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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.

September 2026
Sep
20
Su

Twisted Roots

Trail Run Half Marathon Marathon
Experience the technical trails and scenic cliffs of High Cliff State Park in a marathon or half marathon trail run along the shores of Lake Winnebago.
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
Experience a point to point tour of the Northern Kettle Moraine Ice Age Trail with 25 km and 50 km routes featuring diverse forest terrain and technical trails.
July 2027
Jul
18
Su

Cliff Runner 10K

Trail Run 10 km
Experience a 10k trail run through High Cliff State Park featuring over 500 feet of elevation gain with rocks and roots across the scenic Sherwood landscape.
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.
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