Trail Running calendar near Valparaiso 2026-2027

A daylong, in-person endurance event where runners complete a marathon by running 1.09 miles every hour and resting on site between efforts, with camping allowed and a finisher medal awarded.

Oakadoke Trail Runs in Valparaiso, IN features single track trails with varied terrain and pond views. Three distances are offered, aid stations are spaced along the route, and a post race meal is provided; the event is cupless.

Continuous 3.1 miles loop race at Deer Grove East offering 40 or 50 mile options with a 12 hour cutoff. Centralized aid every lap, designated crew access, pacers allowed, and on-course medical support.

Loop-based trail event at Deer Grove East Forest Preserve in Palatine, Illinois. Distances run from 5K to 50K and each lap returns to a central aid station so athletes can decide how far to continue.

A retro 5K cross-country race by Fox River Trail Runners at Settler's Hill in Geneva. Entry fees are $10 for members and $12 for non-members, and proceeds support the course's preservation.

A women only 5K obstacle mud run at Wildcat Creek MX in Rossville, Indiana on August 9, 2026, featuring 18+ obstacles and open to participants aged 7 and up. Participants can run, jog or walk the muddy course.

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 5K chip-timed run and a 3K scavenger-hunt walk through St. Patrick's County Park featuring trail terrain, participant medallions, post-event refreshments, awards by age group, and proceeds that support park programs.

Loop based endurance event at Busse Woods on August 15, 2026 offering repeated 3.1 mile laps over smooth crushed limestone and packed gravel. Distances range from 5K to 50K with a central aid station and open loop format.

Continuous 3.1 mile loop at Busse Woods near Elk Grove, IL offering 40 and 50 mile options with a fully stocked aid station every lap and a 12 hour cutoff. Runs alongside The Next Loop series but is scored separately.

A free alumni 2 Mile cross country meet on 08/15/2026 in Chicago Heights that uses chip timing and decade-based teams and head-start groups, with team scoring based on finishing place.

Trail races of approximately 4, 9.5 and 13 miles at Paul Douglas Forest Preserve with water stations, age group awards and CAMBr as beneficiary.

A 10 hour endurance run at Bluhm County Park on August 29, 2026 with repeated 4 to 4.1 mile trail loops, hourly cutoffs, and a chip based prize system.

A continuous loop trail race at Half Day Forest Preserve near Vernon Hills, Illinois. Runners complete repeated 3.1 mile loops toward a 40 or 50 mile total with a 12 hour cutoff and a fully stocked aid station each lap.

Looped trail event at Half Day Forest Preserve in Vernon Hills with a 5K loop and multiple distance options. The course runs on crushed limestone, gravel, and natural trails through woodlands, prairies, and riverfront scenery.

A 3.62-mile all-grass cross-country race at Lovelace Park in Evanston with individual and team entries, tiered entry fees by registration period, a performance shirt with entry, and a post-race awards gathering with food.

Trail half marathon and 10K at Danada Forest Preserve in Naperville with USATF certified courses, chip timing and finisher medals.

A casual farm-based fun run on September 5, 2026 at Gast Family Farms offering a 5K and 1 Mile through farm fields; $10 registration supports the Lakeshore Lions and includes a shirt, medal, and grape juice.

A community run at Woodland Middle School in Gurnee on September 11, 2026, offering a 5K, 1 Mile, and a shirt only option. Proceeds support the Woodland PTA and confidential financial assistance for fees is available.

A remembrance event at the Lake County Fairgrounds Grandstand in Crown Pont, IN where participants climb 17 laps totaling 1,980 steps or join a 1 mile non timed walk. The event includes hero wristbands, limited finisher medals, and supports..