Trail Running calendar near Chicago 2026-2027

Experience the natural beauty of Wolf Road Woods with 3, 6, or 9 mile trail runs on a scenic loop course. Enjoy a relaxed atmosphere featuring off road terrain and post race celebrations in the heart of the Palos Trail System.

This cross country run on July 4th in Williams Bay offers a 5K on grass trails through the Kishwauketoe Nature Conservancy. A kids' quarter-mile event is also available. Registration is online only, with awards for top age-group finishers.

H-F Beast Obstacle Course Dash in Homewood, IL on July 12, 2026 features two age categories with obstacle runs. The event awards finisher medals and t shirts and includes an optional prep course in June.

Oakadoke Trail Runs features tree-covered single-track, switchbacks and creek crossings on looped 4, 9 and 18 mile courses near Valparaiso, IN, with frequent aid stations and a cupless race format.

A community cross country race in Mount Prospect on August 9, 2026 offering 1, 2 and 3 mile distances to raise funds for the Little Giraffe Foundation and research into premature babies.

Experience a Scottish themed obstacle course race in Pingree Grove featuring 15k, 5k, and family 3k distances. Challenges include classic rigs and unique tasks like archery and caber carries in a Highland setting.

Run a chip-timed 5K or join a scavenger hunt 3K walk at St. Patrick's County Park. Everyone gets a handcrafted medallion, plus there's an egg bake breakfast and door prizes. Leashed dogs are welcome on the walk.

Run the Rails in Elburn, Illinois on August 22, 2026 features a 1-mile fun run plus 4- and 7-mile courses that start and finish at Prairie Park. The routes cross the Union Pacific West rail line and benefit the Elburn Parks Commission.

The Summer Trail Classic offers three distances on the single-track trails of Paul Douglas Forest Preserve. It's the third race in a yearly trail series, with proceeds supporting local trail maintenance. Participants receive a running vest..

A 10 hour endurance run at Bluhm County Park on August 29, 2026, using a 4 to 4.1 mile loop completed on an hourly clock. Runners earn chips after four loops to trade for prizes and receive a limited edition shirt and wooden medal.

A USATF-certified half marathon and 10K through Danada Forest Preserve on crushed limestone trails, finishing near the horse track. Both distances award finisher medals, with chip timing, pacers, shuttle parking, and on-course water station..

A three day trail event at Rock Cut State Park featuring a night 10 km plus 25 km and 50 km races, with single race entries and Triple Crown series options that award commemorative spike prizes to finishers.

A timed running event on an about 1 mile paved loop in a 58 acre Chicago park, offering 3 hour, 6 hour, and 12 hour formats plus relay options and hourly on course challenges.

This obstacle course race at Indiana Dunes National Park offers three distances, including a K9 event. The course features diverse terrains inspired by military landscapes. It's open to participants aged 13 and up.

A multi-division obstacle course event at The Cliffs park featuring 5K and 10K courses, a ruck division, a multi-lap Bearded Challenge, and a kid's course. Finishers receive a shirt, medal and professional action photos.

A loop-based running event at Limestone Park offering 8 hour and 4 hour races on a 1.65 mile course with mixed crushed limestone and asphalt terrain. Scoring is by completed loops and proceeds support local organizations.

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.