Trail Running calendar near Sheboygan 2025-2026

Run the Warrior 5K or 8K at Greenfield Park in West Allis. Scenic wooded trails, team and individual entries, shirts, awards and post race snacks. Proceeds benefit Wisconsin Lutheran College and a local charity.

Join Run Til You Snowdrop, a 24 hour treadmill event in Appleton on Nov 8 and 9 that raises funds and honors families affected by pediatric cancer. Teams and individuals keep treadmills running at Crunch Fitness to support the Snowdrop Foun..

Join the PRO Mixed XC Relay at Mitchell Park in Brookfield on Nov 9, a four leg mixed relay with each teammate running a 3K in male female male female order. Open to clubs and individuals with Youth, High School, Open and Masters divisions.

Join the Bucks & Does 13.1 Pointer on November 15, 2025 in Nashotah Park for scenic wood chip trail races including a half, 10K, 5K and a kids Bambi Run. Enjoy shaded paths, chip timing and a unique finisher woodle.

Run the inaugural Fast Eddie 50K or the popular 5K at Lapham Peak, enjoying scenic woodland loops and rolling trails. All entry proceeds benefit the Little Warrior Foundation supporting children facing cancer.

Run the peaceful Glacial Drumlin State Trail at the Quiet Silence 50k in Lake Mills, WI, with 50k and 25k routes on crushed gravel. This timed race awards top finishers and asks runners to keep quiet for nearby neighborhoods.

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..

Take on ARKTOS Feb 28 to Mar 1 2026, a winter loop ultra in Wisconsin's Southern Kettle Moraine. Run solo or with a team of up to 4 in 6 Hour, 12 Hour or 20 Hour timed loops for cold weather challenge and community fun.

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..

Run the NK50k in Greenbush, Wisconsin on April 11, 2026. Choose 50K or 25K point to point routes across rolling ski tracks, rocky Ice Age Trail sections and lofty ridgelines, with aid stations, shuttle service and post run food; expect to b..

Run under the stars at Moonlight Meltdown on April 25 in Belgium WI, with chip timed 5k road and a Sunset Safari 10k including a trail through Harrington Beach State Park. Shirts, post race food and a finish party at KYOTES.

Test your limits on scenic loops through Southern Kettle Moraine at the Prickly Pine Jackpot 24 Hour in Dousman, WI. Choose 3, 6, or 9 mile loops for 6, 12 or 24 hour solo and relay races and chase a cash jackpot for top finishers.

Join the 17th annual Crossroads Trail Run & Walk at Big Creek Nature Preserve in Door County for scenic 2K, 5K and 10K courses. All participants receive a native tree and post race snacks while supporting conservation and outdoor education.

Tackle a rugged 10K through High Cliff State Park's single track trails of rocks, roots and steep climbs for an unforgettable challenge. Finishers receive a Cliff Runner shirt and medal and proceeds support the Purdy Nature Preserve.

Run or walk the Jazz Blueberry Trail at Jazz Blueberry Farm in Shelby on July 26, enjoying scenic grass and dirt trails through the farm. Options include a 1 mile fun run, 5K or 10K for a family friendly day with shirts and awards.

Enjoy a scenic 9 mile trail loop at Kohler Andrae State Park featuring beaches, boardwalks, marsh and pine trails along Lake Michigan. Friendly cupless race with post race food, awards and a commemorative finisher token.

Experience a spirited trail running weekend with 50 mile and 50K ultras plus marathon and half marathon options, famed for huge finisher medals and a lively post race party. Registration for 2026 is closed but a wait list will open soon.

Challenge yourself on rugged single track and rolling prairie at Twisted Roots, offering marathon and half marathon distances with views of Lake Winnebago and the Niagara Escarpment. Trail etiquette required; bring your own cup.