Trail Running calendar near Greenville 2026-2027

Test your limits on a scenic 20.35 mile loop near St Louis offering distances from 20 mile to 100 mile, plus a 100 mile team relay. Rugged single track, big climbs, indoor weekend lodging, cupless aid, and finisher swag make for a memorable..

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 15 km of single track trails at Castlewood State Park on Jan 31, 2026; expect hills, switchbacks, and scenic views. Join the 18th annual Castlewood Cup for a fun post race BBQ, beer, live music, and a sweatshirt and medal for finishe..

Run the 9th Annual 963 Beulah Challenge, a night trail race capped at 75 runners in Greensfelder County Park, Wildwood Missouri, over a rugged 4.2 mile single track loop by headlamp. Choose 12.6 miles 25.2 miles or 50K and help support Gate..

Join the Frozen Cock's Crow 5K at Willenborg Woods, a spirited trail run on technical singletrack with steep climbs and a stream crossing. Enjoy a family friendly, grassroots vibe and a fun post race celebration.

Tackle the 9th annual Bootlegger 10K this winter in Upper Creve Coeur Park, a scenic single track course with switchbacks and lakefront views. A 1.5 mile parade loop sorts the field before the trails and every finisher earns custom swag.

Double Chubb at West Tyson County Park serves trail lovers with 50K, 25K, 25K RUCK and 8M options. Expect rugged singletrack, full aid stations and a tough 25K ruck that requires carrying a minimum 20 pound pack for an extra endurance test.

Tackle scenic trails at Ozark Foothills Endurance Runs in Wildwood, MO, with races from a free kids mile to 100 miles over a weekend of trail challenges. The event is cup free and zero waste, so bring a mess kit.

Join the Green Park Viking Dash on April 18 in Saint Louis for a fun 5K and 1 mile run or walk starting at Green Park Lutheran School. Enjoy neighborhood and Grant's Trail scenery while supporting the school's Viking Village.

Take on a spring trail challenge at Queeny Park in Ballwin on May 2 2026 with 5K, 10K, 10K ruck and half marathon options on shaded gravel trails. Professional chip timing, medals, shirts and finish line photos make it a rewarding day for r..

Run the scenic 8K through Lincoln Memorial Garden on May 30 in Springfield, with wood chipped trails, bridges, and a Kids Fun Run around Cawley Meadow. Finishers get a shirt and wooden medallion, and the field is limited so register early.

Tackle rugged Ozark trails at Baby Shippey, a no frills summer trail race offering a half marathon and 10K at Beaumont Reservation. Expect rocks, steep climbs, great views, a custom race item for all finishers and awards for top runners.

Celebrate Independence Day at Freedom Run 2026 in Centennial Park, Springfield, with a 10K, 5K, and 1 Mile fun run. Chip timed courses start atop Centennial Hill, wind through scenic trails, and finish with breakfast, a shirt, and a medal.

Join the Madder Than A Wet Hen 5K in Charleston IL for a rugged forest trail run featuring a knee deep river crossing and a fierce climb up Billy Goat Hill. Reward yourself after the finish with pancakes and ice cream.

Tackle the Labor Day Slay at Queeny Park on August 29, 2026 with 5K, 10K, 10K Ruck or half marathon options on a marked trail loop that all start together. Expect chip timing, aid stations and a finisher medal.

Run fast rolling trails at Sand Creek in Decatur on Sept 12 and choose 4.4 or 7.6 miles for a lively trail challenge. Get a tech shirt and finisher medal while supporting the Special Operations Warrior Foundation.

Join the Miles for Marshall 5K trail run and walk on Saturday, September 26, 2026 at Patriot's Park in Greenville to support childhood cancer research and families. Run or walk scenic trails with community spirit and purpose.

Shake Your Trail Feather is a two day trail race at Willenborg Woods that winds single track trails, creek crossings and rolling climbs. Distances from 5K to 100K, full course support and a lively post race celebration.

Hit the roots and ridgelines at Babler Bongo, the first foot race at Babler State Park, featuring a lively 15K trail run and 15K ruck. Challenge yourself with a 20 lb ruck division, earn a custom patch, and support DOGS for our BRAVE.