A City After Washington’s Heart

Like the visionary Founding Father, Winchester is building a new future.

Photography by Ryan Donnell

George Washington left his mark throughout the Commonwealth, from his childhood in the Tidewater, to governing in Williamsburg, until his final days at Mount Vernon. It is perhaps less well known that from 1748 to 1758, the future president spent the majority of his time in Winchester, a frontier town in Frederick County. 

George Washington Statue & Washington’s Office Museum.

There, beginning at age 16, he honed his skills as a surveyor, commanded the Virginia militia, built a strategic fort, and won his first political seat, representing the county in the House of Burgesses. Washington saw Winchester as essential to the fortification of the Republic, and one of his first acts was to ban pigs from running through the streets of downtown. 

Always a visionary, Washington would surely delight in Winchester today. For more than 250 years, the pedestrian mall in the heart of the National Historic District has remained a vibrant marketplace where people shop and dine. The city has safeguarded architecturally notable buildings and protected the farmland blooming with Frederick County’s signature apple trees.

If You Build It…

Mayor John David Smith Jr. (right) with his partner of 30 years, Joerg Eichmann.

Decades ago, Winchester’s top draw was its rich historic sites, including Washington’s office and several Civil War battlefields. But as the region has grown, forward-thinking business owners have begun developing new and captivating venues, driving the transformation into a more well-rounded and energetic community. 

John David Smith Jr., Winchester’s two-term mayor, spearheads the movement to reimagine the city as a destination. “Winchester used to be a sleepy little city that was basically known for its Civil War history. But we also want to talk about all the fine shops that we have here, the restaurants, and the different events. Winchester was always known for apple blossoms, but now there’s CelebraciÓn Winchester for Hispanic Heritage Month, the African American Heritage Driving Tour, and the Shenandoah Museum, which has different activities. These efforts are bringing more people to see what Winchester has,” says Mayor Smith. 

As the owner of Water Street Kitchen and Village Square Restaurant & Martini Bar, the mayor enjoys chatting with tourists. “We always ask people how they decided on Winchester. They tell us friends told them about the venues, the hotels, the walking mall, which is a big draw because we are one of only two walking malls in Virginia.”

Stretch Your Legs

Smith is an avid cyclist and declares Winchester’s roads ideal for exploring the countryside. “I ride the Green Circle Trail through the city, then head out toward the county.” He also praises the new art trail at the Museum of the Shenandoah Valley (MSV). “The museum is Winchester’s Central Park, because you can go there and be among the wilderness. To enjoy the peace and quiet and still be in the city.” 

“My Friend Red” sculpture at MSV Art Park.

A jewel among Virginia’s extensive museum collection, the MSV complex is home to Virginia’s largest outdoor art park, a modern museum that houses Shenandoah Valley artifacts and contemporary art, and the Glen Burnie House & Garden. The complex occupies land once claimed by Winchester’s founder, James Wood. His descendant, Julian Wood Glass, Jr., acquired the ancestral home, Glen Burnie House, and, with his partner, R. Lee Taylor, fashioned the property into an exquisite estate. 

Upon his death, Glass bestowed public access to the house and gardens, including the couple’s collection of decorative arts and handcrafted miniatures. “These miniatures were Lee Taylor’s passion, along with the gardens,” says Julie Armel, deputy director of community relations for the MSV. Taylor acquired pieces made by the greatest miniature artists of the time, she says. “The miniature inside the Glen Burnie House is an exact replica of what the house looked like before it was opened to the public. It has incredible detail, like writing in the books, and wine bottles with the actual vintage.” 

In the estate’s opulent gardens, stroll through the Rose Garden, the Statue Garden, the Pink Pavilion, with its tunnel of trees, and most spectacular of all, the Asian Garden, with its rustling bamboo grove. 

Old Town Winchester

If all that walking inspires your appetite, check out Sexi-Mexi, where chef Cristina Willis creates cross-cultural bowls and burritos like Caribbean Jerk Chicken, Crazy Cuban, and Voluptuous Vegan. For authentic Southern comfort food, try Water Street Kitchen for the mayor’s favorite Reuben sandwich or tasty appetizers like sweet corn hush puppies and fried pickles; the Daily Quiche and Josie’s Grilled Cheese and Tomato Soup also earn raves. Just outside of town is The Butcher Station, a culinary-forward steakhouse that sources its free-ranging, all-natural meats from nearby Audley Farm—which, in another George Washington connection, was owned by members of Washington’s family for 138 years.

Oven roasted bay rock fish at George’s Food & Spirits in the  George Washington Hotel.

The first president is also honored by the historic hotel that bears his name. The George Washington Wyndham Grand Hotel offers the city’s premier accommodations and is celebrated for its Roman bath-style pool and fine restaurant, George’s Food & Spirits. Chef Will Mason, who trained at Johnson & Wales University, showcases locally grown products in award-winning ways—his Bay Rock Fish is legendary, and the Southern Benedict with Fried Green Tomatoes is a perfect start to the weekend.

