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Business of the Month: September 2023

WinMan Trails



WinMan House

Main Trailhead:
6870 County Highway W.
Winchester, WI  54557

Website: WinManTrails.com

Email: [email protected]

Phone: (646) 543-8784

It was a pleasure recently to spend some time with Isaac Cowart, Director of Operations, WinMan Trails Foundation, to learn about their fabulous 40+ miles of trails in Vilas County spanning 1,300 acres!  Connected to the Heart of Vilas Trail System, WinMan is on track to exceed 45,000 visits this year. Isaac was pleased to submit the following narrative sharing the WinMan story.

WinMan is a non-profit that exists to foster a healthy outdoor environment where all our community members can grow stronger, together. Located in Winchester, Wisconsin we’re a free facility and open year-round for visitors to enjoy. 

Founded in 2013, the original trails were built on privately owned land by Susie and Rick Gering. The Gering’s had a vision to enhance the area by providing opportunities for more people to enjoy the Northwoods. In 2018, WinMan expanded thanks to a DNR Land Use Agreement. Currently, WinMan manages 40+ miles of trails spanning 1,300 acres.

Through four full-time staff, hundreds of volunteer hours, and a community of engaged users who help promote and advocate for the trails, WinMan continues to grow, evolve, and excel at giving users an exceptional outdoor trail-related experience. 

WinMan is conveniently located on the Heart of Vilas Paved Trail System. This allows groups to gather at WinMan with certain riders choosing asphalt while others can explore the dirt.

We offer challenging trails and features for advanced users, but we are also intentionally geared towards beginners and intermediate-level users. The result is a trail system that meets the needs of everyone while still providing opportunities to improve one’s abilities.

In the summer we offer 23+ miles of mountain biking, a skills park and pump track, and six miles of hiking. In the winter we have 22 kilometers of groomed classic and skate cross country skiing, 3 kilometers of backcountry skiing, 10+ miles of fat tire biking, 8+ miles of snowshoeing, and a sledding hill.

In addition to amazing trails, we offer numerous amenities including a heated chalet, outdoor shaded gathering spaces, bike wash, ski waxing bench, indoor restrooms, fire pits and a bar and apparel shop. This combination of “wildness and comfort” allows multiple generations to enjoy WinMan together.

The growth and success of our trail system, as well as other attractions regionally, draws significant tourism to the area. We are on pace to exceed 45,000 visits this year. Surveys over the years have found that 80% of visitors come from more than 25 miles away and in the summer months, 52% of visitors are visiting the region specifically because of WinMan. We continue to experience consistent year over year growth from outdoor enthusiasts seeking quality snow conditions or an enhanced mountain bike experience.

As we celebrate our 10-year anniversary, we continue to look ahead. We are exploring some great opportunities to meet the future needs of visitors. As a non-profit, donations are encouraged to help us meet those needs as 100% of our trail development and facility maintenance is supported by contributions from our users and community. 

From expanded trails to new amenities, you can always expect something new when you visit WinMan. We extend our gratitude to the VCEDC and everyone for their support!

Congratulations!!



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