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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 7 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

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.
November 2026
Nov
7-8
Sa - Su

Run Til You Snowdrop-24 Hour Treadmill Run

Backyard Ultra
24 hour treadmill event by the Snowdrop Foundation at Crunch Fitness in Appleton honoring children on the H.O.T. unit and supporting families affected by pediatric cancer.
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 in Greenbush WI, with 50K and 25K options, aid stations and transport from finish to start.
July 2027
Jul
18
Su

Cliff Runner 10K

Trail Run 10 km
A 10K trail race at High Cliff State Park on July 18, 2027, featuring rocky, rooty terrain and over 500 feet of climbing, with registration that includes a T shirt and a medal.
October 2027
Oct
16
Sa

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

Trail Run 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.
Oct
23
Sa

Mosquito Hill Endurance Run

Trail Run Backyard Ultra 5 km
Trail endurance event at Mosquito Hill Nature Center in October 2027 offering 12 hour, 6 hour, 3 hour formats and a flexible 5k on a 3.4 mile loop.
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