Trail Running calendar near Evanston 2026-2027

Experience a natural trail run at Saw Wee Kee Park featuring a soft path with twists and turns. Complete this event to earn a piece of the 2026 series medal and enjoy seasonal swag in a beautiful outdoor setting.

Timed trail races of 24, 12 and 6 hours take place on the dirt and grass loops of St. Patrick's County Park in South Bend. The course has three short asphalt crossings and proceeds benefit the ALS community.

Join the Jaimie Cox Memorial Run on October 17, 2026 in Roscoe, Illinois for a community 5K or 2 mile walk along the scenic Stone Bridge Trail. Family friendly with kids and virtual options, supporting the Jaimie Cox scholarship.

Trail races of about 5 and 10 miles through Veteran Acres and Sternes Woods in Crystal Lake, IL, with single-track trails, a cupless course, packet pickup options, and finisher medals for all distances.

Experience a haunted 5k trail run in Pingree Grove featuring live actors and animatronics. Stay for the bonfire and costume contest at this unique evening event.

A woodland ultra with 50K, 25K and 5-mile options run on a 5.5-mile single-track loop at Deer Grove Forest Preserve, featuring multiple stocked aid stations and explicit inclusion policies for race entries.

Celebrate Halloween and support animal shelters at this dog friendly 5k in Busse Woods. Enjoy a flat paved course with treats for both humans and leashed pets at the finish line.

A Halloween night run and walk through the Lake County Fairgrounds. The event includes a timed 5K and a non-timed 2K walk, costume prizes, and entry to a festive market. Bring a flashlight for the evening course.

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.

Embrace an autumn adventure at the Big Timber XC Challenge, a trail run featuring a famous creek crossing through the woods of Camp Big Timber. Choose between a 3-mile or 5-mile course on grass and gravel paths. All runners get a shirt and..

Experience the Bigfoot Half Trail Run at Stoney Run County Park. This two loop course features a mix of grass, dirt trails, and gravel with manual timing and unique raffle prizes for participants.

Experience the variable terrain of the historic Lemont Quarries at this multi distance trail festival featuring laps of single track and gravel paths ranging from 10K to 60K.

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.

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 dog friendly trail running event at Lake Geneva Ziplines and Adventures with a 4 mile loop, an 8 mile option, and a focus on Canicross. Awards are reserved for teams running with dogs and all finishers receive a small gift.

Experience a unique winter obstacle course in Lake Geneva featuring distances from 5K to 20K. Enjoy a festival atmosphere with fire pits and food trucks after conquering challenges designed for both fun and competitive athletes.

A winter trail ultrarun in Dousman, Wisconsin on Feb 27-28, 2027 offering 6, 12 and 24 hour solo or relay options, winter trail terrain, warming shelters, hot drinks and a post-race meal.

A trail event at The Forge Lemont Quarries on March 13, 2027 featuring a half and quarter marathon on wooded single and double-track trails with varied, technical terrain and one aid station for the half.