• Windependent Weekend

    It’s the most wonderful time of the year! The holiday season is upon us, and there’s no better place to do your most important shopping th...

  • HalloWinchester

    HalloWinchester is a celebration of all the incredible autumn and Halloween events happening throughout October in Old Town Winchester! Whether you...

  • Fiddles & Fifths

    FIDDLES & FIFTHS BLUEGRASS & BOURBON FESTIVAL Back for another year, it’s Fiddles & Fifths in Old Town Winchester! Get ready for an ...

  • First Friday

    First Friday is back this week and the weather couldn’t be better! So let’s take a moment to recap what to expect and what you can look fo...

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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