Trail Running Calendar Illinois 2025-2026

Run single track trails at Beaver Dam State Park on Nov 1 in the MCDD Beaver Dam Dash with 5K, 10K and a 1 mile fun run. Proceeds benefit the Macoupin Center for Developmentally Disabled to support life skills and social programs for adults..

Join the 27th annual Rattlesnake Master Run for the Prairie in Urbana, Illinois to support Grand Prairie Friends with 5K and 10K trail and park courses plus virtual options. Expect medals, music, and a celebration of local prairies.

Run by moonlight to support Unity Christian cross country with 6k and 2k on an all grass course lit by a Super Moon and 200 solar lights. Enjoy unique awards, soup and sandwiches and be sure to wear lights for a fun glowing night run.

Turkey Trails - Greater Chicago is a Thanksgiving-themed running event in Shorewood, Illinois, held at Hammel Woods Route 59 Access (554 Brook Forest Ave). It offers in-person distances of 1 mile, 5k, 10k, a Kid’s Dash, plus a Virtual Race..

Tunnel Hill 100 in Vienna Illinois offers 100 mile, 100 km, 50 mile and marathon on a certified USATF and IAU course. The 50 mile serves as the USATF 50 Mile Road Championships and starts and finishes at Vienna City Park with aid.

Tackle rugged trails and a fun creek crossing at the Big Timber XC Challenge in Elgin. Choose 3 mile, 5 mile or a kids fun run, enjoy pancakes and a finisher woodallion, and support local youth organizations.

Run the Fast Track Cross Country Open in Schaumburg on Sunday November 9 with separate men and women races on a scenic 3.05 mile looped grass course. Open to all ages and abilities, teams are welcome.

Run the River Rat Races on Sunday November 9 2025 at Kankakee River State Park in Bourbonnais, with 10 mile, 10K, 5K and 5K walk options on a scenic bike trail. Packet pickup at Rock Creek pavilion and post race refreshments and awards for..

Run the scenic Lemont quarries and I&M Canal at The Forge Trail Run Festival, with distances from 10K to 60K for every trail runner. Expect wooded single and double track, some technical sections, and a friendly festival vibe with limited e..

Run a scenic wooded 5K loop at Ballard Nature Center on November 16, 2025, choosing a one lap 5K or the 4 Hour endurance challenge to rack up as many laps as you can. Try the Oscar Mike Ruck SACK for weighted ruck awards and a finisher meda..

Run the 53rd Rockford Road Runners Thanksgiving Turkey Trot on Nov 27 for a rugged 5k trail at Atwood Park with hills, rocks and roots. Enjoy holiday fun while supporting the Rock River Valley Food Pantry and local youth programs.

Join the Orland Park Turkey Trot for a chip timed 2.5 mile cross country run through woods and paved paths around Village Hall. All participants get a long sleeve dri fit shirt and winners take home prize turkeys.

Chicago Gaelic Park Carraig Challenge The event is a cross country running and walking event at Chicago Gaelic Park / Carraig Irish Pub in Oak Forest, Illinois, on Sunday, November 30, 2025. Two course options are offered: 5K run 1.5 mile..

Hit the trails at Timber Pointe for a scenic cross country style 8K, 4K or multi lap challenge with possible deer and eagle sightings. Partial proceeds benefit the nature center and finishers enjoy post race food and warm company.

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..

Start 2026 at the Siberian Express, a 7.45 mile winter trail run at Kickapoo State Recreation Area on January 3. Expect steep climbs and creek crossings, carry your own hydration, and warm up at a friendly post race gathering.

Take on the 50K MASHUP SLAM, a Midwest trail series that spans eight scenic events and rewards runners who finish five races with a special finisher buckle. Top series placers earn awards at the final G.O.A.T.z or Miner 49'er event.

Challenge winter single track trails at Veteran Acres and Sterne's Woods in Crystal Lake on a triple black diamond course offering 50K, 10K and relays. The 50K is five laps of a 10K loop with a warm Gnome Depot serving hot food and coffee.

Tackle winter trails in the Fox Valley with a three part Challenge Series featuring a 5K in Batavia, 8K in Aurora and 10K in St Charles across Jan to Mar. Register single or as a bundle and earn upgraded swag for multiple races.

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.