Trail Running calendar near Mount Prospect 2026-2027

A Halloween-themed trail event in Pingree Grove, IL on October 23, 2026 with multiple 5 km heats, haunted sets and animatronics, plus a costume contest, bonfire and food; spectator fee $10, free parking.

A trail ultramarathon at Red Gate Woods near Chicago offering 25K and 50K on a clockwise single track loop of about 5.5 miles, with staffed aid stations, course maps, and no pacers allowed.

Howloween 5K in Schaumburg is a chip timed 5K run or walk at Busse Woods that supports animal shelters. Pets may join without registration and a virtual participation option is available.

A Halloween themed nighttime run and walk at Lake County Fairgrounds in Crown Point on October 30, 2026. The event features a 5K and a non timed shorter course, costume prizes, awards, and entry to the Hometown Hocus Pocus Market.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding forest projects.

Trail runs and a walking option use a rolling park course that starts at the southwest corner and returns through woods, service road, and open sections with occasional rough footing and visible seasonal foliage.

Trail running at Camp Big Timber in Elgin, IL on November 8, 2026, featuring 3 and 5 mile perimeter courses with a creek crossing. A kids fun run and a pancake breakfast are included, and proceeds support local youth organizations.

Bigfoot Half Trail Run at Stoney Run County Park in Hebron IN is a two-loop trail race over mixed surfaces with aid stations, packet pickup, raffle items for park fundraising and manual finishing with numbered popsicle sticks.

A trail festival in Lemont on November 14, 2026, offering 10K, 20K, 30K and 60K on single and double-track trails and gravel around the Lemont Quarries and I&M Canal, with multi-lap courses and variable terrain.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

Bucks & Does 13.1 Pointer is a multi-distance running, walking, and ruck event at Nashotah Park on 11/14/2026. Distances range from a youth Bambi Run to a 13.1 Pointer, and every finisher receives a wooden finisher medal.

A community Turkey Trot through Atwood Park near 5k with chipped timing, common trail obstacles and door prizes. No GPS or timing devices are allowed and donations are collected for local causes.

A Thanksgiving 5K on the Green Bay Trail at Winnetka Train Station featuring rolling start waves, a family division, packet pickup before race day, post-race refreshments, and support for local charities.

A 2.5 mile chip timed cross country Turkey Trot on Thanksgiving morning in Orland Park, with long sleeve race shirts, a post race raffle, and prize turkeys for top finishers.

Regional cross country championships in Kenosha, WI on November 28, 2026, featuring multiple 5K races and a 3K youth event. Top finishers in the championship race can qualify for the Brooks XC National Championships in San Diego.

A public cross country race in Evanston with three all-grass loops, team and individual scoring, included long-sleeve race shirt, and a post-race awards cookout; entry fees vary by registration date.

A canicross-focused event at Lake Geneva with 4-mile loops (option to double for 8 miles), technical single-track trails, dog-specific awards, on-course hydration refills, and rules to protect the venue and wildlife.

A winter trail series at Dick Young Forest Preserve in Batavia featuring 5K, 8K, and 10K races on separate dates in early 2027, with combined registration and a series swag reward program.

A winter obstacle race at Lake Geneva offering 5K, 10K, a 20K Yeti Challenge, a kids course, team packs and a virtual option. Fun heats allow skipping obstacles while the Elite division requires full obstacle completion for podiums.