Welcoming visitors with warm hospitality for over 250 years, Old Town Winchester hosts over 30 restaurants, 60 shops and numerous historic sites and museums. With a newly renovated walking mall, shopping in Old Town Winchester is an experience to be savored. Old Town is sure to have just what you are looking for – an eclectic mix of antiques, fine furnishings, gift items, local and regional works of art, and fine clothing. Download the Old Town Winchester APP for free to browse what downtown has to offer or to follow a free self-guided walking tour.
Enjoy a variety of restaurants featuring outdoor cafe dining, or dine in and enjoy the ambiance of our many historic settings. From Mid-May through Halloween enjoy shopping at the Old Town Farmers Market in the Taylor Pavilion. A visit to Old Town Winchester would not be complete without a stop at Stonewall Jackson’s Headquarters Museum, George Washington’s Office Museum, the Old Courthouse Civil War Museum, and the Shenandoah Valley Discovery Museum. History buffs may want to take a guided walking tour featuring beautiful architecture and local history.
Old Town Winchester is located within the heart of our 45-block National Register Historic District and features a quaint pedestrian walking mall bursting with outdoor cafes, fun shops, specialty retail shops 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 as a place that successfully combines history, century old buildings and museums with the vitality of an ideal downtown – creating a charming and sophisticated downtown atmosphere.
Old Town Winchester hosts many activities throughout the year including; First Fridays Celebration of the Arts (monthly), Friday Night Live, Shenandoah Apple Blossom Festival (May), KidzFest (May), Free Family Movies(Summer Thursday Nights), Bluemont Summer Concert Series (summer Friday nights), Downtown Tailgate (September), Octobeer Fest (October), Christmas in Old Town events including the City of Winchester Parade (December), and the New Years Eve First Night Winchester celebration.
Whether you are new to Winchester, one of our treasured guests for a day or a week, or a native hoping to rediscover your past – come to Old Town Winchester to tour, shop, dine, wander, relax and revel, and experience the best that Winchester has to offer. When visiting downtown Winchester, be sure to visit the Welcome Center at 33 E. Boscawen Street.