — a great place for a fun drinks date with your partner.

Tarbender’s Lounge is a 1920’s-inspired speakeasy in a centuries-old building. On the second floor of one of King Street’s old buildings, expect a sophisticated experience with soft lighting at Night Shift Cocktails. Order the Dealer’s Choice, a tailor-made cocktail with your favorite spirits and flavor profile. 

Step off the main drag and head nearby to Wine Bar Gvino in a 19th-century building. It’s a low-lit, sensory-rich spot exuding a European-cafe aesthetic. One of the owners is an illustrious sommelier from Lake Como — formerly of Cáfe Milano in DC. For tastes of the local wine without leaving town, visit October One Vineyard Wine Bar where you can sip estate wines. 

Tuck into exceptional fare 

Possessing a generous array of atmospheric dining options, the town has something for every taste — from small and cozy to modern and cool. One stand-out option for a special night out is the just-opened Shutters on King Street, occupying a historic structure which used to be an antique store. Fireplaces, warm lighting and exposed brick walls naturally stoke romance. The 3-floor upmarket restaurant is farm-to-table with a lively bar and restaurant, a rooftop patio and wine cellar. 

The more casual American brasserie, Shoe’s Cup & Cork is great for elevated burgers and sandwiches. Tucked away out back is their “Secret Garden” — an enchanting spot where you can play bocce ball while you tipple.

Romantic stays at a splurge-worthy boutique or wine country cottage 

For a true luxury experience befitting a milestone anniversary or birthday, book the new, 39-room Hotel Burg on King Street just steps from shops and restaurants. It’s a head-turner, with decor channeling Ralph Lauren across three buildings in Federal, Colonial and Italianate architecture. On the property is The Diana Lounge, an all-day cafe, a rooftop bar and The Huntōn, an upscale restaurant with open-fire cooking helmed by a chef with Michelin-star experience. 

The Airbnb cottage at Stone Tower Winery just outside of town offers a contrasting, country experience. Besides being into wine, this vineyard setting is great for those looking for more space, a. countryside ambiance and sunsets over the vines. The pergola and firepit offer slam-dunk private, romantic spaces-for-two. 

Choosing a base for your romantic getaway is personal. Whether splurging to be in the center of things with walkability or succumbing to the quiet charms of wine country — both options present an idyllic setting.