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


Walsh Family Wine

From these hillside sites, we strive not just to produce premium Virginia wines, but premium wine from an international perspective.  With Bethany Ridge and Twin..


Virginia Picnic Basket

We have a Passion for Picnics and we know your time is precious. At Virginia Picnic Basket Company we are here to help you make..


Two Twisted Posts Winery

Our vineyard was established in 2008 and contains blocks of the vinifera Chardonnay, Cabernet Franc and Cabernet Sauvignon and the hybrid Traminette.  We continue to..

34357 Charles Town Pike, Hillsboro, VA 20132

Sweet Springs Country Store

Convenience store located on Route 9 with Liberty gas pumps.  


Stoneybrook Farm Market

We are a 45 acre certified organic farm in rural Loudoun County, Virginia. Our mission is to grow quality local organic crops using sustainable practices…


Paige’s Pit Stop

We have it all!!! Fresh produce, honey, jellys and jams, melons, eggs, vegetables, etc. We are on the corner of Rt.9 & Rt.704 (Hamilton Station..


Old 690 Brewery Co

As one of Virginia’s first limited breweries our goal is simple – to make great beer that brings people together using as many local resources..


Notaviva Vineyard

Stephen and Shannon Mackey share a passion for music and have equally ambitious spirits. They conceived the idea of owning a winery to pair wine..


Maggie Malick Wine Caves

Maggie Malick Wine Caves is a female-owned, boutique winery in Northern Virginia. We feature award-winning, estate-produced wines on 215 rolling acres in the shadow of Short..


Hillsborough Vineyard and Brewery

Experience some of the most scenic views of the Blue Ridge Mountain’s foothills, award-winning wines produced “in harmony with terroir”, quality-crafted beers brewed with the..

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

(540) 486-8001