Trail Running calendar near Greenville 2025-2026

Run the 5th annual Wild in the Woods Trail Race at Broemmelsiek Park on Saturday, December 6, 2025, featuring scenic 5 and 10 mile trail loops and points toward the Big River Trail Series. After the finish enjoy a fire pit, live music, snac..

Run the Wildwood Trail Marathon or Half on December 6, 2025 in Wildwood Missouri, featuring scenic, technical single track through parks and riverfront. Expect a finisher medal, catered post race lunch, and race day registration.

Join the 36th Pere Marquette Endurance Trail Run on December 13, 2025 in Grafton, Illinois. This 7.8 mile route winds through Pere Marquette State Park with hilly, scenic terrain plus pre race coffee, packet pickup in the lodge, and post ra..

Kick off the new year with Doomsday 5K, a beginner friendly trail run at Cliff Cave County Park in Saint Louis on January 1. Tackle rolling hills, earn a custom finisher medal and enjoy post race coffee at this eco conscious event.

Brave winter trails at Creve Coeur Park on January 4, 2026 with the Shivery Icy Trail Run offering 1 mile to half marathon options plus virtual entries. Enjoy a finisher hat, hot drinks, live music and support Crohn and Colitis research.

Shippey Endurance Runs is a winter trail ultra at Beaumont Scout Reservation offering 20 miles up to 100 miles, a 100k and a five person 100 mile relay over rugged single track and jeep roads. Indoor aid stations and on site camping.

Run winter trails at the FROZEN STICK Trail Run in Glencoe, Missouri, offering 5 mile and 13.1 mile courses through Bluffview, Rock Hollow and Zombie Trails. Finish at LaSalle Middle School for indoor post race festivities and finisher swag..

Tackle a scenic 15 km trail through Castlewood State Park on single track trails with challenging climbs, fast descents and switchbacks. Celebrate after the race with BBQ, beer and live music while earning Big River Trail Series points.

Run the 9th annual 963 Beulah Challenge, a 75 runner night trail event at Greensfelder County Park with timed multi hour loops on technical single track. Proceeds support Gateway Off Road Cyclists and a solid headlamp is recommended.

Run the Frozen Cock's Crow 5K in Willenborg Woods on Feb 14, 2026, a rugged winter trail with steep climbs, a stream crossing and scenic singletrack. Join the trail community afterward for food, fun and warmth.

Take on scenic West Tyson County Park with options from an 8 mile fun run to a challenging 50K, plus a new 25K ruck class. Loop trails and well stocked aid stations make the Double Chubb a supported, adventurous day on the dirt.

Ozark Foothills Endurance Runs returns to Wildwood Missouri April 10 to 12 2026 with trail options from a free 1 mile Kids Fun Run to a 100 mile ultra. Weekend highlights include a night 50K and a 25K ruck, with cup free low waste race prac..

Run the Green Park Viking Dash on April 18, 2026 with a family friendly 5K or 1 Mile Fun Run along Grant's Trail and nearby neighborhoods. Medals for all, proceeds benefit Green Park Lutheran School, and shirts for early registrants.

Join the Spring Sprung at Queeny Park for 5K, 10K, 10K Ruck and half marathon on scenic paved trails with tunnel and bridge crossings. Chip timing, finisher medals, race shirt and snacks support Rockwoods School District Cross Country.

Enjoy a scenic 8K through Lincoln Memorial Garden in Springfield on May 30, 2026, weaving lakefront paths and prairie trails. Kids fun runs, post race food, and a wooden finisher medallion make this intimate event limited to 300 runners.

Tackle rugged, boulder strewn trails and steep climbs at Baby Shippey, a cupless summer trail race at Beaumont Reservation. Limited to 150 runners, pick a half marathon or 10K for a raw, adventurous day on primitive singletrack.

Take on Madder Than A Wet Hen, a rugged 5K trail race at Willenborg Woods in Charleston on July 25, 2026, with river crossings, steep climbs and roughly 1,100 feet of gain. Field limited to 125, with post race pancakes and ice cream.

Join the Labor Day Slay on Saturday, August 29, 2026 at Queeny Park in St Louis for 5k, 10k, half marathon and 10K Ruck on fully marked trail loops. Expect chip timing, finisher medals, swag and race day packet pickup.

Hit the fast rolling Sand Creek trails near Decatur with 4.4 or 7.6 mile options, in person or virtual. Enjoy a technical long sleeve shirt, finisher medal and snacks while supporting the Special Operations Warrior Foundation.

Join the Miles for Marshall 5K trail run and walk at Patriot's Park in Greenville to support childhood cancer efforts. Enjoy scenic trails, community spirit, and a meaningful cause this September 26, 2026.