If you are looking for races in Winchester, Kentucky, you have come to the right place. Winchester has a growing running scene with 5 races listed in our directory, including 0 upcoming events in 2026. Whether you are lacing up for your first 5K or chasing a new personal record, there is something here for every runner.
Upcoming Races in Winchester, Kentucky
Here is a look at the top upcoming races in Winchester this year. We update our listings weekly so you always have the most current information.
10,000 Meter on Van Meter
Date: September 26, 2026
Join us at the Kroger Youth Soccer Complex on Van Meter Road in Winchester for this 10K celebration starting at 8:00 am, where you’ll compete for cash prizes across multiple categories including overall winners and age-group competitors (ranging from 11 and under through 70+). Read full details →
GRC Cross Country Daniel Boone 5K Honoring David Borden
Date: September 5, 2026
Distance: 5K
Head out Saturday, September 5th at 8:30am for this down-and-back 5K in Winchester, KY that starts at the corner of Lincoln and East Hickman, loops around the country club, and honors David Borden. Read full details →
Beer Cheese 5K
Date: June 13, 2026
Distance: 5K
Get ready to run a scenic down-and-back route from Heritage Park to Legacy Grove in Winchester, KY on Saturday, June 13th at 8:30amall for just $30! Sign up by May 31st to guarantee your race shirt, though late registrations are accepted through race day. Read full details →
Alexis Thompson Memorial 5K/10K
Date: June 6, 2026
Distance: 10K
Join the running community in Winchester, KY on June 6, 2026, for the 10th Annual Alexis Thompson Memorial 5K/10Ka decade-long celebration honoring Alexis’ legacy and commitment to community service. Read full details →
2026 Run for the Paws 5k Run/Walk
Date: May 16, 2026
Distance: 5K
Get ready to lace up on May 16th for this community-focused 5K in Winchester, KY, where you’ll support the Clark County Animal Shelter while logging your 3.1 mileswhether you choose to run, walk, or bring your pup along! Read full details →
Why Run in Winchester?
Running events in Winchester offer a mix of community fun runs, charity 5Ks, and competitive road races throughout the year. The local running community is active and welcoming to runners of all levels — from first-timers to seasoned racers. Many of these events benefit local charities and organizations, making race day about more than just your finish time.
Find More Races in Kentucky
Winchester is just one part of a thriving Kentucky running scene. If you want to explore more events across the state, check out our full race listings for Kentucky — we track every upcoming running event from 1 mile fun runs to full marathons.
Get Ready to Race
Found a race you want to run? The next step is making sure you are properly trained for it. Whether you are a first-timer aiming to finish or a veteran chasing a PR, having the right training plan makes all the difference.
Take our free 3-question training plan quiz and get matched to the right plan for your fitness level in under a minute. We will send it straight to your inbox so you can start training today.
Good luck out there — see you at the finish line in Winchester!
