• Now Accepting First Friday Applications!

    Calling all artists! Do you want the chance to showcase, demonstrate, or sell your work for free on the Pedestrian Mall? Do you want to meet other art...

  • Chocolate Escape

    Get a little extra sweetness in your life with our 10th annual Chocolate Escape! Join us in Old Town on February 4 from 2-5pm for specials, discounts,...

  • Restaurant Week 2023

    Restaurant Week returns February 20-25! The 9th Annual Winchester Restaurant Week, presented by the Winchester Main Street Foundation, provides an opp...

  • 2023 Special Events Calendar Announced!

    2023, we’re ready for you! The Main Street program of Old Town Winchester is happy to present the 2023 year-at-a-glance calendar for special eve...

Welcome To Old Town Winchester, Virginia!

Whether you come here to visit, live, work, or invest, you’ll find Old Town to be a rare gem of a place.

Discover charming shops, delicious restaurants, centuries-old architecture, numerous historical landmarks, and museums waiting to be explored. Old Town Winchester offers convenience, charm, and a warm welcome to all. Discover Old Town Winchester and join us at downtown Events. 

Check out this video profile to experience Old Town Winchester.

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