Trail Running calendar near Lake County 2026-2027

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.

Experience a 136 mile journey along the scenic Ice Age State Trail in Wisconsin. This endurance event features diverse terrain and comprehensive aid station support over a 55 hour timeframe.

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.

Experience the terrain of Michigan City with a series of loop based trail races ranging from 2 miles to 50k at Tryon Farm. Run through open fields and single track dirt trails to support the Tryon Farm Institute.

Experience natural dirt trails and scenic views at this Janesville event featuring a competitive 5k run and casual walk. Stay for the heritage celebration with food trucks and live music after you finish.

Run or walk along the tree lined Oak Leaf Trail before finishing at the Oktoberfest celebration in Glendale. This event features a 5k run and a 54 yard dash with post race refreshments and festival entry.

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.

Participate in a half marathon, 5K, or rucking event at Zachariah's Acres in Oconomowoc. Support nature based programs for children with special needs while exploring prairie trails and wildflowers.

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.

A flat, fast trail event along the Des Plaines River Trail in Lake County, Illinois, offering 50 mile, 50K, marathon and half marathon distances, manned aid stations, finisher medals, and a Boston qualifying marathon.

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.

A trail race in Crystal Lake, IL on Oct 17, 2026 offering roughly 5- and 10-mile single-track loops through Veteran Acres and Sternes Woods. The event is cup-less, includes a finisher medal, and has a 3 hour 30 minute cutoff.

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.

Woodland ultraruns on 5.5 mile loops at Deer Grove Forest Preserve offering 50K, 25K and a 5 miler with staffed aid stations and a focus on marked routes and inclusion.

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.