Inspiring Adventure. Strengthening Community.

Help us grow and refine WinMan's premier, four-season, trail system and develop unique facilities that allow our community to spend more time - outside and together.

  • $500,000 Goal

During the past few years we've witnessed a tremendous influx of visitation which has opened our eyes to the need for more outdoor recreation outlets that promote a healthy, active lifestyle for the entire family.

WinMan Trails provides a distinct combination of “wild-ness and comfort” that is truly authentic.

From our rolling topography, perfect soil conditions, and sprawling hardwood forests...To our upscale amenities, ideal location in the Northwoods of Wisconsin, and one-way trails...

You will always be able to enjoy the solitude of nature without trail crowding.

We are ready to continue our sustained growth while focusing on what has always made WinMan Trails standout - quality.

  • Quality Facilities
  • Quality Amenities
  • Quality Staff
  • And most importantly - Quality Trails 


Learn How Your Contributions Are Making an Impact!

Summer Trails

    • Implementation of an innovative Hub design for improved navigation and customized riding experiences
      • New Front Hub: 10 trails merge creating 8 different trail options
      • New Rear Hub: 4 trails merge creating 3 different trail options
      • New Rear Hub Return, returning you to the Rear Hub to start a new adventure
      • New Front Hub Return, returning you to the Front Hub allowing you 8 options to keep your ride going or take you back to the chalet
    • Improved signage system wide
    • New Skills Park with 11 built-in-house steel and wooden features and 5 progressive jump lines to build your skills and have more Weeeeeee
    • Bridge Trail overhaul with 8 brand new wooden features 
    • Rerouted and improved the end of WinMan One and Roller Creek
    • Built Air Mail, one of our fastest and most challenging trails to date
    • Added skills sections to “Short Scout” making it fun for all riders
    • Added a new half-mile (and super fun) loop to create “Long Scout” 
    • Enhancements made on many trails including our expert trails, High Five and Red Trail
    • New bridge feature on Red Trail now takes you safely over Twins (and provides a great view for our snowshoers, too)

Winter Trails

    • Improved signage system wide
    • New 1.6k Beginner Ski Loop
    • New Warm-Up trail completed and ready for the upcoming season
    • New and improved Sledding Hill
    • Introduced Nordic Rocks program offering FREE classic skis for kids to use while at WinMan
    • Enhanced frequency and quality of grooming with new equipment and additional staff
    • System-wide enhancements to the ski trails with brush clearing and leveling to improve ski quality
    • Nordic Pulse GPS for grooming updates in real time
    • New trail cam for a live look at trail conditions
    • Warming hut for small groups to enjoy a snack or warm fire while out on the trails
    • Additional 1 mile of fat tire bike trails
    • Created a new section on WinMan Passage snowshoe trail 
    • Added a new trail connecting WinMan Passage to Lake Loop
    • Expanded our backcountry cross-country ski trail system with almost 3k of flagged and cleared trail to enjoy


    • WinMan Park
      • Improved layout with direct entry from the parking lot and a more accessible kiosk
      • Moved the bike maintenance hub to the main kiosk in order to ease congestion near the chalet
      • Developed spaces for families, groups and individuals to relax 
      • Installed custom shade sails, a hammock village, nature playspace, and rock wall seating area
      • Added outdoor seating and fire pits with gravel to cut down on the dust
      • Installed a sound and PA system for music and special events
      • Built new bike racks to securely hang your bikes when taking a break
      • New bike fix station and expanded tools for you to borrow
    • Chalet improvements 
      • New and improved indoor seating
      • Added storage cubbies and coat hooks
      • Updated the Bar and Apparel Shop and expanded hours through the help of volunteers
      • Expanded our product offerings
    • Parking Lot
      • Expanded to 100+ spots at the main trailhead
      • Installed vault toilets to reduce congestion in the chalet and make it more convenient to get you out on the trails

Two Ways to Make a Difference

Trailhead Concept

Fundraising Campaign

Help us meet our goal of $500,000.

More than a trailhead, we envision becoming a community hub of healthy, outdoor activity that truly characterizes our shared Northwoods character.

Scroll down for details about the projects we have planned.

Become a Member

Your membership to WinMan Trails will go directly towards supporting one of the premier trail systems in the Midwest.

Your annual commitment will allow us to fund operational needs as well as our efforts to improve and expand our trail system. Hooray, More Trails!

Learn more about the benefits of membership and how your involvement will positively impact WinMan Trails.

Membership Sticker 2023-24

- Our Vision -

WinMan Trails serves as a year-round adventure park and community gathering space for residents and visitors to experience outstanding trails and upscale facilities that inspire active, outdoor lifestyles.

Em Meier 8
  • Expand our trail mileage and improve the quality of our current trails
  • Refine our trail system with a hub design and directional trails so that users can enjoy the solitude of nature without trail crowding
  • Redevelop parts of our trail system and add wayfinding elements to make navigation more intuitive
  • Enhance our maintenance capacity to keep the trails expertly groomed and maintained year-round
  • Develop additional gathering sites such as small pavilions and warming huts throughout the property
  • Build an easy, kid-friendly ski trail
firepit (1)
  • Create more inviting community spaces at our trailhead with shade structures, picnic and lounge areas, fire pits and breezy, comfortable spaces to gather with friends and family
  • Add a space for outdoor events and live music
  • Develop more outdoor play opportunities through a nature-based play space and a sledding hill
  • Create more opportunities for all levels of riders to become better
    • Rebuilding and improving our pump track
    • Installing features to allow for progressive skill development
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WinMan Trails personifies the Northwoods outdoor lifestyle. From its humble beginning in 2013, to our current 40+ miles of unique trails, WinMan has become a favorite destination for locals and visitors who love to bike, ski, hike, and snowshoe. 

That is why we're dedicated to expanding and refining this premier, 4-season trail system. With a focus on building new trails, new trail features, and functional engaging gathering spaces, WinMan will become more than a just an amazing trail system.

Check out the slides below to learn more about our Fundraising Campaign. You can find a link to the entire slideshow at the bottom of this page.

Special Thanks to Windmill Media and The Dusty Dutchman!

Click the links above to check out all his great work and videos on YouTube.

We Need Your Help to Realize This Innovative Vision for WinMan Trails

Support of WinMan Trails

WinMan Trails is an asset to the Town of Winchester because it provides high quality, year-round, family-friendly recreation. The positive impacts it has for our residents and community are healthy outdoor activity and an expanding economic development run by professionals. The Town Board fully supports WinMan Trails and their mission, and we will continue to support their efforts moving forward in whatever way possible.

Town of Winchester
Town Board

This all-season outdoor recreational park is such an amazing gift to the area - from mountain bike trails in the summer to ski, snowshoe, and fat tire bike trails in the winter, it has everything you need to get outdoors. If you're a silent sport enthusiast, or just someone who loves to recreate outdoors, this is the place to be. The trails are great. The lodge is great. But most importantly, the community of outdoor enthusiasts is great. You will not be disappointed with a trip to WinMan. It is always time well spent.

Kristi Waits and Thomas Ponik
aka Wainik's World

One of the best trail systems I’ve been on, especially for the size. Very well made trails, super fun and flowy, and BEAUTIFUL! Very grateful for all the work that has been put into creating and maintaining these pristine trails and excited for the next phase coming. Thank you all out there who have brought this to the community.

Alyson Dudek

We Need Your Help to Realize This Innovative Vision for WinMan Trails