Trail Running calendar near Sherwood 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..

The Iola Fall Classic Trail Race is a new annual event hosted by the Iola Winter Sports Club in Iola, Wisconsin. It features three trail races—the 25k, 10k, and 5k—set on a mix of single-track and cross-country ski trails. The event emphasi..

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.

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..

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 Dormie Challenge: 12-Hour and 6-Hour Ultra Marathon The Dormie Challenge takes place on Saturday, May 30, 2026, in Stevens Point, Wisconsin. The event offers two timed ultra marathon options: 12-hour and 6-hour. The course is a 1.01-squ..

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..

Cliff Runner 10K is a challenging 10-kilometer trail race held in Sherwood, Wisconsin at High Cliff State Park. The course takes runners along mostly single-track trails through the park’s rugged terrain, featuring rocks, roots, boulders an..