Nestled in a gap in Short Hill Mountain, Hillsboro, established in 1802, is one of the best-preserved rural towns in the country with historic fieldstone buildings hugging Route 9 and giving it the look of a medieval European village. The surrounding vine-covered slopes are home to some of the finest wineries and breweries, and a slate of boutique B&Bs have opened.


Must Do:

Wine Tasting

Some eight wineries make up the Loudoun Heights Cluster around Hillsboro, including 2020 Governor’s Cup winner 868 Estate Vineyards, and the scenic 400-acre Doukénie Winery. On slopes facing the Blue Ridge, you will find Hillsborough Winery Brewery & Vineyards and the French-Louisiana style tasting room of Breaux Vineyards. Don’t miss the subterranean cellar of Maggie Malick Wine Caves further west.



Beer We Go

Harpers Ferry Brewing on a hillside in far northwest Loudoun has spectacular views of the Potomac River and Harpers Ferry from its shaded decks. Try the summery, citrus-forward Potomac Pale Ale. Alongside their wines, Notaviva Craft Fermentations does a slate of superb farm brews including a popular Old Steeleye Nut Brown Ale.



Produce & Picnics

Fans of fresh produce will love the local veg, meat, poultry and dairy at Stoneybrook Farm and Market, some of it grown on a 45-acre farm in the center of town. For a ready-made basket of delicious local products – cheese, bread, cured meats, salads, wine – order a gourmet picnic basket from the Hillsboro-based Virginia Picnic Basket Co.




Zip lining, aerial ropes courses, and tubing, kayaking or rafting the Potomac or Shenandoah rivers all await visitors at Harpers Ferry Adventure Center. Part of the same property as Harpers Ferry Brewing, you won’t go thirsty, either.




Why make a day of it when you can spend the night? Hidden View Bed & Breakfast is set on 10 acres of rolling grounds with Blue Ridge views and an inviting swimming pool.



Not to Miss Events

Music in the Gap, July-August

This much-loved summer concert series takes place Friday nights at the Old Stone School in the heart of town, July through August. Bands slated to appear in 2021 include Todd Brooks & Pour Decisions, and country roots band Hard Swimmin Fish. Grab a seat on the veranda or lawn and soak up the sounds.


LoCo Musicians Festival, September

Award-winning 868 Estate Vineyards hosts numerous music events throughout the year, but the highlight is this extravaganza each September featuring some 35 musicians playing with their bands or in collaboration with other groups to raise money for equipment for local musicians. We’ll raise a glass of wine to that.


Hillsboro Gardens in the Gap, April

Every April the Old Stone School hosts this spring rite of passage featuring everything from arts, crafts and native plant sales to guest speakers. Over the weekend, historic local estates open their gardens to visitors.