Winchester
Trail Running Calendar near Winchester 2026-2027
Explore the top trail runs near Winchester for 2026-2027! We've gathered 15 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
September 2026
A community 5K run or walk in Winchester, KY with a winding out-and-back course, event shirts for early registrants, and proceeds supporting the GRC Cross Country team.
A free cross country 5K in Georgetown KY with on-site shirt printing, concessions, and proceeds supporting a local running team's registration fees.
Community Pride Run at Coldstream Park with a chip timed 5K, 1 mile walk, virtual option, music and vendor tables supporting LGBTQ+ students and families.
The 30th annual Spoonbread Festival 5K in Berea KY offers a chip timed 5K on a flat paved trail, an untimed 1 mile fun walk, and a virtual 5K option with commemorative shirts and age group awards.
A charity 5K at Coldstream Park/Legacy Trail in Lexington on September 26, 2026 benefits NICU babies, with an in-person chip timed 5K, a kids 1/4 mile dash, and a virtual 5K option with mailed shirts.
Experience the natural beauty of Lexington at the Raven 10K Trail Run. Run or walk through grassy fields and primitive trails at the Raven Run Nature Sanctuary or join the event virtually from any location.
October 2026
Experience a scenic trail run through the Red River Gorge on a private looping course. This cup less half marathon supports local search and rescue teams while offering a festive atmosphere with medals and post race meals.
A free annual military fitness tribute at Queenslake Horse Farm honoring the 19 soldiers lost in the 1993 Battle of Mogadishu, featuring a memorial course and a full day music festival.
A second-annual fall 5K hosted by Gleaning Housing at Coldstream Park / Legacy Trail in Lexington, KY, with pumpkins for donors and snacks and drinks for all participants. Participants may bring or wear a pumpkin costume.
A 5K trail race at Silver Creek Bike Park in Berea KY on October 24 2026 with on course photography, water fill station, post race snacks and a cupless low waste policy.
November 2026
A 4 miles trail run and walk at Veterans Park in Lexington on November 14, 2026, over mostly hard-packed dirt trails with grassy and short paved sections. The race is chip timed, offers awards, hydration stops, and a virtual option with mailed shir..
March 2027
June 2027