Trail Running calendar near Sheboygan 2026-2027

A fall ultramarathon on the Ice Age Trail near Greenbush, Wisconsin offering 50 mile and 50K out and back courses. Aid stations are spaced four to eight miles and the event is cupless with reusable cups provided at check in.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

Trail running event on October 31, 2026 at the Greenbush trail system near Glenbeulah, WI. Choose a 5K one loop or a 10K two loop course; chip timing is provided and a park sticker or daily pass is required.

A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding forest projects.

Trail runs and a walking option use a rolling park course that starts at the southwest corner and returns through woods, service road, and open sections with occasional rough footing and visible seasonal foliage.

Bucks & Does 13.1 Pointer is a multi-distance running, walking, and ruck event at Nashotah Park on 11/14/2026. Distances range from a youth Bambi Run to a 13.1 Pointer, and every finisher receives a wooden finisher medal.

The Midwest XC Championships will take place in Somers on Saturday 28 November 2026. You can run 5 kilometers.

A night out and back trail event in Lake Mills, WI offering 16 mile and 31 mile distances on a flat crushed-limestone rails to trails course with aid stations, required lights and reflectors, and finish tokens.

A winter timed ultra in Dousman, Wisconsin offering 6, 12, and 24 hour options for solo runners or relay teams of up to four, set in winter woods and on a frozen lake with warming shelters, hot drinks, a meal, and finisher items included.

A point to point trail run on the Northern Kettle Moraine Ice Age Trail in Greenbush, WI on April 3, 2027. Offers 50K and 25K distances with aid stations and transport to the start; presented as a fun run not a race.

Trailbreaker returns to Waukesha on April 4, 2027 with races from a 1K kids run to a full marathon, plus ruck options and a walk. Proceeds support the Park Foundation of Waukesha and local parks and recreation.

Paws for a Cause in Denmark WI on October 16, 2027 offers canicross and solo trail run or walk options of 2.8, 5.6, and 8.4 miles, with proceeds benefiting Crisis Cafe.