Old Town Winchester

Loudoun Street Mall

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 beautiful pedestrian mall, shopping in Old Town Winchester is an experience to be savored.

Shopping and Dining

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. Also, enjoy a variety of restaurants featuring outdoor cafe dining, or dine in and enjoy the ambiance of our many historic settings.

Shop, Dine & Explore

Museums and History

Stonewall Jackson Headquarters Museum

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 Attractions

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.

Events and Entertainment

Old Town Winchester hosts many activities throughout the year. Below is a sampling of some of Old Town's major events provided by the City of Winchester, VA(*):

  • Chocolate Escape* (February)
  • Restaurant Week (February)
  • First Fridays* (March-November)
  • Celtic Fest* (March)
  • Shenandoah Apple Blossom Festival (April-May)
  • KidzFest* (May)
  • Hop Blossom Beer Festival (June)
  • Juneteenth Celebration* (June)
  • Rockin' Independence Eve concert and fireworks* (July 3)
  • Skyline Indie Film Fest (September)
  • ShenArts Art Fair (September)
  • Fiddles & Fifths Bluegrass Festival* (September)
  • Celebracion of Winchester (September)
  • Oktoberfest (September)
  • Dia de Los Muertos* (November)
  • WinDependent Weekend* (November)
  • Holiday Open House & Market (December)
  • New Year's Eve Apple Drop (December 31)
  • Old Town Spirit (First Fridays & selected events)

Old Town Winchester Events Calendar

Old Town Mobile App

Old Town mobile app

Download the Old Town Winchester Mobile App for free to browse what downtown has to offer or to follow a self-guided walking tour.

The Old Town Winchester, VA App is available now for FREE on Google Play and the iTunes Store. From the stores, search for “Old Town Winchester” and look for the official seal shown at left.


Jenny McDonald
117 E. Piccadilly St, Ste. 300
Winchester, VA  22601


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