Trail Running calendar near Glendale 2026-2027

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.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

Trail running event on October 31, 2026 at the Greenbush trail system near Glenbeulah, WI. Choose a 5K one loop or a 10K two loop course; chip timing is provided and a park sticker or daily pass is required.

A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding forest projects.

Trail runs and a walking option use a rolling park course that starts at the southwest corner and returns through woods, service road, and open sections with occasional rough footing and visible seasonal foliage.

Trail running at Camp Big Timber in Elgin, IL on November 8, 2026, featuring 3 and 5 mile perimeter courses with a creek crossing. A kids fun run and a pancake breakfast are included, and proceeds support local youth organizations.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

Bucks & Does 13.1 Pointer is a multi-distance running, walking, and ruck event at Nashotah Park on 11/14/2026. Distances range from a youth Bambi Run to a 13.1 Pointer, and every finisher receives a wooden finisher medal.

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.

Regional cross country meet in Kenosha, WI on November 28, 2026, featuring multiple 5K championship races, a youth 3K, and team pricing with qualification spots to the Brooks XC Nationals.

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.

A canicross-focused event at Lake Geneva with 4-mile loops (option to double for 8 miles), technical single-track trails, dog-specific awards, on-course hydration refills, and rules to protect the venue and wildlife.

A night trail event in Lake Mills WI with 16 mile and 31 mile out and back options on flat crushed limestone. Winter trail conditions vary and aid, drop bag rules, and required lights and reflective gear differ by distance.

A winter obstacle race at Lake Geneva offering 5K, 10K, a 20K Yeti Challenge, a kids course, team packs and a virtual option. Fun heats allow skipping obstacles while the Elite division requires full obstacle completion for podiums.

A winter timed ultra in Dousman, Wisconsin offering 6, 12, and 24 hour options for solo runners or relay teams of up to four, set in winter woods and on a frozen lake with warming shelters, hot drinks, a meal, and finisher items included.

A point-to-point trail run in Greenbush, WI on April 3, 2027, offering 50K and 25K options along the Northern Kettle Moraine Ice Age Trail with on-course aid, post-run refreshments, and transportation from the finish to the starts.

Trailbreaker returns to Waukesha on April 4, 2027 with races from a 1K kids run to a full marathon, plus ruck options and a walk. Proceeds support the Park Foundation of Waukesha and local parks and recreation.

A trail event at Deer Grove Forest Preserve near Palatine, IL on April 24, 2027, offering 5.5 mile, 25K, 50K and 50 mile distances with a single aid station at the start and a playful, community-focused atmosphere.