Welcome to downtown Winchester, Ky.


 Downtown Winchester is known for its authentic down-home charm and hospitality.  Just 17 miles from Lexington, downtown Winchester is a delightful blend of history, modern sophistication, and eclectic local characters.

We've earned recognition for our unique local flavors (beer cheese! Ale 8 One!), our super friendly community, and remarkable architecture. The heart of downtown is a multi-block national historic district and features the "High Side" of Main Street- one of the only elevated sidewalks in the Commonwealth!

Whether you're looking to explore our locally owned shops, restaurants and boutiques, take in a little history at the Bluegrass Heritage Museum or our cellphone walking tour, or catch a live show at The Leeds Center for the Arts there is something for everyone here.



Main Street Winchester is actively working to foster a creative and vibrant community through events, projects, economic development and innovative partnerships. 

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2010 promotional film made by Jason Epperson's Eppic Films for Winchester First (now known as Main Street Winchester).