Trail Running calendar near Lemont 2026-2027

A grassroots loop ultra at Dixon Park District offering 25K, 50K, 100K and 100 mile options on a 7.85 mile mixed surface loop with two aid locations, crew and pacer policies, and finisher awards.

The Bloomingdale Trail 5K is an annual family-friendly running event in Chicago. It features a timed 5K race alongside shorter dashes for young runners. Registration is available for all three distances.

A timed 6- or 12-hour event on a 2 mile lakefront loop in Evanston with two aid stations, finishers' Hop Water and handcrafted awards, and permitted pacers.

A mixed-surface trail event at Tryon Farm in Michigan City featuring a 4 mile loop used for 4 mile, 8 mile, 25k and 50k distances plus a 2 mile fun run or walk, with a main station, a non-manned aid point, and parking across the street.

A community 5k run and walk hosted by the Lockport Fire Foundation on October 4, 2026 at Hassert Park in Lockport, IL. Entry includes a t-shirt and finisher medal for registered participants present on race day.

Join this community run and walk at Vollmer Road Grove Forest Preserve to support homeless school children. Participate in person on the paved 5K trail or join virtually to help provide essential school supplies for families in need.

Multiple endurance trail distances on a flat, crushed gravel section of the Des Plaines River Trail, starting and finishing at Half Day Forest Preserve in Lake County, Illinois. The marathon is a Boston Qualifier and the event runs each Oct..

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.

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.

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..

A half trail run at Stoney Run County Park on November 14, 2026, held over two loops across grass, pavement, gravel and single-track trails, with aid stations, on-site packet pick-up, a raffle and informal timing using popsicle-stick finish..

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.

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 four race winter trail series in Dixon, Illinois totaling 31 miles across four dates from December 2025 to March 2026. Distances range from 5K to 20K with series awards and age-category prizes.