WinMan Trails

Tucked between Winchester and Manitowish Waters in Wisconsin’s Northwoods, WinMan Trails (the name blends Winchester and Manitowish Waters) has grown into one of the state’s standout four-season trail systems. What began as a small, family-driven vision in 2013 now encompasses more than 40 miles of trails for cross-country skiing, mountain biking, hiking, snowshoeing, and simply enjoying the trailhead with friends.

The system offers up to 23 km of groomed Nordic ski trails, plus 10 miles of groomed fat-bike loops and 9 miles of snowshoe routes. There is also 23+ miles of machine-sculpted singletrack for beginners through experts. Dogs are welcome on designated trails. It’s a rare Wisconsin destination where the whole family can go and everyone has something to do. The dedicated snow bike loops and marked snowshoe routes ensure that every type of adventurer has room to roam.

 Executive Director Sam Wolter often takes her three children out to the trails. “Our ski trails are mostly gentle and rolling, so they work for every level. We’ve added a new practice loop for beginners, and we offer free Nordic Rocks skis for kids and snowshoes for anyone who wants to give it a try. Our crew maintains the trails several times a week, weather permitting. Being right on the edge of the lake-effect snow belt really works in our favor. Last winter, it gave us about eight solid weeks of quality skiing. One of our favorite traditions is the Early Bird Ski Race each December that targets youth skiers.”

The trails originated from the local Gering family’s 160-acre property, and the entire project began as a few trails intended for family and friends. With subsequent land purchases, the Gering property grew to 360 acres. “The Gering Family is still an instrumental component of this organization,” according to Wolter. Today, thanks to a land use agreement with the WDNR, WinMan’s trails utilize a total of 1300 acres.

Wolter explains why WinMan works so well. “The trails are purpose-built with features that allow for progression and provide options for various skill levels. This approach accommodates both beginners and more experienced skiers and riders. This venue is ideal for families. A mountain biker in their thirties can ride alongside their six-year-old on the same trail. Riders have opportunities to tackle various features and build confidence gradually. We are also working on creating adaptive trails to enhance accessibility further.”

WinMan also offers trails and events for Onewheel, a self-balancing electric skateboard featuring a single large wheel in the center. Riders stand sideways on the board and control movement by leaning forward to accelerate and backward to slow down or stop. The device utilizes internal gyroscopes and accelerometers to maintain balance and respond to the user’s movements. Watching the Onewheels cruise the WinMan trails was impressive to this writer.

The Centerpiece

The trailhead chalet at WinMan serves as a prominent feature of the facility. This well-appointed lodge features restrooms, communal areas, a bar, and a gift shop, as well as a comfortable environment for guests to relax and warm up after participating in outdoor activities such as skiing or biking. It also regularly hosts events and community gatherings, offering a space that fosters visitor interaction. “It’s one of the few places where you can buy a craft beer for under $5,” laughed former Acting Director and volunteer Gene Oestreich. Get this- there is a Masonry fireplace that doubles as a pizza oven! Oestreich volunteers big time at WinMan and is a frequent trail user. He cherishes WinMan and the Heart of Vilas County paved trail system. “There are approximately 52 miles of scenic paved asphalt trails in the Heart of Vilas that connect St. Germain, Sayner, Bolder Junction, and Manitowish Waters. WinMan connects directly to this system.”

Wolter shared the vision for WinMan’s future direction, which involves transitioning from reliance on large donors to cultivating broader community-based support. In 2022, an on-site bar and apparel shop were established. A significant capital expansion is currently underway to add trailside cabins and campsites for our visitors. The project totals $2.7 million, with $1.3 million already raised,” according to Wolter. “We have initiatives to diversify our financial model, ensuring sustainability for years to come. Operating as a 501(c) 3 provides unique development opportunities compared to for-profit models.” Check out their up-to-date website, which highlights events and other features of the property. https://www.winmantrails.com.

The Uihlein Footprint

Amid this backdrop, Elizabeth and Richard Uihlein—best known as the founders of the shipping-supply company Uline—have invested in enhancing many of these amenities. They established a $2 million endowment to maintain the paved Manitowish Waters bike trails, and their support has extended to lodging, dining, and recreation businesses that serve both locals and visitors. Additionally, they’ve contributed to the upkeep of several town parks, ensuring that public spaces remain welcoming for both residents and visitors. From Smokey’s Supper Club to Dixie’s Coffee House, The Lodge at Manitowish Waters, a spa and salon, as well as the Manitowish Waters Athletic Club, their investments have strengthened the outdoor economy that thrives in the area. In 2015, the state approved a deal to sell them 765 feet of Rest Lake frontage adjacent to their Lodge—a local flashpoint that illustrated how private investment and public land decisions can collide in small Northwoods communities.

Local reporting over the years has chronicled both the appreciation for improved amenities—such as pavilions, paved paths, and trail maintenance endowments—and debates over process and public control. WinMan sits right in the middle of that conversation: it’s a donor-supported trail system that pairs professional operations with volunteerism, memberships, and small gifts, as much as it does with marquee donations. Their hospitality business supports the outdoor economy fueled by trails like WinMan

Economic and Community Impact

WinMan Trails has become a case study in how small towns can leverage philanthropy, nonprofit management, and smart trail design to build an outdoor asset with outsized economic and social returns. The Uihleins’ role—through the chalet donation, long-term funding for the town’s paved bike paths, and ownership of local lodging and dining establishments—has clearly amplified the region’s outdoor recreation appeal. The collaborative mix of donors, local businesses, and everyday trail users will determine how this Northwoods success story evolves.

