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Winchester, VA Uncommon to the Core

A mural in downtown Winchester.

The Civil War, apples and Patsy Cline. While these are generally considered the biggest draws to the city of Winchester, VA, there’s truly a surprise around every corner. From enjoying bourbon flights at one of the Top 10 bourbon bars in America, to dining on mouth-watering ribs at a gas station restaurant, to whiling away an evening watching live bluegrass in a farm market parking lot, Winchester truly lives up to its slogan—Uncommon to the Core.

For foodies, the area teems with opportunities from its farm markets to its higher-end dining establishments. And who wouldn’t love a classic southern breakfast served in what used to be a working garage?

Bonnie Blue Southern Market & Bakery is one of the many surprises along the Gas Station Grub Trail.

The Gas Station Grub Trail features some of the area’s most tasty treats in the most unique settings you can imagine, dishing out Texas twinkies, brisket, sausage gravy and more in 13 repurposed service stations throughout Frederick County. Stop in to Riley’s ChiCorkFish (“Chicken, Cow, Pork and Fish, It’s Who We Are, It’s What We Fix”) for a hearty Boss Hogg Platter or start your day off right at Bonnie Blue Southern Market & Bakery, located in a 1921-built Chrysler showroom. Their bakery, which is built over the station’s former oil pit, offers decadent baked goods, and their elevated barbecue has earned them a New York Times recommendation as one of 13 Essential Barbecue Stops.

The area abounds with farm markets, as well as wineries and meaderies that produce delicious libations made from local crops. Briedé Family Winery, for example, not only produces wines made from organically grown and biodynamic grapes, but serves locally crafted wine ice cream at their stunningly converted horse barn that now serves as a tasting room. Misty Mountain Mead, the oldest operating meadery in the state, uses Virginia honey to make Wildflower Mead, Lemon ‘n Honey, Butterscotch ‘n Honey, Hazelnut ‘n Honey mead and more—and owner and meadmeister Richard Copeland is a wealth of information on the history of the world’s oldest alcoholic beverage.

The Vault & Cellar’s Vault Burger, made with peanut butter, bacon and housemade chow chow.

If you’d like to take freshly grown produce and farm products home with you, Frederick County offers everything from Geraghty’s Micro Farm, which has a small farm market on site, to The Homestead Farm at Fruit Hill Orchard, a fifth-generation farm that hosts a homemade country dinner and free bluegrass concert every Thursday evening during the summer and fall. And if you’re lucky, you might even win the raffle and take home a bag of homegrown apples! Winchester Ciderworks also shares the same parking lot, so you can add a traditional English-style dry cider tasting to the agenda if you choose.

For a more sophisticated meal, The Vault & Cellar Restaurant in Middletown offers a taste of New Appalachian cuisine combined with a hard-to-beat bourbon bar, showcasing 250 whiskeys and 200 bourbons among other offerings. Chef Kari’s menu, which changes seasonally, features everything from fried catfish to shrimp and grits, to wild boar sausage and Long Meadow duck, so be prepared to taste something unique while enjoying the thoughtfully curated bourbon collection.

A costume at the Patsy Cline Historic House.

While it would be possible to spend an entire visit to Winchester eating and drinking your way through town, it wouldn’t be right to visit the hometown of Patsy Cline without stopping by her childhood home and learning about the short-lived country singer’s life. Raised in near-poverty by a single mother, Cline got her big break in 1957 and left behind a legacy of amazing work during her eight-year career before dying in a plane crash at the age of 31. It’s touching to see where the young singer grew up, especially the dining room where her mother made her earliest costumes by hand.

Another must-stop is the Museum of the Shenandoah Valley, which truly features something for everyone. In addition to rotating national and regional exhibits (including Sean Kenney’s Nature Connects® made with LEGO® Bricks coming in May), it includes the Glen Burnie House and Gardens, where you can take a self-guided tour through formal gardens as well as an Asian-inspired bamboo forest. A free-admission art park is part of the recently opened trail system which allows visitors to wander throughout the museum’s 90 acres.

The museum itself has a number of permanent collections, including the Shenandoah Valley collection, with items representing the history and people of the region, and the R. Lee Taylor Miniatures Collection, which includes some of the finest examples of miniature homes and decors of the 1920s-2000s.

Before heading back home, stop into the Hideaway Café in Old Town’s pedestrian shopping mall for Winchester’s Best Coffee (Star Award Winner, 2019, ’20, ’21) an LGBTQ-owned business where everyone is welcome. Located in an 1827 building, the coffeehouse even has its own ghost—a bluegrass player who changes the radio station when he doesn’t like the music.

To learn more about Winchester, VA and all of the unique places to go, visit Discover Winchester Virginia at

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