Trail Running calendar near Chicago 2025-2026

Join Turkey Trails Greater Chicago at Hammel Woods on November 8 for family friendly 1 Mile, 5k, 10k and kids races plus a virtual option. Chip timed 5k and 10k finishers get designer shirts and medals while kids enjoy youth sized swag.

Join the River Rat Races at Kankakee River State Park on Sunday, November 9, 2025 for 10 mile, 10K and 5K runs plus a 5K walk along the scenic bike trail by Rock Creek bridge. Register by Nov 8 for $20; packet pickup and post race refreshme..

Run the MacNider cross country course in Schaumburg on Nov 9 at the Fast Track Cross Country Open, with separate men's and women's races over a scenic 3.05 mile looped grass course. A great fall test for solo racers and teams alike.

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 scenic trails at St Patrick's County Park on November 15, 2025 while supporting Rhyme & Reason Ministry. Distances from 1 mile to a half marathon offer fun for all abilities and chip timing ensures fast accurate results.

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 scenic trails at the Abominable Trail Race in Lake Geneva on November 15 with 5K, 15K and 30K distances plus team relay. Celebrate at Base Camp with live music, food trucks, local beer and cozy fire pits.

Join the Bigfoot Half Trail Run at Stoney Run County Park for a scenic two loop half marathon that benefits the park. Runners get a Bigfoot trucker hat and gloves and finishers earn a homemade wooden medal plus a raffle ticket.

Join the 58th Dowagiac All Trail Turkey Trot on November 23 for scenic trail 10K, 5K and a fun 1K kids run at Southwestern Michigan College. Enjoy chip timing, custom shirts for early registrants and festive post race vibes.

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.

Join the Winnetka Turkey Trot on Thanksgiving morning for a fun 5k on the Green Bay Trail with Family Trot and Speedy Trotters divisions and a rolling start. Festive vibes, kids get #1 medal and proceeds support local charities.

Join the Brooks Northeast XC Championships at Franklin Park on November 29 for fast 3K and 5K races for youth, high school and open runners. Enjoy medals, swag for early registrants and a shot at San Diego qualification.

Join the Brooks Midwest XC Championships on Nov 29, 2025 at UW Parkside in Kenosha, WI. Multiple races award medals and offer a shot to qualify for the Brooks XC Championships in San Diego.

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..

Start the year with the Frozen Feet 5k Trail Run at Creek Ridge County Park on January 3. Run two looped, rooty trails with a hill each, grab a cozy winter hat and gloves and enjoy a grassroots fun finish line vibe.

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.

Hit the trails at Red Mill County Park for the Cereal Killer 15k, a four loop trail race that mixes rugged fun with post race cereal and Deathwish Coffee. Limited edition long sleeve shirts and age group awards make for a memorable morning.

Tackle the middle race of the Fox Valley Winter Challenge Trail Series on Feb 21, 2026: an 8K at Oakhurst Forest Preserve with a steep sledding hill climb and twisty, rolling winter trails. Finishers get a custom medal and premium cold weat..