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

Farmers Market (Closed for 2020)

Enjoy shopping for fresh, local fruits, vegetables, artisan bread and more at the Old Town Farmers Market at the Taylor Pavilion on Saturdays from 9:00 am-1:00 pm, mid-May through September. Located just steps from the Braddock Street parking garage and the downtown pedestrian mall, the market provides convenient shopping and musical entertainment (at noon) most Saturdays.

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)
  • St. Patty's Celtic Fest (March)
  • Shenandoah Apple Blossom Festival (May)
  • Farmers Market (May-September)
  • Friday Night Live concerts (summer)
  • KidzFest (May)
  • Free Family Movies (summer)
  • Classic Movie Nights (summer)
  • Rockin' Independence Eve concert and fireworks (July 3)
  • Oktoberfest (October)
  • Holly Jolly Celebration (December)
  • Holiday Parade and Tree Lighting Ceremony (December)
  • New Year's Eve First Night Winchester celebration

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.

Old Town logo


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.



Alex Flanigan
Community Arts & Vitality Manager
Rouss City Hall
15 N. Cameron Street, Main Floor
Winchester, VA  22601
(540) 535-3661


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