Welcome to
Winchester, Kentucky

Experience the charm of a Kentucky gateway city. Seventeen miles from Lexington and the last exit before the Mountain Parkway, Winchester has a long history of commerce, tourism, and being a hometown. Explore locally owned shops. Taste wholly unique flavors. Experience the glow of a place that is unlike any other. No matter your interest, Winchester First can assist you in finding your place downtown.

Since 1793, Winchester, Kentucky has been the “Gateway to the Mountains” of Eastern, KY. With over 100 historic structures, Winchester’s downtown commercial district contains a collection of late 19th-century architecture. 

Beer Cheese Festival


What We Do

Community Powered. City Sponsored.

Through our community directed projects, Winchester First fosters a vibrant downtown community that celebrates its unique traditions, historic architecture, and the community’s spirit. Winchester First operates through City Hall. 

Doing Business Downtown

We are a community that helps each other succeed. Entrepreneurs, building owners, and community members can access a wealth of resources and opportunities. Investing in people is investing in downtown. Sharing our knowledge and capital is an investment in our community. 

For Building Owners
For Business Owners
For Community Members
Helpful Links

Business Testimonials

Frames on Main have benefited greatly from the hard work of Winchester First, from the promotions, guidance and support they have provided, we have survived and see constant improvements of downtown because of their efforts.

Brenda Salyers, Frames on Main

Arts on Main members appreciate the support shown by Winchester First. Without their support the October 2020 Street Fair would not have been possible or the success it was. All downtown businesses participated and appreciate MSW’s support. Kudos to MSW!!!!

Shelia McCord, Arts on Main

Arts On Main has been able to stay open throughout the pandemic because of Winchester First’s support of the 2020 Arts on Main Street Fair. We appreciate the support of our Winchester Art Guild sponsored business.

Elizabeth Chalfant, Arts on Main
Photo Gallery