Winchester Main Street Foundation has announced February 21-26 as the dates for 2022 Winchester Restaurant Week! They are currently accepting sign-ups...

2022 Old Town Creative Communities Partnership Grant The Old Town Advancement Commission values the role of art in the community and seeks to foster a...

Old Town Winchester kicks off the 2022 event season with the return of an annual favorite, Chocolate Escape! Join us on Saturday, February 5 for a dec...

Here comes Santa Claus, here comes Santa Claus, right down…to Old Town Winchester! Follow Santa down from a morning of holiday fun at the War Me...

We’ve got a holly jolly mystery on our hands, folks! Ever since we put our tree up, more decorations just keep springing up overnight. There’s lights ...

Save the date! Windependent Weekend is coming Nov. 26 & 27! With the holidays upon us, there’s never been a more important time to shop local. Whe...

Get in the Old Town Spirit with Winchester’s new DORA license–a new way to sip, shop, and stroll your way through the heart of Old Town! R...

Are you a musician, artist, or performer who wants to show off your skills on the Loudoun Street Mall? Check out this quick guide we’ve put toge...

As summer heats up, crowds start to grow, and events start to return to Old Town, we need enthusiastic volunteers now more than ever! Whether your ski...

Come play while you can! The Splash Pad closes for the season on October 22! Come cool off at the Old Town Winchester Splash Pad located on the south ...