Nicholasville
Trail Running Calendar near Nicholasville 2026-2027
Explore the top trail runs near Nicholasville 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.
September 2026
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.
A limited-field trail 10K at Raven Run Nature Sanctuary with a virtual option, commemorative shirts, and awards for top overall and age-group finishers.
October 2026
A 1.8-mile military-style obstacle challenge at Queenslake Horse Farm on Oct 3, 2026 honoring the 19 fallen with memorial stations and a lakeside 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.
A no-contact Zombie 5K paired with an Autumn Fun Fest featuring a vendor fair, costume contest, games, and a pet supply drive to benefit local animal care.
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..
A 5K Run and Ruck on November 14, 2026 in Wilmore, Kentucky where 100% of proceeds support Thomson-Hood Veterans Center.
A two mile fun run in Huntertown Community Interpretive Park run as two laps on a mowed grass trail, with food trucks after the event and a T‑shirt deadline of Nov 1.
April 2027
A timed endurance event in Parksville, Kentucky with 3, 6, 12 and 24 hour running and ruck options, relays, on-site camping, and a full aid station at the start/finish.
May 2027
Test your strategy and endurance in a two hour adventure race featuring eighteen unique challenges like ziplining and climbing across a five hundred acre Kentucky farm.
September 2027
Chip timed 5K at Kentucky Horse Park on the Hunter Pace turf and cross country course with awards, shirts, ribbons, photos and proceeds to the Kentucky Horse Council.