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.
August 2026
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.
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.
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.
September 2026
Timed 12 hour and 6 hour races on a 2 mile lakeside loop in Evanston with aid stations, public fountains, and handcrafted finisher awards.
Backyard Nonsense on September 26, 2026 at Richard Bong State Recreation Area offers 24 hour and shorter timed trail races, including a Backyard 12 loop format.
October 2026
Trail races on the flat, crushed gravel Des Plaines River Trail in Lake County offering Half Marathon, Marathon, 50K and 50 Mile distances.
Trail race in Crystal Lake on October 17, 2026 with 5 and 10 mile courses through Veteran Acres and Sternes Woods, race shirt and finisher medal included.
Oct 18, 2026 in Spring Grove: run through a corn maze and farm with 10K, 5K including a 250 turn maze option and a 1 mile Family Adventure, plus finisher medals.
A Halloween-themed trail event in Pingree Grove, IL on October 23, 2026 with multiple 5 km heats, haunted sets and animatronics, plus a costume contest, bonfire and food; spectator fee $10, free parking.
Howloween 5K in Schaumburg is a chip timed 5K run or walk at Busse Woods that supports animal shelters. Pets may join without registration and a virtual participation option is available.
November 2026
A 3-mile cross-country race at the MacNider course in Schaumburg on November 8, 2026, with separate women's and men's races, optional team scoring, pre-race packet pickup, and a $25 registration fee.
On 11/14/2026 the Abominable Trail Race at Lake Geneva Ziplines & Adventures offers 5K, 10K, 15K and 30K courses plus 2, 3 or 4 person 30K relays on forest trails, with water stations, race shirt, finisher medal and free action photos.