Trail Running calendar near Waukesha 2026-2027

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 championships in Kenosha, WI on November 28, 2026, featuring multiple 5K races and a 3K youth event. Top finishers in the championship race can qualify for the Brooks XC National Championships in San Diego.

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 trail event at Lake Geneva with 4- and 8-mile loop options, basic aid, and dog-specific awards.

Nighttime out and back runs of 31 mile and 16 mile on a flat rails to trails course in Lake Mills WI with required lights and reflective gear.

The Frozen Gnome will take place in Crystal Lake on Saturday 9 January 2027. You can run between 10 and 50 kilometers.

A winter trail series at Dick Young Forest Preserve in Batavia featuring 5K, 8K, and 10K races on separate dates in early 2027, with combined registration and a series swag reward program.

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 f..

Trail races at Oakhurst Forest Preserve in Aurora, Illinois, the series includes 5K, 8K, and 10K events in early 2027 with a single registration and series swag rewards; the 8K fee is $65.00.

A winter timed ultra in the Southern Kettle Moraine Forest offering 6, 12 and 24 hour loop options for solo runners and relay teams. The field is limited to 160 participants and the 6 hour option is available in AM and PM waves.

A 10K trail race at Hickory Knolls Discovery Center in St. Charles, IL with a $70 entry fee. The race is part of a winter series that also includes a 5K and 8K and uses a single registration page.

Point-to-point trail run on the Northern Kettle Moraine Ice Age Trail near Greenbush, WI, with 50K and 25K options, aid stations, and post-run refreshments.

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.

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.

Trail ultraraces at Deer Grove Forest Preserve in Palatine IL featuring 5.5 mile laps, central aid station, inclusion policies and a playful race atmosphere.

A chip timed 10k combining 5 miles of road and a 1.2 mile trail through Harrington Beach State Park with mowed grass paths, rolling hills and possible wet areas.

Trail races at Donald County Park include 5 km, 15 km and a Kids One Mile Fun Run across prairie, single-track, sand and bridges. Proceeds support Friends of Donald Park for trail maintenance and repair.

Flat out and back half marathon and 10K on the limestone Great Western Trail with a 25 plus year history and proceeds supporting local mental health charities.

A trail event in Belleville, WI on May 29, 2027 featuring 50 mile, 50K and half marathon options on flat rail trails with aid stations and free post-race food.

The Kishwauketoe 5K will take place in Williams Bay on Saturday 3 July 2027. You can run 5 kilometers.