Winchester
Trail Running Calendar near Winchester 2026-2027
Explore the top trail runs near Winchester for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A cross-country 5K and 10K at Talon Winery in Lexington with finisher awards and a wine drink ticket; under-21 participants receive the award but not the wine. The event includes wine sales, live music, and an after-party in the tasting room.
September 2026
GRC Cross Country Daniel Boone 5K is in Winchester, KY on September 5, 2026, with a down and back course from Lincoln and East Hickman to the country club. Entry fee is $30 and shirt registration is available until August 22.
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.
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.
An annual military fitness tribute at Queenslake Horse Farm in Georgetown, Kentucky honoring the 19 fallen heroes with a weight carrying challenge 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.
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