Trail Running calendar near Glencoe 2025-2026

Castlewood Cup returns for its 18th year on January 31, 2026, at Castlewood State Park in Ballwin, Missouri. The 15-kilometer trail race courses through Castlewood’s renowned single-track, offering a scenic mix of hills, switchbacks, and oc..

Run under the stars on the 963 Beulah Challenge, a capped night trail loop in Greensfelder County Park. Choose 3, 6 or 9 hour timed runs on rugged singletrack and support local trail advocacy while enjoying small field camaraderie.

Spend Valentine season on Forest City singletrack at Maramec Spring Park with a mid February trail run. Options from 5K to 100 mile plus relays and camping invite runners of every level to enjoy scenic river side trails.

Run until you stand alone at Queeny Backyard Ultra, a last runner standing trail event on a scenic 4.19 mile loop at Queeny Park. The 2026 Silver Ticket edition awards the winner a spot at the World Team Competition at Big's.

The Schon Park 3/6/9 Endurance Runs, hosted by Ultra Bound Coaching, take place in Glen Carbon, Illinois. This timed event offers three durations: 3, 6, and 9 hours, where participants run loops on a 1.5-mile paved course featuring rolling..

Join the Double Chubb trail races at West Tyson County Park on March 28, 2026 with distances from 8 miles to 50 kilometers. New this year is a 25K RUCK where runners carry 20 pounds for a tough, rewarding trail challenge.

Join a multi distance trail weekend in Wildwood, Missouri April 10 to 12 2026 featuring ultras and fun runs for every level. Part of the 50K Mashup series, the race embraces a cup free, zero waste approach so bring a personal mess kit.

Tackle scenic, continuously hilly single track through Mark Twain National Forest at Berryman Campground with marathon (one loop) or 50 mile (two loops) options. Expect rocky roots, stream crossings and a friendly post race barbecue.

Baby Shippey is a rugged trail run at Beaumont Reservation featuring rocky climbs, steep descents and two challenging distances. Field limited to 150 runners, cupless event with custom swag and a post race gathering.