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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 5 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

Trail Running Calendar United States
October 2026
Oct
3
Sa

Run the Woods

Trail Run 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 ultramarathon at Clinton Lake State Recreation Area with 30-mile (three 10-mile loops) and 10-mile options, aid stations, and a mandatory volunteer requirement.
June 2027
Jun
13
Su

Mackinaw Valley Wine Run 5K

Trail Run 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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