Trail Running calendar near Winnetka 2026-2027

Tough Mudder Chicago on August 29, 2026 at Rockford International Airport offers 5K, 15K and an eight hour Infinity format across fields, trails and creek crossings, with Mudder Village, finisher items, and group and volunteer options.

Take on a scenic one mile loop at Lapham Peak with 24, 12, and 6 hour timed options or set distance goals like a marathon or 50 miles. Lighted night laps, a stocked aid station, and a welcoming club vibe make every lap count.

A chip timed half marathon and 10K through the crushed limestone trails of Danada Forest Preserve near Wheaton, IL, with USATF certified courses, finisher medals, pacers, shuttle parking, a virtual option and live participant tracking.

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 rugged obstacle course race featuring hills, cliffs, and wooded trails in Marseilles. Choose from competitive 10K heats, multi lap challenges, or non competitive fun runs and rucking divisions for all interest levels.

Experience ten miles of hills and winding trails through the Byron Forest Preserve and Nardi Equine Prairie. This cup free race features cash prizes and a post race celebration with pizza at Hairy Cow Brewing Company.

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.