Trail Running calendar near Sheboygan 2025-2026

The Golden Pines Trail Run at Machickanee, held in Abrams, Wisconsin, offers an evening trail running and hiking experience through the scenic Machickanee Hiking and Ski Trails. Participants can choose from 7K or 11K distances, with options..

The First Annual Paws for a Cause Canicross & Trail Run/Walk for Charity takes place in Denmark, Wisconsin, offering participants the chance to run or walk scenic wooded trails with or without their dogs. The event features three distance o..

Zachariah's Acres Fall Run, Walk & Roll is held in Oconomowoc, Wisconsin, on a scenic 125-acre private property featuring tree-lined paths, wildflowers, prairie grass, ponds, and vibrant fall colors. The event offers a 5K, a half marathon,..

Wiglorious Day is a Southern Kettle Duathlon held at Lapham Peak State Park in Delafield, Wisconsin. The event includes three distances: a 5-mile run, a 5-mile bike, and a final 5-mile run, with options for solo competition or 2- or 3-perso..

Race For Open Space is a West Bend, Wisconsin trail running event at Cedar Lakes Conservation Foundation's Fox Hill Nature Preserve. It offers a 5K trail run, a 10K trail run (two loops), a 1-mile trail walk, and a 5K for ages 18 & under. T..

Conquer Triangle Hill at Run for the Hill of It on October 18 in Green Bay, a scenic 5K trail run with kids, dog walk, and virtual options. Proceeds support Baird Creek Greenway and finishers get shirts, snacks, and king and queen honors.

Among the Trees is an ultramarathon event held in Dousman, Wisconsin, featuring 100k and 50k race distances. Set within the scenic Southern Kettle Moraine Forest along the historic Ice Age Trail, the course offers runners a challenging and..

Warrior 5K & 8K...Through The Park is a fall trail running event held at Greenfield Park in West Allis, Wisconsin. The weekend offers a 5K Run, 8K Trail Run, a 2.25 Mile Walk, and team options for the 5K and 8K, with cross-country-style sco..

Run Til You Snowdrop-24 Hour Treadmill Run is a charity endurance event held in Appleton, Wisconsin, at Crunch Fitness (2500 S. Kensington Drive). The fundraiser runs for 24 hours on 24 treadmills to support the Snowdrop Foundation of Wisco..

PROMixed XC Relay is held at Mitchell Park in Brookfield, Wisconsin (19900 River Road). The mixed-gender relay features four runners per team in the order male, female, male, female, with each athlete running 3000 meters. The event, backed..

Event overview The Fast Eddie 50k/5k takes place on Saturday, November 15, 2025, at Lapham Peak in Delafield, Wisconsin. The event includes the following distances: 50K 5K The location listed is W329 N, 846 County Trunk Hwy C, Delafield,..

The Bucks & Does 13.1 Pointer is a trail running event held in Nashotah Park, Wisconsin, featuring distances of 5K, 10K, and a half marathon (13.1 miles). The course is primarily wood-chipped with some grassy sections, shaded by trees for a..

The Quiet Silence 50k is an ultramarathon held in Lake Mills, Wisconsin, featuring an out-and-back course on the Glacial Drumlin State Trail. Starting at Rotary Park in Lake Mills, runners head west to the trail's terminus in Cottage Grove,..

Whitewalker Ultra 100k is a self-supported ultramarathon held in Palmyra, Wisconsin, starting at Emma Carlin Trailhead. The course comprises two 50k loops, first looping west on the Ice Age Trail to Whitewater and back, followed by a second..

ARKTOS : February 28 to March 1, 2026 ARKTOS is a winter trail ultra held in Dousman, Wisconsin (Southern Kettle Moraine Forest). The event offers timed-loop formats in three durations. The race is open to solo runners and relay teams of up..

Trailbreaker : March 29, 2026, Waukesha, WI The Trailbreaker is scheduled for March 29, 2026, in Waukesha, WI, with the main venue at the Schuetze Recreation Center / Frame Park Baseball Stadium. The event has been hosted by the Park Founda..

Event overview NK50k takes place on April 11, 2026 in Greenbush, WI, presented as the 13th Annual-ish edition. The event offers multiple distances: 50K - point-to-point on the Northern Kettle Moraine Ice Age Trail 25K - separate start at C..

The Sunset Safari 10k Trail Run is part of the annual Moonlight Meltdown event held in Belgium, Wisconsin. This hybrid trail run features a 6.2-mile course combining a 5-mile road segment with a 1.2-mile trail section through Harrington Bea..

The Prickly Pine Jackpot 24 Hour Solo/Relay is an endurance running event held in the scenic Kettle Moraine State Forest near Dousman, Wisconsin. Participants can choose from multiple race options including 6-hour, 12-hour, and 24-hour solo..

The Crossroads Trail Run & Walk, held annually at Crossroads at Big Creek Nature Preserve in Sturgeon Bay, Wisconsin, offers a scenic trail running experience with three distance options: 2K, 5K, and 10K. This event welcomes runners and wal..