You can also indulge in retail therapy on the streets of Old Town, with its array of independently owned boutiques, furniture, and bookshops. In particular, Handworks offers a tempting stock of jewelry and handmade pottery, some created by Shenandoah Valley artisans. If you’re looking for gifts, peruse Kimberly’s, a historic manor transformed into a shop with stylish clothing and home goods. 

The insightful exhibits at the Shenandoah Valley Civil War Museum can keep history buffs occupied for hours. The former Frederick County Courthouse served as a prison and barracks for both Union and Confederate Armies during the Civil War, and some soldiers left graffiti on the walls. At George Washington’s Office Museum, a statue of the young George stands in front of the oldest surviving building in Old Town. For the kids, there’s the Shenandoah Valley Discovery Museum and Old Town Splash Pad. 

A Little Something To Drink

A number of craft beverage makers call the area home. Located inside a converted circa-1900 apple barn, Winchester Ciderworks is the brainchild of an apple farmer and an Englishman who missed traditional British cider. The team takes advantage of the region’s plentiful apple harvest to produce an array of flavored and seasonal hard ciders. Misty Mountain Meadworks is the oldest operating meadery in the state (open by appointment). James Charles Winery offers Old World-style wine and appetizers in a stylish tasting room or on the stone patio (equipped with fire pits for cold days).

Shawn Steffey pouring at The Wine Room at Taylor Pavilion.

At Briedé Family Vineyards, owners Loretta and Paul Briedé embrace sustainability and disease-resistant grapes to make their organic wine and rare varietals. “We grow grapes that aren’t heavily planted in Virginia, like Cayuga and Arandell,” explains Loretta. And they’ve had triumphs. Briedé’s Sparkling Winchester won a silver medal in the 2020 Virginia Governor’s Cup competition and the 2019 Arandell earned a silver medal in California’s Sommelier Challenge. 

Although you can visit Valerie Hill Vineyard & Winery in nearby Stephens City, you can also experience the wine in downtown Winchester. Seeking a new way to connect with wine lovers, owner Shawn Steffey debuted The Wine Room at Taylor Pavilion, which offers over 70 wines by the glass. “We want you to expand your palate and go outside your comfort zone. You don’t have to drink chardonnay all the time,” he laughs. The Wine Room is equipped with garage-door-style windows that open to Taylor Pavilion, an amphitheater used by the city for live music and movie nights. “This whole wall opens up, which is why we created a seating bar to enjoy the entertainment,” says Steffey. 

Nearby Adventures

For those seeking thrills over chill, drive 12 miles to the base of Great North Mountain to play at The Cove Campground. The privately owned, 3,000-acre tree farm is where you’ll begin your Appalachian Offroad Adventure (AOA) with owners Angela and Mikel Welling. 

Bamboo grove in the Asian Garden at the Museum of the Shenandoah Valley Art Park.

While many Jeep tours involve riding, AOA is different. “With us you’re driving your own Jeep, making your own decisions,” explains Mikel. “There are moments when you’re scared and tippy. There’s water, mud, rocks, inclines, lots of trees. It can feel like a rollercoaster if you’re new to it.” After the ride, guests are welcome to camp, fish, hike, and swim. 

Before heading home, stop by the West Oaks Farm & Market, just south of the city. The farm has been in the Snapp family since 1775, and they recently expanded the market. “When we first started, people came for the produce, because we are a farmers’ market, and then for our locally sourced meats and dairy products,” says market manager Levi Snapp. “But now we operate a cafe, sell some alcohol, and have special events on the side.” There’s also a play space to keep the kids happy so grownups can sample cider from Winchester Ciderworks.

Like the Snapp Family, George Washington acquired land from Thomas Lord Fairfax in the 18th century. Through commerce and commitment to the wellbeing of future generations, Frederick County has prospered. Perhaps these denizens of Winchester inspired Washington’s words in 1790, “Make us all in our several vocations useful here, and in his own due time and way, everlastingly happy.” 

Make It A Weekend

Winchester-Frederick County Visitors Center: In addition to brochures, this well-equipped visitor center provides a gift shop, playground, walking trails, and an overview of Frederick County’s role in the Civil War. The Becoming Patsy Cline exhibit showcases the life of Winchester’s hometown singer. 1400 S. Pleasant Valley Rd.; 540-542-1326 or 877-871-1326; VisitWinchesterVa.com/visitor-center

  • George Washington, a Wyndham Grand Hotel: The hotel offers an ideal location for walking around the National Historic District. Guest rooms and suites are large and well-appointed; some have a fireplace. Amenities include live entertainment on weekends, an indoor pool, a spa, and restaurant. 540-678-4700; WyndhamHotels.com
  • Pembroke Springs Retreat: A rental villa with two private Japanese baths fed by natural springs and five guest rooms, all with panoramic vistas. Accommodates up to 10 guests with a kitchen, game room, tennis courts, and fully stocked fish pond. 540-877-2600; PembrokeSprings.com 
  • The Butcher Station: A sister/brother team owns this culinary-focused butcher shop and restaurant featuring meats and handmade products from craftspeople in the Shenandoah Valley. TheButcherStation.com

