Trail Running calendar near Greenville 2026-2027

Two-day trail running event at Willenborg Woods near Charleston IL offering 5K, 8 miler, 16 miler, 50K and 100K on marked single-track trails.

Timed 6 and 12 hour endurance runs on a USATF certified 1.17 mile paved loop at Minnie Ha Ha Park, cupless and chip timed with aid station and finishers medals.

An annual open 5K at Jefferson Barracks Park in Saint Louis held alongside the Hancock Cross Country Invitational. The race welcomes all ages; registration opens August 1, 2026, with a $15 fee and closes on race day.

A 15K loop trail run and 15K ruck at Babler State Park with 1,350 feet of gain, a single unmanned water stop, and cup free sustainability policies.

Originally listed as a 5K at Washington Park in Springfield with registration closed and a $30 fee; a notice states the event has been renamed and moved to September 5th.

A two day trail racing weekend at Castlewood State Park with 10k, half marathon and 30k options, notable stairs, weekend challenge combinations, finisher gear and age group awards.

The City of the Sun 5K Trail Run will take place in Caseyville on Sunday 8 November 2026. You can run 5 kilometers.

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.

Celebrate Thanksgiving in St. Louis with this annual running event featuring multiple distances from a half marathon to a kids dash. Enjoy chip timing designer shirts and custom medals for all participants.

A trail running event in Wildwood, MO offering marathon, half marathon and 10K courses with cup free aid stations and an emphasis on sustainability.

A December trail race at Broemmelsiek Park offering 5 and 10 mile options with post-race music, beer for 21+, snacks and a bonfire.

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.

A winter trail series at Rockwoods Reservation near Glencoe, Missouri across three dates from Dec 19, 2026 to Feb 13, 2027. Events range from 4 miles and 8K up to a half marathon with finisher medals, shirts, chip timing and live tracking.

A 5K trail race at Cliff Cave County Park in St. Louis on January 1, 2027 featuring pavement sections and the Spring Valley Trail with about 272 feet of elevation gain.

A winter trail event at Creve Coeur Park with 1 mile, 5K, 10K and half marathon options, finishers receive a shirt and medal, and a portion of proceeds benefits the Crohn's and Colitis Foundation.

A winter trail series at Rockwoods Reservation near Glencoe, Missouri across three dates from Dec 19, 2026 to Feb 13, 2027. Events range from 4 miles and 8K up to a half marathon with finisher medals, shirts, chip timing and live tracking.

A Midwest winter ultramarathon in Missouri on January 16 and 17 2027 offering multiple trail distances from 20 miles to 100 miles, including a night 40 miler. The event is managed by PR Racing and alternates course direction by year.

A 15 km trail race at Indian Camp Creek Park on January 30, 2027, part of the Big River Trail Series, with post race barbecue, beer for 21 and over, and live music.

Timed trail event in Wildwood MO with 9 hour, 6 hour and 3 hour options on a 4.2 mile single track loop.

Winter trail event at Rockwoods Reservation in Glencoe Missouri offering a 5 Mile and a 13.1 Mile course. Organized by Rockinator Racing as the Stick Season finale with chip timing, aid stations, on course tracking and post race awards.