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, Main Street Winchester 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. A National Program

Through our community directed projects, Main Street Winchester fosters a vibrant downtown community that celebrates its unique traditions, historic architecture, and the community’s spirit. Main Street Winchester is proud to be accredited by both Kentucky Main Street and Main Street America. Winchester’s program operates through City Hall. 

Community transformation through:

Economic Vitality
  • Build a diverse economic base.
  • Catalyze smart new investment.
  • Cultivate a strong entrepreneurship ecosystem.
  • Create an inviting, inclusive atmosphere.
  • Celebrate historic character.
  • Foster accessible people-centered public spaces.
  • Build leadership and strong organizational capacity.
  • Ensure broad community engagement.
  • Forge partnerships across sectors.
  • Market district’s defining assets.
  • Communicate unique features through storytelling.
  • Support “Buy Local” experience.

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 WSW, 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 be MSW. 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 MSW’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