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Trail Running Calendar near Sherwood 2026-2027

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Explore the top trail runs near Sherwood for 2026-2027! We've gathered 8 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
14-15
Fr - Sa

Mike Ariens Run/Walk

Road Race Trail Run Walk 5 km 10 km
A community run/walk in Brillion honoring Mike Ariens, featuring 10K, 5K and a Kids 1K on trails and downtown routes, with finish-line ice cream, commemorative bucket hats, medals, and shuttle service between venues.
September 2026
Sep
12
Sa

Trek the Creek 5K

Trail Run Walk 5 km
A USATF certified chip timed family 5K run and walk through Pla-Mor Park and the Devil's River State Recreational Trail in Francis Creek, WI. The event includes a virtual option and proceeds support local first responders and community programs.
Sep
20
Su

Twisted Roots

Trail Run Half Marathon Marathon
Trail marathon and half marathon at High Cliff State Park on September 20, 2026, featuring technical singletrack, lake views, cupless support, and ages 16 and up.
October 2026
Oct
11
Su

Glacial Trail 50

Trail Run 50 km 50 mi
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.
Oct
31
Sa

Greenbush Trick or Trail 10K

Trail Run 5 km 10 km
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.
April 2027
Apr
3
Sa

NK50k

Trail Run 25 km 50 km
Point-to-point trail run on the Northern Kettle Moraine Ice Age Trail near Greenbush, WI, with 50K and 25K options, aid stations, and post-run refreshments.
July 2027
Jul
18
Su

Cliff Runner 10K

Trail Run Walk 10 km
A 10 km trail race at High Cliff State Park near Sherwood WI featuring single-track terrain, rocky sections and over 500 feet of elevation gain.
October 2027
Oct
16
Sa

First Annual Paws for a Cause Canicross & Trail Run/Walk for Charity

Trail Run Walk 3 mi 6 mi 8 mi
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.
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