Tucked In Virginia's Shenandoah Valley Is A Quaint City Of Tree-Lined Cobbled Streets And Historic Charm

Although there's no shortage of vibrant cities with charming cobblestone streets in America, a little Virginia gem in the Shenandoah Valley that you've likely never heard of beckons for exploration: Winchester. This historically rich city is known for its quaint shopping centre in the Old Town, a plethora of important American landmarks, along with museums and other amenities — it deserves a spot on your Virginia bucket list.

Originally named Frederick Town, in the mid-1700s, Winchester became a political and military training ground for George Washington, who also built the iconic Fort Loudoun (which still stands today). Though the story of Washington chopping down a cherry tree is a myth, the fact that Winchester has a plethora of orchards certainly isn't. In fact, no region in Virginia produces more apples than the city of Winchester. In the spring, you can take part in the Shenandoah Apple Blossom Festival, where more than 250,000 visitors gather to celebrate Winchester's vibrant spirit and blooming beauty.

Old Town Winchester, the centerpiece of Winchester's expansive National Register Historic District, will take you back 250 years. Striking architecture, including the grand Frederick County Court House, will surely catch your eye. As you'll read below, shoppers and museum enthusiasts are especially in for a treat when visiting this cultural gem of a city.

Virginia undoubtedly deserves a place among the best states for budget-friendly shopping. In Winchester, Old Town's Loudoun Street Pedestrian Mall has overcome a host of challenges over its history to become one of the city's prime gathering spots. Its quaint shops, galleries, breweries, and restaurants have something for everyone.

Grab a great read at the Winchester Book Gallery, fuel up with a cup of coffee at The Hideaway Café, or enjoy mouth-watering handcrafted mini-burgers at the popular Old Town Snow White Grill. To boot, a public splash pad in the Old Town is sure to keep the kiddos cool and entertained. "This little town/city has many well-preserved buildings from its 19th-century heyday. The quiet, pedestrianized main street makes for a delightful walk. Many places to eat, too," effuses a Tripadvisor user.

Visitors wax lyrical about affordable pricing on everything from lodging and dining to pottery. For travelers watching their wallets closely, Winchester is a welcome alternative to Virginia's more expensive destinations — think Alexandria's upscale boutiques, Arlington's high-rise luxury, or Charlottesville's university-town splendor. Loudoun Mall celebrated its 50th anniversary in 2024, and there's no doubt this walkable mecca for shopping and dining has a bright future ahead.

If history and culture are your thing, Winchester offers a variety of museums that make for a great day trip — some of which can be considered among the best free museums in America. At Fort Loudoun in Winchester, you can examine the surviving elements of George Washington's headquarters from the French and Indian War, including the original well and remnants of the bastion. Admission and tours led by friendly docents are free of charge.

The Museum of the Shenandoah Valley, which is situated on land originally claimed by Winchester founder James Wood in 1735, features a wealth of exhibitions that chronicle the area's dynamic past. At the time of writing, the museum's trails are open daily, while the galleries and gardens are open Tuesday through Sunday (closed Monday). For the perfect place to unwind with a book amid architectural surrounds, check out the circa-1913 Beaux-Arts style Handley Regional Library.

If you've got children in tow, they'll be sure to love the interactive exhibits at the Shenandoah Valley Discovery Museum, which hosts summer camps and other year-round events. After a long day of sightseeing, you can indulge in comfort at the 100-year-old Georgian-Revival George Washington Hotel, with its stately pool, two fantastic restaurants, and stress-melting spa. For commercial flights, the nearest airport is Washington Dulles International (IAD), about an hour away by car from Winchester.