Trail Running calendar near Whitewater 2026-2027

A grassroots multi-distance trail event in Dixon, IL using a roughly 7.85 mile loop for 25K, 50K, 100K, and 100 mile races, with mixed singletrack, meadow and gravel terrain, two aid stations, crew access, and pacer allowances.

Experience natural dirt trails and scenic views at this Janesville event featuring a competitive 5k run and casual walk. Stay for the heritage celebration with food trucks and live music after you finish.

Explore the scenic trails and steep hills of Mirror Lake State Park with several distances available. Finish your race with refreshments and s'mores around a campfire while supporting local park projects.

Experience a chip timed 5k trail run through the diverse terrain and scenic landscapes of Oakdale Nature Preserve. All proceeds support local park projects and trail maintenance.

Run or walk along the tree lined Oak Leaf Trail before finishing at the Oktoberfest celebration in Glendale. This event features a 5k run and a 54 yard dash with post race refreshments and festival entry.

Participate in a half marathon, 5K, or rucking event at Zachariah's Acres in Oconomowoc. Support nature based programs for children with special needs while exploring prairie trails and wildflowers.

Experience the rugged beauty of Wisconsin's Driftless Area with a looped trail run featuring technical singletrack and rocky climbs. Choose between 50K, 20 mile, or 10 mile distances atop scenic bluffs.

A flat, fast trail event along the Des Plaines River Trail in Lake County, Illinois, offering 50 mile, 50K, marathon and half marathon distances, manned aid stations, finisher medals, and a Boston qualifying marathon.

Run or walk through the beautiful Fox Hill Nature Preserve this fall. Choose from trail runs, a walk, or a kids' race, all supporting local land conservation. Experience deciduous forests, restored prairies, and scenic glacial moraines.

Join the Jaimie Cox Memorial Run on October 17, 2026 in Roscoe, Illinois for a community 5K or 2 mile walk along the scenic Stone Bridge Trail. Family friendly with kids and virtual options, supporting the Jaimie Cox scholarship.

A trail race in Crystal Lake, IL on Oct 17, 2026 offering roughly 5- and 10-mile single-track loops through Veteran Acres and Sternes Woods. The event is cup-less, includes a finisher medal, and has a 3 hour 30 minute cutoff.

Experience a haunted 5k trail run in Pingree Grove featuring live actors and animatronics. Stay for the bonfire and costume contest at this unique evening event.

Celebrate Halloween and support animal shelters at this dog friendly 5k in Busse Woods. Enjoy a flat paved course with treats for both humans and leashed pets at the finish line.

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.

Embrace an autumn adventure at the Big Timber XC Challenge, a trail run featuring a famous creek crossing through the woods of Camp Big Timber. Choose between a 3-mile or 5-mile course on grass and gravel paths. All runners get a shirt and..

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.

A winter trail event at Governor Dodge State Park on Dec 5, 2026 offering 50K, 25K and 15K over horse trails, single and double track with multiple aid stations, cup-less hydration, and specific pacer and crewing rules for the 50K.

Experience a unique winter obstacle course in Lake Geneva featuring distances from 5K to 20K. Enjoy a festival atmosphere with fire pits and food trucks after conquering challenges designed for both fun and competitive athletes.

Experience a unique 5K race held entirely on the frozen surface of Lake Mendota. Participants can run walk or skate across the ice while enjoying scenic views of downtown Madison and the university campus.