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're celebrated 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.  It features the "High Side" of Main Street- one of the only elevated sidewalks in the Commonwealth!

Explore our locally owned shops, restaurants and boutiques. Take in a little history at the Bluegrass Heritage Museum or on 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 works to foster a vibrant community. Our activities include events, projects, economic development initiatives and innovative partnerships.

Learn More →

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