This elegantly-crafted trail system in Wisconsin boasts 5 full-time staff members

Winchester, Wisconsin, has a population of roughly 500 permanent residents and over 3,000 seasonal residents. Those who visit it are drawn to its recreational opportunities: Winchester has nearly 60 lakes and over 6,000 acres of public land.

And now, mountain bike trails are one of Winchester’s biggest draws.

Over 1,300 acres of Winchester’s public land is occupied by the WinMan Trails, a year-round multi-sport trail system that offers 23+ miles of singletrack. Best of all, it’s a free public trail system that’s managed by a non-profit organization that strives to provide high-quality outdoor adventure opportunities to its users.

To find out more, Singletracks spoke to Isaac Cowart, the Executive Director of WinMan Trails, Inc., the 501(c)3 non-profit organization that manages the trails; Jeremy Johnson and Joel Kleimola, the two full-time trail builders WinMan has on staff; and Rick Gering, the man whose idea of building trails on family land led to the creation of the WinMan Trails.

Originally, Gering decided to build a few miles of trails for his family and friends to enjoy.

In the early 2010s, Gering, who had recently retired, decided to purchase 160 acres for himself and his son to hunt on. Before long, he and his family also started using the land for snowshoeing and skiing during the winter months.

Then, Gering bought a mountain bike and started pedaling the logging roads on the property. That led to the idea of building mountain bike trails since both Gering’s son and daughter enjoyed riding, too.

Gering reached out to a friend in nearby Minocqua to see if he knew anyone who could build trails. That friend put him in touch with Travis Bellman, a trail builder who had been working on the Raven Trail in Minocqua. Bellman, along with Gering, Robert Polic, and Gene Oestreich, built a short demonstration loop using a mini-excavator. These trails, possibly the first machine-built trails in Wisconsin according to both Cowart and Gering, were different from any trails that existed at the time.

Within a few years, Gering had expanded his vision, and the concept of the WinMan Trails was born.

As Gering puts it, “We were just building trails and having fun.” So much fun, in fact, that Gering purchased another 200 acres of adjacent property with a parking lot that became the trailhead. Gering decided to keep building trails to show others what was possible, and people began traveling there to ride.  

WinMan, whose name is derived from its location between the towns of Winchester and Manitowish Waters, first opened its trails to the public in 2013. In just two short years, the popularity of the trails grew quickly. This led to the creation of WinMan Trails, Inc., a non-profit organization that manages the land and all future trail building and maintenance projects on the property. The organization currently has five full-time staff members, including Cowart, Johnson, and Kleimola, as well as Sam Wolter, the Director of Community Engagement, and Brad Kusz, the Property Manager.

A land-use agreement gave WinMan access to even more land for trails.

Shortly after WinMan Trails, Inc. was formed, the Wisconsin Department of Natural Resources (DNR) bought a large parcel of land next to the property. Gering quickly realized that the DNR land had great terrain for trails. As a bonus, the DNR forest director liked what WinMan was doing and appreciated the sustainability of the trails Bellman had built. 

WinMan Trails, Inc. and the DNR worked out a land-use agreement in 2018 that gave WinMan access to almost 1,000 more acres of land. Today, WinMan has five distinct trail systems, including 23 miles of machine-built, one-way mountain bike trails, 10 miles of groomed fat bike trails, 13 miles of cross-country ski trails, nine miles of snowshoeing, seven miles of hiking and trail running, a skills park and pump track, and a sledding hill.

WinMan’s in-house trail builders have created some amazing singletrack.

The area in which the WinMan Trails are located is unique, according to Cowart. There is only 105 feet of vertical elevation in the area, and the land itself can differ dramatically depending on the location. “The area where we are located was formed by glaciers over 5,000 years ago. Four miles away from us is sandy soil, but the unique topography where WinMan is situated provides as close to loamy soil as you can find.”

Johnson and Kleimola, WinMan’s in-house trail builders, have taken full advantage of the park’s topography to build some amazing trails. Johnson said that all the people who work on WinMan’s trails “are a group of friends who ride together. The passion is huge with the people we have here, and it shows in the quality of our trails.”

Unlike contracted trail builders, who often build trails to client-driven specifications, Johnson and Kleimola build trails based on what they like to ride and what the riders at WinMan say they want to ride. Johnson said that building trails in one location has forced them to broaden their styles. “We try to change up the size and shape of things” to make sure there are noticeable differences among all the trails.

For Johnson and Kleimola, who both worked for contracted trail builders before joining WinMan’s staff, there is a lot of satisfaction in the work they do because they get to see the results of it first-hand and get real-time feedback from the riders who use their trails. That feedback allows them to immediately fix and make changes to a trail when needed and ensures WinMan provides its visitors with the highest-quality trails possible.

Cowart describes WinMan as a feature-rich trail system with over 150 unique trail features, all having ride arounds. According to Cowart, WinMan frames itself as a place where the whole family can ride the trails together and have a good time regardless of their experience level. Additionally, he said that having full-time trail builders on staff means “there is always something new or improved every time you visit.”

The WinMan Trails are a major contributor to the region’s economy, and it is only getting bigger.

WinMan Trails has come a long way since its humble beginnings as a family playground. To date, $4.6 million has been invested in the park to make it a year-round outdoor recreation destination. That investment is paying off. A recent economic impact study found that there will be over 55,000 visits to the park by the end of 2024 and it will add over $4 million to the local economy by year’s end.  

But there is still more to come. WinMan Trails will be launching WinMan BaseCamp in 2025, offering on-site camping for both tents and RVs, tiny and large cabins for lodging, a bathhouse with showers and saunas, and community spaces. Both Cowart and Gering hope this project will encourage more visitors to stay overnight in the area.

WinMan’s trail builders will also have full summer calendars in 2025. They will build new trails connecting WinMan’s new BaseCamp to its existing trail system, resurface some of the older trails, and address drainage issues. They also hope to complete a gravity-focused downhill trail with larger features geared toward enduro-style riders.

Gering hopes WinMan will continue to provide free outdoor fun for generations to come.

When asked if he was surprised by the growth of WinMan since its inception, Gering was quick to say no. “The leadership from our staff and the support from our community and our donors has allowed WinMan to be so successful in such a short amount of time.”

To provide a great riding experience at no charge to its guests, WinMan fully relies on donations and other forms of revenue. Cowart says it has both sponsors and donors and does regular fundraising as well as holding events at the park. Cowart also mentioned that the park has a bar and apparel shop that generate income, too.

Gering said that WinMan’s future is bound only by donations. As long as people continue to financially support WinMan, it will continue to grow and keep providing free outdoor recreation in an area of pristine natural beauty.