Sexi-Mexi Burrito Bar

  • George’s Food & Spirits: For breakfast, look for traditional Eggs Benedict as well as options like the Quinoa, Egg & Avocado Bowl. Most notable at dinner—Oven Roasted Bay Rock Fish and Mason’s Apple Pie Spring Rolls. Enjoy romantic dining on the sunken patio. WyndhamHotels.com
  • Sexi-Mexi Burrito Bar: This small, stylish eatery serves hefty burritos, bowls, and snacks in a fusion of cross-cultural flavors. Check out the inventive craft cocktails at happy hour. BurritoBar-Sexi-Mexi.com
  • Water Street Kitchen: Known for Mid-Atlantic favorites and “down-home cooking,” this generously portioned comfort food is great for groups. Craft beers and wine available with a corkage fee. WaterStKitchen.com
  • Briedé Family Vineyards: Briedé offers special events throughout the season, such as a Mother’s Day Extravaganza, Sexi-Mexi Food Truck, falconry, Dinner in the Vines, and a Shrimp Boil. Private tastings arranged with advance reservations. 540-664-2048; BriedeVineyards.com

Flights at Winchester Ciderworks.

  • James Charles Winery: Floor-to-ceiling windows provide mountain vistas while wine consultants guide your choices among their Cabernet, Ameritage, Cuvée de la Reine, and others. 540-931-4386; JamesCharlesWine.com
  • The Wine Room at Taylor Pavilion: This urban wine bar is located one block from the pedestrian mall in Old Town overlooking the Taylor Pavilion, an outdoor venue with live music and movies. 540-686-0545; TaylorWineRoom.com
  • Winchester Ciderworks: Visit the converted apple barn for aged and specialty hard ciders. 540-686-7632; WinchesterCiderworks.com
  • Appalachian Offroad Adventure at The Cove Campground: This new guided Jeep tour experience allows guests to steer through obstacles to reach panoramic vistas. Book a cabin, bring your RV, or raise a tent at one of the primitive campsites.  980 Cove Rd., Gore; 540-333-6875, AppalachianOffroadAdventure.com
  • George Washington Statue: & Washington’s Office Museum: The oldest building in Old Town likely served Washington’s surveying office when he planned the construction of Fort Loudoun (1756-1758). WinchesterHistory.org
  • The Green Circle Trail: This 12.5-mile moderately trafficked loop trail is used by dog walkers, runners, and cyclists. Download a trail map at WinchesterVa.gov.
  • Museum of the Shenandoah Valley Art Park: Paved, ADA-accessible trails are free and offer views of the Shenandoah Valley, the city of Winchester, and the Blue Ridge Mountains as well as impressive outdoor art installations. A new boardwalk over the wetlands section was recently added. 888-556-5799; TheMSV.org
  • The Museum of the Shenandoah Valley’s Glen Burnie House & Gardens:  Part of the MSV complex, the serene and inspiring estate has walking paths through manicured gardens and a historic manor filled with an impressive decorative art collection. 888-556-5799; TheMSV.org
  • The Old Stone Church/Winchester Colored School:  Originally built in 1788 as a church, Revolutionary War hero General Daniel Morgan is buried here. In 1875-1929, it served as a schoolhouse for African-American students from the upper Shenandoah Valley. PCWinc.org
  • Shenandoah Valley Civil War Museum: Housed in the circa-1840 Frederick County Courthouse, this museum provides an insightful look at the lives of soldiers fighting the Civil War. CivilWarMuseum.org
  • Shenandoah Valley Discovery Museum: This STEM-oriented learning museum has a variety of exhibits and events that families will love, like the Apple Processing Plant, Bee Keeping, and Rescue Units. The upper level has a rooftop with charming views of the historic downtown. Best for kids under 10. DiscoveryMuseum.net

Kimberly Sowers at her shop, Kimberly’s.

  • Handworks Gallery: Handcrafted jewelry, apparel, skin care products, pottery, paper, arts and crafts, gifts, and gourmet food made by American and Fair Trade Global artists. HandWorksGalleryWinchesterVa.com
  • Kimberly’s: The historic mansion was used as a military headquarters by General Sheridan and two other Union Generals during the Civil War. Today, it is an elegant marketplace of Virginia-made products, seasonal gifts, home décor, and women’s clothing. Facebook.com/www.kimberlys.biz
  • West Oaks Farm & Market: The Snapp family’s market offers produce, meats, jams, Shenandoah Valley beer and wines, handmade treats, and more. The Café serves lunch and breakfast, with a kids’ play area. WestOaksFarm-Market.com

Renee Sklarew is a journalist specializing in MidAtlantic food and travel. She also leads tours for Smithsonian Associates. Follow her at  @TravelAndDish. This article originally appeared in the April 2021 issue.

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