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Trail Running Calendar near Bloomington 2026-2027

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Explore the top trail runs near Bloomington for 2026-2027! We've gathered 8 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
9
Su

To the Max Obstacle Challenge

Obstacle Run
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.
Aug
15
Sa

Hill of a Race

Obstacle Run 3 mi
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.
Aug
22
Sa

Comlara Trail Run

Trail Run
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.
October 2026
Oct
3
Sa

Run the Woods

Trail Run Walk 5 km 8 km
Run The Woods is a trail event at Timber Pointe Outdoor Center in Hudson, IL featuring 5K and 8K races with youth divisions and a one mile untimed trail walk. Proceeds benefit Easterseals Central Illinois and Timber Pointe Outdoor Center.
Oct
18
Su

Oktoberfest Rotary Run

Trail Run 5 km
A chip timed 5K and an untimed 1 mile fun walk at GE Park in Bloomington on October 18, 2026, raising funds for BN Sunrise Rotary Youth Services and the CCHS Rotaract Club. Awards include ceramic steins for top 5K age group finishers.
December 2026
Dec
5
Sa

Da Deer Run Run

Trail Run 4 km 8 km
Experience a cross country style trail race through the Timber Pointe Nature Center at Lake Bloomington. Choose between 4K and 8K loops or a three hour endurance challenge while supporting local nature conservation.
March 2027
Mar
27
Sa

Clinton Lake Ultra

Trail Run 10 mi 30 mi
Trail races at Clinton Lake State Recreation Area with a three-loop 30-mile option and a 10-mile course, two aid stations per loop, no chip timing, and a volunteer requirement.
June 2027
Jun
13
Su

Mackinaw Valley Wine Run 5K

Trail Run Walk 5 km
Vineyard 5k at Mackinaw Valley Vineyard and Winery on June 13, 2027 with post race wine, chip timed results, and age group awards.
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