Trail Running calendar near Sherwood 2026-2027

Experience a seven month trail adventure through the scenic parks of Waukesha County. Choose from running, walking, or rucking across distances ranging from 5K to a Half Marathon.

A point to point trail run on the Northern Kettle Moraine Ice Age Trail in Greenbush, WI, offering 25K and 50K options, transport from the finish to starts, aid stations, drop bag access, and post run food.

A spring trail event at the Iola Winter Sports Club offering **5k** and **15k** courses on ski trails and singletrack, plus a free kids 1k when weather permits. Food and drinks will be available in the Chalet and entry fees change after Mar..

Participate in a two mile run or walk through the scenic 120 acre Southern Door School campus. Enjoy a course of gravel and woodland trails while supporting local students and staff in Brussels Wisconsin.

Experience a unique chip timed race in Belgium featuring road and trail sections through Harrington Beach State Park. Choose between a fast 5k road course, a 10k hybrid trail run, or a scenic half marathon with Lake Michigan views.

Experience the diverse landscapes of Shiocton at the Navarino Nature Center Trail Run. Run or walk through forests and across bog boardwalks to support environmental education and local trail improvements.

A low-impact trail event at Lapham Peak Park offering distances from a Kiddos 1K to a half marathon, with ruck and walk options, cupless aid stations, and proceeds benefiting Tall Pines Conservancy.

Experience a unique two mile obstacle course at Alsteen Farms featuring real farm chores like tire throwing and calf feeding. Enjoy a yogurt bar and an optional dairy farm tour after the event.

Experience a scenic point to point run from Plover to Amherst along the Tomorrow River Trail. This half marathon concludes at the Central Waters Brewing Co for a memorable finish in Wisconsin.

The First Mondays Summer Trail Series is a summer trail running event at the Iola Winter Sports Club. A different 5 km course is featured each month in June, July, and August. The series includes a vertical hill challenge and a kids race.

Experience Door County's first trail run at the Crossroads at Big Creek Nature Preserve with 2K 5K or 10K courses that reward participants with a native tree.

A multi-duration trail event at Camp Sinawa near Valders, WI featuring a 4.5-mile loop with 330 ft gain per lap. Registration opens Jan 2, 2026; online registration closes June 24 and there is no race-day registration.

Take on the Cliff Runner 10K on July 19, 2026 at High Cliff State Park, a rugged singletrack course with rocks, roots and steep climbs. Registration includes a Cliff Runner tee and finisher medal, with proceeds to Purdy Nature Preserve.

A 9 mile evening trail run at Kohler-Andrae State Park that follows woodland trails, shoreline sand and a 1.45 mile cordwalk. The course has a three hour cutoff, one aid station and a cupless policy.

Take on a scenic one mile loop at Lapham Peak with 24, 12, and 6 hour timed options or set distance goals like a marathon or 50 miles. Lighted night laps, a stocked aid station, and a welcoming club vibe make every lap count.

Trail marathon and half marathon at High Cliff State Park near Sherwood, Wisconsin, featuring singletrack, prairie sections and views of Lake Winnebago and the Niagara Escarpment. The event is cupless and includes aid stations and a postrac..

Event Overview The HELP in Motion Trail Run takes place from October 1 to 31, 2026. The event raises awareness about domestic violence, honors lives lost, and supports survivors. Event Details Participants can choose from an in-person trail..

Tackle a 1.5-mile farm-themed obstacle course at Heim's Hillcrest Dairy. The event features challenges like feeding calves, flipping tires, and climbing hay bales. Afterwards, enjoy a yogurt bar and an optional farm tour.

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.