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What’s Up in the Gap

The Greater Hillsboro region remains open for business throughout the construction period and the Town is committed to providing visitors with updates and information on special events and activities at the nearly 20 vineyards, wineries and breweries and the wide variety of farms, farm markets, B&Bs and restaurants in “The Gap.”

Explore Local Businesses


Hillsborough Bed & Breakfast

Hillsborough B&B is a country retreat located outside the historic town of Hillsboro in the heart of Northern Virginia’s wine region. The original home was..

36933 Charles Town Pike, Hillsboro, VA 20132

Hill Tom Market

Small Hillsboro-based country store offering hot and cold sandwiches, beer, wine, drinks and snacks.


Hidden View Bed & Breakfast

Hidden View Bed & Breakfast — a luxury B&B, boutique resort, event venue, and vacation rental in Northern Virginia — was voted Best of Virginia..


Harpers Ferry Brewing

Located in Virginia along the banks of the Potomac River with views of West Virginia and Maryland. You will find us at Route 340 &..


Fieldstone Farm Bed & Breakfast

One of the largest and finest homes in the small, historic town of Hillsboro, Virginia, Fieldstone Farm was built before the town was formally established..


Doukenie Winery

We feature a wide selection of award-winning releases and an ever-changing seasonal portfolio. Guest favorites include Merlot, Sauvignon Blanc, Riesling, Cabernet Sauvignon, and popular Bordeaux-style blends. Our..


Crushed Cellars

Crushed Cellars is a family-owned and operated farm winery that is passionate about fine wine. The tasting room has a warm and fun atmosphere and..


CEA Farms

Loudoun’s farming roots go deep—there’s a reason this county was called “The Breadbasket of the Revolution”—and no one is more in touch with those roots..


Bozzo Family Vineyards

As the name of our vineyard suggests, family is a primary focus of our vineyard and winery, along with high quality, approachable wines, and simplicity..



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Town of Hillsboro, 37098 Charles Town Pike, Hillsboro, VA 20132

(540) 486-8001