Illinois
Illinois Trail Running Calendar 2026-2027
Explore the best trail runs in Illinois for 2026-2027! Our updated list features 101 exciting trail runs across the region. Find your next trail run in Illinois below and join the trail community at these great events!
August 2026
A youth and family 2K obstacle course at Maxwell Park with about 15 obstacles. Waves serve ages 5 and up; participants get a shirt, medal and a timed result, with trophies for top three in each competitive age group.
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.
Awarded OCR Buddy People's Choice, Highlander Assault in Pingree Grove IL offers 3K, 5K and 15K obstacle heats plus night and haunted 5K events.
Hill of a Race 2026 in Bloomington, IL combines a lap based Endurance Challenge with multiple 3 mile obstacle course waves, including competitive men, women, masters and several recreational waves.
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.
Alumni cross country meet in Chicago Heights on August 15 2026 using the old 2 Miles course with decade-based teams, chip timing and place-based scoring.
Trail races at Camp Ondessonk in Ozark, IL featuring 100 mile, 100K, 50K, Night 50K and a half marathon on figure eight loops through sandstone canyons.
A day of looped trail events at Comlara near Hudson, IL, with timed options from one hour to twelve hours, a relay race, and an open course option. Runners complete roughly four mile loops and must return each hour to continue.
Trail races at Paul Douglas Preserve offering approximate 4, 9.5 and 13 mile single-track courses as part of the Dick Pond Athletics Darn Tough Trail Race Series.
A mud obstacle event on August 29, 2026 at Richardson Adventure Farm offering 5K, 15K, timed Infinity laps, Mudder Village, and finisher rewards.
Loop based trail event at Half Day Forest Preserve where runners repeat a 3.1 mile loop, stop after any loop with no penalty, and receive official timing for each completed loop for combined results.
Experience an all terrain trail race through the scenic Big Horse Vineyards featuring natural obstacles and mud. Choose between a competitive 5K or a social beer mile followed by wine tasting in Central Illinois.
A 6 km cross-country race at Lovelace Park in Evanston with scholastic races, team and individual entries, race shirts, awards, and a post-race gathering with food.
September 2026
Test your limits at Decker Farm with a grueling combination of military boot camp and farm chores. Choose between 4, 12, or 36 hour endurance challenges featuring heavy carries and undisclosed physical tasks.
Trail 5K and 10K at Franklin Creek State Natural Area featuring creek crossings, hilly technical terrain, and proceeds benefitting the Franklin Creek Conservation Association.
USATF certified half marathon and 10K on crushed limestone trails at Danada Forest Preserve with chip timing, pacers, shuttle parking and finisher medals.
A 5K trail loop at Rolling Meadows Farm on September 5, 2026, running along the Sangamon River and near the historic Sangamo Town site. Registration runs from June 9 to August 23, with a $35 fee.
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 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.