Chesterfield
Trail Running Calendar near Chesterfield 2026-2027
Explore the top trail runs near Chesterfield for 2026-2027! We've gathered 41 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Open 5K in Forest Park with a team competition, morning bib and shirt pickup, and a $15 registration fee; registration opens April 23 and closes September 12, 2026.
Free after dark social Halloween run in Chesterfield with treats, a free 4 Hands beer for runners 21 and older, raffle prizes and ghost stories.
October 2026
Experience technical trails and rolling hills at Greensfelder Park with distance options ranging from 8 miles to a 50K ultra. This cup free event features a repeating loop format through scenic Missouri woodlands.
A repeating loop backyard ultra at the New Town amphitheater in Saint Charles, Missouri, with a 4.17 mile runner loop and a 2.6 mile ruck division that includes weight minimums. Race proceeds support MSMDS research.
Free, beginner friendly guided trail running and hiking program in the St Louis metro from October 11 to December 20, 2026, with guided groups and ruckers welcome.
A fall community run in Washington, MO featuring a pumpkin-carrying 5K and a shorter Pumpkin Trail with music, snacks, games, and prizes.
Timed 6 hour and 12 hour runs on a USATF certified 1.17 mile paved loop through a mostly flat wooded park with Meramec River views.
Open 5K at Jefferson Barracks Park in Saint Louis as part of the Hancock XC Invitational, held on the meet's historic cross country course and open to a range of ages.
15K trail race at Babler State Park in Wildwood MO with an optional 15K ruck division requiring a 20 lb pack; field capped at 75, one unmanned water stop, cup free.
A race and recovery festival in Marthasville with chip-timed one-mile loops, aid every mile, recovery sessions, free camping and evening music.
A weekend trail event at Castlewood State Park offering 10K, half marathon and 30K options on October 31 and November 1, 2026, with challenge combinations and finisher awards.
Halloween-themed trail event in Legacy Park Cottleville offering 1 mile, 5K, 10K, a virtual option, and a kids dash with candy and a costume contest.
November 2026
Timed trail event on 11/28/2026 at Turkey Ridge in Wildwood with a 1.8 mile loop and 347 ft elevation gain per loop. Two time categories let runners complete as many loops as possible in 2 or 4 hours.
December 2026
A 7.8 mile trail run through Pere Marquette State Park in Grafton, IL on 12/12/2026 with packet pickup, pre race coffee and post race awards held in the park lodge. The event is planned to run in most weather conditions.