Trail Running calendar near Sherwood 2026-2027

Celebrate the season with a 5K run through the scenic trails of Brown County Reforestation Camp. Finishers get a bottle of local maple syrup, and a pancake breakfast is included. The event also features a family-friendly fun run and support..

Event Details The NK50k is an annual fun run scheduled for April 11. It features 50K and 25K distances. The event is a point-to-point tour on the Ice Age Trail in the Northern Kettle Moraine State Forest, starting from the Ridge Road Trailh..

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..

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.

The Conservation Chase is a trail running event at Lapham Peak State Park supporting local conservation. Choose from distances including a half marathon, 10K, 5K, and ruck or walk options. It's a cupless race with proceeds benefiting the Ta..

This point-to-point half-marathon travels from Plover to Amherst, Wisconsin, with over nine miles on the scenic Tomorrow River Trail. The finish line is at Central Waters Brewing Co. Register by early May to secure your t-shirt size.

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.

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.

Thanks Sandy is a 9 mile trail run through the scenic Kohler-Andrae State Park in Wisconsin. With a flat course along Lake Michigan and a boardwalk section, it offers a unique evening race. All finishers receive a commemorative token.

Twisted Roots is a trail running event at Wisconsin's High Cliff State Park, featuring marathon and half marathon distances. Runners will experience a mix of technical single track and prairie terrain with views of Lake Winnebago. The cuple..

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..

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.

A fall event at Zachariah's Acres in Oconomowoc that raises funds for children with special needs. Routes include a half marathon, two 5K options including ruck, and a one mile family walk and roll through prairie and woodland scenery.

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 charity trail run or walk in Denmark, Wisconsin. Choose your distance for canicross with your dog or go solo on the wooded trails. The event includes a costume contest and supports the Crisis Cafe.