• Spooktacular Featured

    Happening This Weekend

    Friday, October 24th: Christ Episcopal Church 3rd Annual Rummage Sale: The 3rd annual Christ Episcopal Church Rummage Sale is Friday, October 24th and...

  • Spooktacular Featured

    Old Town Winchester Spooktacular

    Things will get spooky on the Loudoun Street Pedestrian Mall on October 25th from 1pm to 4pm with the Old Town Winchester Spooktacular! Bring the fami...

  • Bright Box Winchester

    Bright Box Comedy: Kevin Meaney

    The Bright Box Theater’s Comedy series will be continuing on October 24th and 25th with performances by comedy legend Kevin Meaney. The shows ar...

  • Springfield Exit Featured

    Bluegrass in the Ballroom

    The George Washington Hotel will be having an evening of bluegrass on October 23rd. The event, which takes place in the GW’s Grand Ballroom, will feat...

  • mcKee's Featured

    New Business Opens in Old Town Winchester

    Old Town Winchester has gained another great business with the opening of mcKee’s, the Men’s Shop at Kimberly’s. Located in the same...

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 our new video to experience Old Town Winchester.


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