Trail Running calendar near Libertyville 2026-2027

Trail races of approximately 4, 9.5 and 13 miles at Paul Douglas Forest Preserve on August 23, 2026. Part of the Dick Pond Athletics Darn Tough Trail Race Series with awards, raffle prizes, and proceeds benefiting Chicago Area Mountain Bike..

Tough Mudder Chicago on August 29, 2026 at Richardson Adventure Farm features 5K and 15K obstacle runs, an 8-hour Infinity lap format, Mudder Village festival amenities, and finisher medals, shirts, headbands and drinks.

A timed 10-hour endurance run at Bluhm County Park on August 29, 2026 where runners repeat a 4 to 4.1 mile trail loop with hourly cutoffs, chip-based prizes, a limited-edition shirt, and a wooden medal.

A continuous loop trail race at Half Day Forest Preserve offering 3.1 mile laps for 40 or 50 mile distances, with a 12 hour cutoff and fully stocked aid at each lap. Crew access and personal staging areas are provided.

Loop based trail event at Half Day Forest Preserve near Vernon Hills, Illinois. Runners complete one 5K loop at a time on mostly flat crushed limestone, gravel and natural trails with centralized aid and crew access.

A technical trail event at Franklin Creek State Natural Area in Franklin Grove, IL, offering 5K and 10K courses with multiple creek crossings and about 100 ft elevation gain per mile. Runners, walkers, and ruckers take part and proceeds sup..

Timed 24 hour, 12 hour and 6 hour runs take place at Lapham Peak State Park on September 5 and 6, 2026, on a one mile loop with night lighting and chip timing. The event includes a cupless aid station and a Distance division.

A half marathon and 10k at Danada Forest Preserve in Wheaton on crushed limestone trails, finishing around the horse race track. USATF certified courses with chip timing, pacers, finisher medals, shuttle parking and packet mailing options.

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 urban ultra at Horner Park with 3, 6 and 12 hour options on a short paved loop, hourly challenges, a single aid station, and two or four person relay teams.

An obstacle course race at Indiana Dunes National Park on September 13, 2026, featuring 10k, 5K and a K9 3.1-mile event. The course uses varied landscapes to reflect terrains associated with military service.

Midwest OCR in Marseilles, Illinois features 5K and 10K obstacle courses, ruck options, a kid's loop, and a multi-lap Bearded Challenge, with finisher shirts, medals, and professional photos included; elite divisions award podiums and cash..

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.

A 136 mile point to point on the Ice Age State Trail through the Southern Kettle Moraine, with varied trail surfaces, nine staffed aid stations and full on-course support over an approximate 55 hour time limit.

A multi-distance running and walking event at Moraine Hills State Park offering 5K, 10K and half marathon options in person and virtually during September 2026, with courses on crushed limestone trails and support stations along the routes.

Experience the Bloomingdale Trail Run in Chicago featuring a timed 5K and short dashes for youth. This annual event offers a variety of distances on an urban trail for a family friendly day of running.

Timed 6 hour and 12 hour events on a two mile loop along Evanston’s lakefront and the Northwestern University campus. The course has paved and crushed gravel sections, two aid stations, public fountains, and handcrafted finisher awards.

An annual trail run and family day in Fort Atkinson that raises funds for research into ataxia-telangiectasia. The event includes a 5k trail run, a one mile walk, kids races, and a virtual participation option.

Multi-distance trail event at Tryon Farm featuring a 4 mile loop used for 2 mile, 4 mile, 8 mile, 25k and 50k races. The course mixes grassy fields and single track trails with basic aid and parking across the street.

Trail events at Rock River Heritage County Park on October 3, 2026 include a timed 5K with chip timing and a guided 2.4 mile walk, plus a park celebration with music, food trucks, tastings, and raffles.