Get Moving!

A healthy community is important to us!  Organizations from Tourism to the Bicycle Pedestrian Advisory Council to Clark Regional Medical Center to the Chamber of Commerce have been working on improving our walk-ability, access to alternative transportation and more.  Check out some fun ways to get moving in downtown Winchester!


main street mile

This downtown walking trail in Winchester is a great way to experience the remarkable architecture and great small businesses in downtown Winchester. It is one mile in length and  can be completed in about 20 minutes. Start on Depot Street or at The Bluegrass Heritage Museum.

The Main Street Mile was a group effort by Bluegrass Rails to Trails, Winchester First (now known as Main Street Winchester), the Clark County Activity Coalition, and the American Heart Association. It was dedicated in the summer of 2009.

Rick Beach Bicycle.jpg

bicycle alley tours

Explore downtown Winchester and surrounding neighborhoods via our historic alleyways. This gives a unique look at our community while avoiding the heavy traffic on the main roads.

Need a bike? We have you covered. 

More ambitious? Check out our Century Ride, Half-Century Ride and River Route - which all start on Main Street!



From fitness classes to martial arts to a stroll in the park - you can find it in downtown Winchester.  Learn more about our great downtown businesses like Bluegrass Budokai and The Barre: A Fitness Boutique below.