Trail Running calendar near Brookfield 2026-2027

Timed ultraruns in Southern Kettle Moraine Forest on Oct 10 to Oct 11, 2026. Solo runners or teams of up to four complete as many 3, 5, or 6 mile McMiller Trail loops as possible in 6, 12 or 20 hour formats.

Multiple endurance trail distances on a flat, crushed gravel section of the Des Plaines River Trail, starting and finishing at Half Day Forest Preserve in Lake County, Illinois. The marathon is a Boston Qualifier and the event runs each Oct..

Trail runs and a 1-mile walk at Fox Hill Nature Preserve on 10/11/2026, held to support conservation in the Cedar Lakes region; varied distances include 5K, 10K, a 1-mile walk, and a Kiddos 1K.

A fall ultramarathon on the Ice Age Trail near Greenbush, Wisconsin offering 50 mile and 50K out and back courses. Aid stations are spaced four to eight miles and the event is cupless with reusable cups provided at check in.

A memorial 5K run and 2 mile walk in Roscoe, Illinois on October 17, 2026. The out and back course uses local trails and crushed limestone, includes a water station, and offers a virtual supporter option.

October 17, 2026. A trail race in Crystal Lake, IL with 5 mile and 10 mile options on single-track trails through Veteran Acres and Sternes Woods, cup-less aid, and a 3 hour 30 minute cutoff.

A fall event at Richardson Adventure Farm in Spring Grove, IL featuring 5K and 10K courses through the corn maze and farm, a family 1-mile run for children, and a kids 100m dash with ribbons for finishers.

A Halloween-themed trail event in Pingree Grove, IL on October 23, 2026 with multiple 5 km heats, haunted sets and animatronics, plus a costume contest, bonfire and food; spectator fee $10, free parking.

Howloween 5K in Schaumburg is a chip timed 5K run or walk at Busse Woods that supports animal shelters. Pets may join without registration and a virtual participation option is available.

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.

Trail running event on October 31, 2026 at the Greenbush trail system near Glenbeulah, WI. Choose a 5K one loop or a 10K two loop course; chip timing is provided and a park sticker or daily pass is required.

A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding forest projects.

Trail runs and a walking option use a rolling park course that starts at the southwest corner and returns through woods, service road, and open sections with occasional rough footing and visible seasonal foliage.

Trail running at Camp Big Timber in Elgin, IL on November 8, 2026, featuring 3 and 5 mile perimeter courses with a creek crossing. A kids fun run and a pancake breakfast are included, and proceeds support local youth organizations.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

Bucks & Does 13.1 Pointer is a multi-distance running, walking, and ruck event at Nashotah Park on 11/14/2026. Distances range from a youth Bambi Run to a 13.1 Pointer, and every finisher receives a wooden finisher medal.

A community Turkey Trot through Atwood Park near 5k with chipped timing, common trail obstacles and door prizes. No GPS or timing devices are allowed and donations are collected for local causes.

A Thanksgiving 5K on the Green Bay Trail at Winnetka Train Station featuring rolling start waves, a family division, packet pickup before race day, post-race refreshments, and support for local charities.

Regional cross country meet in Kenosha, WI on November 28, 2026, featuring multiple 5K championship races, a youth 3K, and team pricing with qualification spots to the Brooks XC Nationals.

A public cross country race in Evanston with three all-grass loops, team and individual scoring, included long-sleeve race shirt, and a post-race awards cookout; entry fees vary by registration date.