Trail Running calendar near Cottleville 2026-2027

Tom Sawyer's Trial by Trail is a 10K trail race in Hannibal, Missouri on October 17, 2026, using single track, dirt and paved trails. The Year Two edition includes masters divisions, cash prizes, age group awards and a three hour cutoff.

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 15 kilometer trail event at Dr. Edmund A. Babler Memorial State Park on October 24, 2026, offering both a foot race and a ruck division. Ruck participants must carry at least 20 lbs and receive a custom rucking patch.

Trail races at Frenchman’s Bluff on October 25, 2026 offer an 8 Mile and a Half Marathon with bluff views, creek crossings and varied single track and fire road terrain. Entry is limited to 400 and finishers receive a long sleeve shirt and..

A point-to-point trail ultramarathon near Steelville, Missouri covering about 100 miles of single-track through Mark Twain National Forest, with roughly 12,000 feet of gain, 13 aid stations, crew access, drop bags, and pacer options.

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.

An annual 5K trail fundraiser at Cahokia Mounds State Historic Site on November 8, 2026. The 3.1 mile course runs over paved, wooded and grassy terrain and supports community outreach and educational programs.

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 team focused winter trekking event at Johnson Shut-Ins State Park from December 4 to 6, 2026. Three courses range from a wheelchair accessible 4 mile walk to multi day 40 mile and 17 mile treks, honoring Korean War service members.

Trail race in Wildwood, Missouri offering Marathon, Half Marathon and 10K on mixed single track, gravel and paved surfaces with notable elevation gain. Cup free event with manned aid stations and race day registration options.

Wild in the Woods is a trail race at Broemmelsiek Park on December 5, 2026, with 5 mile and 10 mile loop options. The event includes live music, a complimentary beer for ages 21 and over, 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, MO on January 1, 2027. The course mixes pavement and the all dirt Spring Valley Trail with rolling hills and roots, and follows a cup free zero waste policy.

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.

Castlewood Cup is a *15 km* trail race at Indian Camp Creek Park on January 30, 2027, featuring a post-race BBQ, beer for those 21 and over, live music weather permitting, finisher medal and photos; it is part of the Big River Trail Series.

Trail event at Maramec Spring Park in February 2027 offering distances from 5K to 100 miles, on two named park trails with aid, camping, and awards including buckles for the longest distances.