Nestled In Virginia's Blue Ridge Foothills Is A Revived Village With Vineyards, Scenic Views, And Rustic Charm

Virginia's Blue Ridge Mountains are a treasure trove of outdoor adventures and thrilling activities. But along its foothills, you'll also find some of the best mountain towns where you can discover hidden gems and unique experiences. Take Hillsboro in Loudoun County, that county's smallest incorporated town. Originally known as The Gap, referring to its location in the gap in the Short Hill Mountain, the town is easily located along Virginia State Route 9, where the community had its humble beginnings in 1802. 

Hillsboro has a rich history and a tight-knit community that works to preserve its heritage. Here, you can step back in time to what appears to be an 18th-century village, with many buildings preserved from its original construction. The district is also listed on the National Register of Historic Places and is known as one of the best-preserved rural towns. With only about a hundred residents as of 2025, Hillsboro is primarily a residential community where most locals know each other. 

However, its location in the Loudoun Heights Cluster means it's surrounded by tons of wineries, vineyards, and breweries that draw in the visitors. Outdoor adventures are also just a quick trip from Hillsboro, like the Appalachian Trail. So there is a mix of locals and tourists who pass by the small town destination for the scenic views, local dining, and wine trails. Their proximity just east of the Blue Ridge Mountains means there are also plenty of opportunities to see views of the stunning mountains.

As Washington, D.C.'s dazzling wine country, Loudoun County is one of the best places to start your Virginia wine trail. In the area around Hillsboro, you'll find 22 vineyards, wineries, and breweries within 10 minutes of the small town. Start your journey with 868 Estate Vineyards, which won the Virginia Governor's Cup award in 2020 and greets you with forests, meadows, and rolling hills on its legacy farm. Their tasting room also doubles as an art gallery that shines a light on local artists' work and changes throughout the season. Music is also a big part of the experience at 868, with concerts and music events happening all year round. Their biggest event is the annual LoCo Fest, featuring about 30 artists performing. 

If beers are more your vibe, head to the oldest brewery in Hillsboro, Old 690 Brewing Company, which is one of the first licensed farm breweries in the county. They focus more on small-batch brews of IPAs, stouts, porters, and seasonal choices. 

For a bit of everything, Hillsborough Winery, Brewery, and Vineyard is an all-in-one spot with both wine and beer on offer. This family-owned and operated business has been thriving for three generations and features drinks made from quality ingredients. Their location also offers the scenic landscape of mountains, valleys, and sprawling vineyards. Choose to spend your downtime in their cozy indoor space, semi-covered outdoor patio, or the open areas. If you're heading down south, there are more villages with picturesque vineyards in the mountains that you could explore. Don't miss the Monticello Wine Trail that blends award-winning wines with centuries of history.

Hillsboro is easily accessible and is only a quick day trip from the District of Columbia, coming at an hour and a half's drive, depending on the traffic. You can also take the Metro Silver Line to Ashburn station, only a half hour's drive from Hillsboro. Or if you're flying in from farther away, the Dulles International Airport is only 45 minutes away. 

If you're staying for more than just a day trip, there are a couple of great options for accommodations in Hillsboro. The Hidden View Bed and Breakfast is a luxurious option where you can wake up to the views of the Blue Ridge Mountains each morning. The bed and breakfast sits farther from the town center and atop Short Hill Mountain. Another option is Silverbrook Farm, an event venue turned bed and breakfast that also offers panoramic views for your mornings. The farmhouse and property had their start in 1765, and like many of the buildings in Hillsboro, it's been well-preserved through the ages. 

While you're in Hillsboro, don't forget to stop by any of the local shops and boutiques. One that you should visit is the Stoneybrook Farm Market, a marriage of farm, deli, market, and bakery all in one spot. You'll find them on a 45-acre organic farm from Sundays to Fridays. They offer freshly baked bread, sandwiches, and farm-fresh produce. If you're looking for something to bring back home, their market offers more than food, including pottery works and body care.