Take a short scenic ride west from DC to discover this walkable, picturesque town.
FOR THE GIRLFRIENDS’ ESCAPE
Park the car at The George Washington Hotel and the driving is done until you head home. The hotel is just a stroll from all things downtown, the perfect backdrop for a besties’ catch-up
Plan a leisurely lunch or dinner at Paladin, a funky downtown spot set in a 1920s building notable for original finishes and soaring ceilings. Settle in surrounded by eye-popping art, order a craft cocktail or two, and share some inventive nibbles. Tuck into a Southern fried chicken skillet with country gravy or, on the lighter side, the Hawaiian-style tuna poke bowl.
Browse the Old Town Loudoun Street Pedestrian Mall, which stretches two long blocks between Piccadilly and Cork streets. Peppered with locally owned retail, this is where you can get your feet measured, old-school style, at Wilkins’ Shoe Center, outfitting family feet since 1947. The indie Winchester Book Gallery spotlights local authors, while Mountain Trails is a go-to for trekkers on the Appalachian trail. Galleries and boutiques spotlight regional designers, Virginia watercolors, and found object art.
Make a few stops along the Winchester Beer and Cider Trail, which offers a handful of downtown stops for microbreweries, cideries, and breweries. Visit downtown dining spots like Village Square Restaurant and Water Street Kitchen where you can try local ciders.
Be sure to make an appointment at The Ritual Spa in the hotel before your trip. Try one of their specialty treatments—the ethereal balance massage is a supreme stress buster.
Before hitting the road, get a ginormous MaWilt’s Big Pancake with blueberries or the brisket and eggs at Bonnie Blue Southern Market and Bakery, a final taste of Winchester hospitality.
Where to Stay
The George Washington, a Wyndham Grand Hotel, has sheltered travelers since 1924. The Georgian Revival hotel combines modern amenities with a stellar location and historic details to spare.
FOR THE FARM-TO-TABLE FANS
There’s nothing new about farm-to-table in these parts. The Shenandoah Valley has long been an agricultural hub. From acres of orchards to small, family-owned farms, the Valley’s produce and animal husbandry are legend. Visit between June and October and traverse ribbons of back roads outside town, visiting places like Marker Miller Orchards, West Oaks Farm Market, and Richard’s Fruit Market to the west of Route 11.
What better way to lower the blood pressure than watching baby goats frolic and sampling an abbondanza of apples? Winchester, once known as the apple capital of the world, is still the largest grower of apples in the state. The annual Shenandoah Apple Blossom Festival draws thousands to town each spring.
Back in Winchester, chefs and bakers are innovating with local ingredients that highlight the region’s rich terroir. At T.T. Walls Kitchen & Bar, a contemporary Southern concept named for the former on-site haberdashery, executive chef Jeffrey Wilson creates shapeshifting dishes like collard greens risotto and saffron PEI mussels with okra and hominy. The same owners are behind The Wine Room at Taylor Pavilion around the corner, an intimate spot for a nightcap.
Bistro Sojo is another brilliant option for dinner, opened less than a year ago by chef-owners Martha and Felix Addison. The restaurant glows with hospitality and warmth, with a menu of Mediterranean cuisine. The owners, who hail from Tanzania and Ghana, make it their mission to shine a light on lesser-known gastronomies, including Moroccan, infusing many of the dishes with West African flavors.
At the aptly named Knead Bread, an artisan bakery and breakfast spot just off the pedestrian mall, sip on locally roasted Low Note coffee, ideally paired with irresistible pastries spiced with the likes of cardamon and nutmeg. Of course, apples, in all their iterations, are folded into pastries both sweet and savory.
FOR THE HISTORY AND CULTURE BUFFS
History wags like to recount lore about where our nation’s first president overnighted. For sure, George Washington slept in Winchester, where he spent the better part of a decade during his early surveying career. Between May and October, history buffs can take an Old Town Winchester guided history tour for extra background. That tiny log cabin building close to the Pedestrian Mall is George Washington’s Office Museum. It’s a good idea to make the Winchester-Frederick Country Visitors Center on the outside of town a first stop for maps, self-guided tour info, and general history.
The region is also rife with Civil War history. The Shenandoah Valley Civil War Museum, housed in the historic Frederick County Courthouse once used as a wartime hospital, prison, and barracks, provides outstanding context. The upstairs galleries include poignant graffiti etched into the walls by POWs, including a particularly vivid curse upon Confederate president Jefferson Davis.
From a more artistic perspective, the Museum of the Shenandoah Valley bears witness to the effect the valley’s landscape had on artists both from the region and around the world. Stretch your legs before or after with a ramble through the museum’s gardens and walking trails.
Winchester’s pop culture cache is solidified at the Patsy Cline Historic House, where the country star lived from ages 16 to 21. But music doesn’t just inform Winchester’s past. Future stars are primed at Shenandoah University’s conservatory, an arts-based community of more than 600 students who perform at the Ohrstrom-Bryant Theatre.
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