Trail Running calendar near Terre Haute 2026-2027

A community event in Velpen, IN on August 8, 2026 featuring a 5K, a 10K trail and ruck run, plus a virtual option. Proceeds support local police and the event honors veterans, emergency personnel and those lost on 9/11 and after.

Trail run at Southwestway Park in Indianapolis on August 15, 2026, offering 5K and 15K courses over hilly mixed-surface trails. It is the final race of the DINO 5K/15K series and includes awards plus a free kids run.

Hit the Wild Wild Wilderness at Kickapoo State Recreation Area on September 12, 2026 with 5K or a rugged 7.45 mile trail through woods, steep climbs and creek crossings. Celebrate finishes with food, drinks and awards.

Trail races at Willenborg Woods near Charleston, Illinois on October 16 and 17, 2026. Multiple distances from 5K to 100K on marked single-track trails with riverside sections, creeks, hills, volunteer support and a post race celebration.

An annual trail running festival at Yellowwood State Forest on October 17, 2026, with distances from 8 miles to 50k including a 2-4 person 50k relay, festival camping, course maps and GPX files, aid station support, and post-race awards.

A trail event at Robert Allerton Park in Monticello on October 25, 2026, featuring a 5.7 mile run, a 2 mile nature walk, and a virtual 5.7 mile option. A portion of proceeds supports park trail maintenance and improvements.

Join the Monster Dash in Bloomington for a fun 1 mile or 5K along the Karst Greenway Trail, where costumes, dogs and strollers are welcome. Enjoy free race photos and support the Auxiliary to the Boys and Girls Club.

The Krampus will take place in Indianapolis on Friday 4 December 2026. You can run 5 kilometers.

The FroMoMoFo 20 Miler will take place in Martinsville on Sunday 17 January 2027. You can run between 10 and 20 miles.