Trail Running calendar near Evanston 2026-2027

A trail event at Camp Big Timber on November 8, 2026 featuring 3- and 5-mile perimeter loops plus a kids fun run. The course includes grass, gravel, a creek crossing and a post-race pancake breakfast for all participants.

A two-loop trail run at Stoney Run County Park on November 14, 2026, over mixed surfaces with on-course aid stations. Packet pick-up includes a raffle and memorabilia sales, with proceeds benefiting the park.

Late November trail festival in Lemont IL offering 10K, 20K, 30K and 60K on single and double track and gravel around historic quarries and the I&M Canal. Courses start and finish at The Forge and use lap formats.

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.

The St. Joe Valley Happy Trail Run will take place in Roseland from Saturday 14 November 2026 to Monday 16 November 2026. You can run between 5 and 13 miles.

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 Canicross focused running event at Lake Geneva Ziplines and Adventures offering a 4 mile loop with an option to do two loops for 8 miles. Dogs may run hands free in Canicross or on a y shaped harness with a handheld leash.

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.

A winter timed ultra in Dousman, Wisconsin offering 6, 12, and 24 hour options for solo runners or relay teams of up to four, set in winter woods and on a frozen lake with warming shelters, hot drinks, a meal, and finisher items included.

Early-season trail races at The Forge in Lemont, Illinois, on wooded single and double track trails with mud, roots and gravel. Distances offered are 13.1 miles and 6.5 miles with technical singletrack sections.

Trail races of 30k, 50k and 50 mile are scheduled March 13, 2027 at Sunset Hill Farm County Park in Valparaiso, IN, with a 16 hour time limit, one aid station, and finish awards including belt buckles and a wooden medal.

Trailbreaker returns to Waukesha on April 4, 2027 with races from a 1K kids run to a full marathon, plus ruck options and a walk. Proceeds support the Park Foundation of Waukesha and local parks and recreation.

A looped trail event at Deer Grove Forest Preserve west in Palatine, IL offering 5.5 mile, 25K, 50K and 50 mile distances. The course is mostly wide and not technical with one aid station at the start and playful on course shenanigans.

A family-friendly trail event at St. Patrick's County Park offering 50k, marathon, half marathon and 10k distances with marked courses and chip timing by Watts My Time.

Flat out and back half marathon and 10 km on the limestone Great Western Trail, hosted by Fox River Trail Runners. Registration fees and donations support three local mental health charities.

Trail marathon and 10 mile on the Sag Valley Trail at Cap Sauers Nature Preserve in Palos Hills, IL, with wide horsetrail, notable elevation gain, and staffed aid stations along the routes.