Trail Running calendar near Winnetka 2026-2027

Loop format trail event at Busse Woods in Ned Brown Forest Preserve on August 15, 2026. Runners complete 3.1 mile loops on crushed limestone and packed gravel with a centralized aid station and distances from 5K to 50K.

A continuous 40 or 50 mile loop race at Busse Woods on a 3.1 mile (5K) trail loop with fully stocked aid each lap and a 12 hour time limit. Personal supplies, crew zones, pacers, and on site medical staff support runners.

Run the Rails in Elburn, Illinois on August 22, 2026 offers a 1 mile fun run plus 4 mile and 7 mile courses that begin and end at Prairie Park. Courses cross the Union Pacific West rail line and benefit the Elburn Parks Commission.

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.

Timed ultrarunning at Lapham Peak State Park with 24, 12 and 6 hour options plus a distance division for marathon and longer targets. One mile loop, chip timing, an aid station, and a cupless refill policy.

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 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.

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.

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.