According to a 2024 study conducted in partnership with the Wisconsin Office of Outdoor Recreation, WinMan contributes more than $4.3 million annually to the local economy, supporting lodging, dining, retail, and seasonal employment.” These findings highlight just how much visitors to WinMan support the broader Northwoods community, and we hope local and regional businesses see this impact as an opportunity to grow with us through sponsorship and partnership,” Wolter explained.

WinMan Trails has evolved into more than just a set of trails—it’s become a community centerpiece and a destination for adventure seekers across the Midwest. Whether you’re gliding through freshly groomed ski tracks on a crisp winter morning or carving down flowing singletrack in the height of summer, WinMan offers a uniquely Northwoods experience that blends nature, recreation, and community spirit.

Destination Manitowish Waters, WI - Where to Stay and Play

Manitowish Waters, Wisconsin (population 656), is a serene Northwoods town nestled in Vilas County, known for its pristine lakes, forest lands, and laid-back charm. It is a four-season destination where visitors enjoy hiking, biking, paddling, cross-country skiing, and snowshoeing.

Restaurants and lodging run the gamut. Blue Bayou Inn is one of my favorites, serving up  Cajun and Creole-inspired dishes, while Smokey’s Restaurant & Supper Club offers an upscale setting. For lakeside views, visit Dixie’s Coffee House for coffee and paninis. Pea Patch Saloon, Aurora Borealis, Aberdeen and Little Bohemia Lodge provide good casual fare. Crafters should check out the Aqualand Alehouse in nearby Boulder Junction. The Lodge at Manitowish Waters offers luxury lodging, while several motels and cabins provide a relaxed stay. Be sure to visit the North Lakeland Discovery Center and Rest Lake Park with its scenic pavilion.

Need some skis, wax, or other gear? Both Coontail and River’s Edge are reliable four-season outfitters that are likely to meet your needs. Additionally, both businesses are dedicated supporters of WinMan.

Author and publisher John Bates, a resident of Manitowish Waters for over four decades, suggests visitors take the time to explore the region. “Hike the North Lakeland Discovery Center’s loop trails—particularly the River Trail loop, which offers scenic views along the Manitowish River. Birding at Powell Marsh Wildlife Management Area can be an exceptional experience. For those seeking more remote experiences, canoe some of the area’s wild lakes, including Plunkett Lake, Sandy Beach Lake, Sherman Lake, and Mud Lake, or paddle the Trout River from Highway 51 into Wild Rice Lake.” Bates has written extensively on topics such as wild lakes, old-growth forests, and other features of the Northwoods.

Those looking for an alternative winter adventure should venture out to The Glide, a unique 0.8-mile ice skating trail in the Northern Highland-American Legion State Forest. Located near Boulder Junction, this well-maintained trail offers skaters the opportunity to glide under solar-powered lights, take breaks in a warming shelter, and gather around a bonfire pit. With Zamboni grooming ensuring prime ice conditions and complimentary skate rentals available, The Glide operates daily throughout the winter, offering an inviting way for visitors to enjoy the beauty of the Northwoods beyond traditional ski or snowshoe tracks.

The WinMan Trails are located within the Northern Highland-American Legion State Forest at 6870 Hwy W, Winchester, Wisconsin. The trail system spans about 1,300 acres and includes a mix of private and public recreation lands. The broader area is deeply embedded in state forest territory. Trails are open to the public with a suggested daily donation or annual membership, which supports maintenance and facility upkeep. The Creator Camp winning video on the WinMan website landing page gives an excellent overview of what the system offers.

https://www.winmantrails.com.

Experiencing WinMan with Volunteer Gene Osetriech

My introduction to Gene Osetriech came through an unexpected avenue. SS editor Lou Dzierzak forwarded an email from a reader who appreciated my article on Wisconsin/Upper Peninsula mountain biking but took me to task for not mentioning WinMan. I corresponded with the reader, who invited me to tour and bike WinMan, which I accepted.   Gene was a great host, and I was instantly hooked on the spectacular, flowy trail system. Gene’s insights underscored the importance of WinMan to both silent sports enthusiasts and the local community.

 Starting in 2012, Gene has poured countless hours into maintaining and enhancing the network of cross-country ski, mountain bike, and hiking trails that draw visitors throughout the year. Gene’s contributions span every season to help ensure that WinMan remains a premier destination in the Northwoods. Fellow volunteers and visitors frequently remark on his steady presence, practical expertise, and readiness to help wherever needed.

His role as a dedicated volunteer has been essential to the ongoing success of WinMan. Gene’s efforts reflect the very spirit of WinMan’s culture: reliability and humility, making a significant behind-the-scenes impact on the community. In recognition of his service, a trail was named after him—”The Gene Machine.” He downplayed his role as we biked the trails. He encourages both seasoned and new volunteers to get involved and contribute. Gene has also served as WinMan’s Acting Executive Director (ED).

ED Sam Wolter sings his praises.” Over the years, Gene has done his fair share of ski trail grooming and was instrumental in equipping the organization with ski trail grooming equipment. Gene is one of our best advocates in sharing the word about WinMan to the community. He is also a steward for The Gene Machine trail. He dedicates many hours to mowing our ski and hiking trails.”

Building Community Through Stewardship

For Gene, the trails represent more than just recreational spaces; they are places that foster community in Manitowish Waters and the Northwoods. His legacy is evident in the well-maintained trails and the culture of stewardship he helped shape, ensuring that visitors can continue to enjoy nature for years to come.

Thanks to Gene’s dedication, WinMan visitors experience some of the finest ski and bike trails in the Midwest. For Gene, the greatest reward is not recognition or accolades but knowing that others can appreciate the beauty of the Northwoods in a thoughtfully maintained environment. In many ways, Gene exemplifies the quiet heartbeat of WinMan—steady, enduring, and essential.