Trail Running calendar near St. Charles 2026-2027

Trail 5K and a children's 1/4 mile at Kishwauketoe Nature Center in Williams Bay. The grass trail course passes through hills, woods and prairie, includes a water stop, parking across the street, and awards for top finishers.

A prairie trail run and walk at Lapham Peak State Forest on July 11, 2026 that raises funds for prairie management, offers awards and shirts for early participants, and includes merchandise, seed sales and on-site food.

A trail 5K at Byron Forest Preserve with chip timing and awards by age group, plus a 1 mile Fun Run with a participation medal. Parking and indoor restrooms are available onsite.

H-F Beast Obstacle Course Dash in Homewood, IL on July 12, 2026 features two age categories with obstacle runs. The event awards finisher medals and t shirts and includes an optional prep course in June.

An overnight loop endurance event at Lowell Park in Dixon, IL where participants repeat a .411 mile paved loop for 6, 12, or 24 hours. Solo and three person relay options are available and the event is self supported.

Oakadoke Trail Runs features tree-covered single-track, switchbacks and creek crossings on looped 4, 9 and 18 mile courses near Valparaiso, IN, with frequent aid stations and a cupless race format.

A 10K walk/run on August 1, 2026, through the Nordic Trail System in Kettle Moraine State Forest with water refill stations, trail snacks, a cup-less policy, and donations supporting The Salvation Army.

Night trail races in Dixon Illinois on an approximate 5 mile loop with solo distances and a three person relay, single aid station, post race snack, and on site tees for all participants.

A community cross country event in Mount Prospect offering 1, 2 and 3 mile races. Entry is $25 and proceeds benefit the Little Giraffe Foundation.

A Scottish Highlander themed obstacle race in Pingree Grove, Illinois featuring 3K family, 5K and 15K heats with 20 to 30 obstacles, plus a torch lit night race and a haunted 5K. Spectator fee on-site is $10 and parking is free.

Run the Rails in Elburn, Illinois on August 22, 2026 features a 1-mile fun run plus 4- and 7-mile courses that start and finish at Prairie Park. The routes cross the Union Pacific West rail line and benefit the Elburn Parks Commission.

Trail race at Paul Douglas Forest Preserve on August 23, 2026 offering approximate 4, 9.5 and 13 mile courses. Part of the Dick Pond Athletics Darn Tough Trail Race Series with proceeds benefiting Chicago Area Mountain Bikers.

Tough Mudder Chicago at Richardson Adventure Farm on August 29, 2026 combines mud and named obstacles with 5K, 15K, and Infinity lap options plus a Mudder Village festival and finisher rewards.

A 10 hour endurance run at Bluhm County Park on August 29, 2026, using a 4 to 4.1 mile loop completed on an hourly clock. Runners earn chips after four loops to trade for prizes and receive a limited edition shirt and wooden medal.

A technical trail event at Franklin Creek State Natural Area offering 5K and 10K courses with multiple creek crossings and forested, hilly terrain. Proceeds benefit the Franklin Creek Conservation Association.

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 USATF-certified half marathon and 10K through Danada Forest Preserve on crushed limestone trails, finishing near the horse track. Both distances award finisher medals, with chip timing, pacers, shuttle parking, and on-course water station..

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 running event in Chicago with 3 hour, 6 hour and 12 hour formats plus relay teams. Runners complete repeated roughly 1 mile paved loops in a 58 acre park and face a new challenge every hour.

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.