Trail Running calendar near Waukesha 2026-2027

A memorial 5K run and 2 mile walk in Roscoe, Illinois on October 17, 2026. The out and back course uses local trails and crushed limestone, includes a water station, and offers a virtual supporter option.

Soul Crusher is a trail race in Crystal Lake, IL offering 10 mile and 5 mile options on single track forest trails with looped sections and occasional extra mileage. Packet pickup is available the day before and a 3 hour 30 minute cutoff ap..

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.

Howl-o-ween 5k at Busse Woods is a themed run and walk supporting animal shelters; the chip timed 5k welcomes dogs without separate registration and includes a shirt and finisher medal.

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 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.

A trail running event at Camp Big Timber in Elgin, IL on November 8, 2026 offering 3 mile and 5 mile courses plus a Kids Fun Run. The course includes grass, gravel and a creek crossing and supports 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 community Turkey Trot through Atwood Park near 5k with chipped timing, common trail obstacles and door prizes. No GPS or timing devices are allowed and donations are collected for local causes.

A Canicross-focused trail event at Lake Geneva Ziplines and Adventures offering one 4-mile loop or two loops for 8 miles, dog-powered and dog-friendly options, awards for dog teams, on-course drinks but bring a refillable vessel.

A night trail event near Lake Mills, WI offering 16 and 31 mile out and back runs on flat crushed limestone. Conditions can vary from clear to snowy; required lights and reflective gear are enforced and aid stations operate cupless.

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.

Point to point runs on the Northern Kettle Moraine Ice Age Trail near Greenbush, WI. Options include 50K and 25K with aid stations, drop bag access for the 50K, and bus transport to the start.

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.

Childish Nonsense in Deer Grove Forest Preserve, Palatine IL on April 24, 2027 features looped trail races from 5.5 miles to 50 miles. One aid station at the start/finish is available every 5.5 miles and pacers are allowed for 50 milers aft..