• 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...

  • KidzFest!

    KidzFest is just around the corner! Join us in Old Town Winchester on Saturday, May 13 between 12-5PM to experience a fun, free day out for the whole ...

  • Apple Blossom Festival Information

    It’s Apple Blossom Time once again! As we gear up to celebrate the Bloom, we here in Old Town want to make sure you have the safest, smoothest, ...

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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