A vital marketplace for more than 250 years, Old Town Winchester cherishes its heritage. Visitors are welcomed here with the grace and style typical of Virginia hospitality. Old Town Winchester is located within the heart of a 45-block National Register Historic District and features a quaint pedestrian walking mall bursting with outdoor cafes, fun & specialty retail shops, historic attractions and family-oriented activities throughout the year.

The Loudoun Street Pedestrian Mall has earned a listing on the National Register of Historic Places Travel Itinerary. A 7 million dollar renovation of the Mall was completed in 2013.

Old Town Winchester is a great place to stroll and window shop, find a unique gift, or something special just for yourself. Shoes, jewelry, art, home décor, musical instruments, books, antiques, and so much more await your visit!

Dine in Old Town and experience local fare! From casual sports pubs to fine dining and international cuisine – there is something for every taste. In the warmer months, most offer outdoor dining, where you can eat a leisurely meal and enjoy watching the activity along the walking mall.

A visit to Old Town Winchester would not be complete without a stop at one of the museums located in the historic district. Stonewall Jackson's Headquarters Museum, George Washington's Office Museum, the Old Courthouse Civil War Museum, and the Shenandoah Valley Discovery Museum (children's museum) are located within a comfortable walking distance of each other and convenient parking.

Arts & Entertainment
Old Town Winchester hosts many annual activities including First Fridays Celebration of the Arts (monthly), Shenandoah Apple Blossom Festival (May), Bluemont Summer Concert Series (summer), Free Outdoor Movie Series (summer), Christmas in Old Town events (December), and the New Year’s Eve First Night Winchester celebration. The Shenandoah Arts Council, Magic Lantern Theater, and Winchester Little Theatre offer opportunities to
experience the arts in Old Town Winchester year-round.

The restaurants and bars around Old Town are a favorite spot for nightlife. Most offer live music on weekends and are easily within walking distance of one another.

Walking Tours
Experience life during the Civil War, or admire centuries of history and architecture on a walking tour. Both guided and self-guided tours of the historic district are available. See our Tours and Itineraries page for more information. Call the Visitors Center at (877) 871-1326 for guided tour schedules, or pick up self-guided tour brochures at the Visitors Center, 1400 S. Pleasant Valley Road.


Old Town Winchester
1 N. Loudoun Street
Winchester, VA 22601
(540) 667-1815

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