Grayslake
Trail Running Calendar near Grayslake 2026-2027
Explore the top trail runs near Grayslake for 2026-2027! We've gathered 29 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A Thanksgiving 5K on the Green Bay Trail at Winnetka Train Station featuring rolling start waves, a family division, packet pickup before race day, post-race refreshments, and support for local charities.
A public cross country race in Evanston with three all-grass loops, team and individual scoring, included long-sleeve race shirt, and a post-race awards cookout; entry fees vary by registration date.
December 2026
A dog friendly Canicross event in Lake Geneva with a technical 4 mile loop and an option to run two loops for 8 miles, organized by TYDISH Running.
January 2027
Winter trail race in Crystal Lake with a hilly single-track 10K loop and a 50K made of five laps, staffed aid stations, finisher medals, and age-group awards.
A winter obstacle race at Lake Geneva Ziplines & Adventures on January 30, 2027 offering distances from a kids loop to a 20K Yeti Challenge; fun heats allow optional obstacles while a competitive division awards cash prizes. All in-person finishers r..
April 2027
Trail races in Crystal Lake, Illinois on a 5.2 mile loop offering 50k, 15 mile and 5 mile options through single track, prairie and pine forest.