A Mountain Biker’s Guide to WinMan Trails in Wisconsin: Tips for First-Time Visitors.

WinMan Trails entrance sign near Winchester, Wisconsin

I love riding at WinMan, especially as an intermediate rider looking to explore new challenges. My first trip was guided, as I was there for coaching, but on my second visit, I explored the trails on my own, riding them over and over again. There’s still one trail I haven’t ridden, but every trip has helped me better understand the terrain.

While I’ve already written a detailed review of the WinMan trails, this blog focuses on my personal experience with each one. I’ll also share my recommendations for what’s best to ride for beginners, intermediates, and anyone getting started on these incredible trails.

Finding WinMan Trails in Northern Wisconsin.

WinMan Trails are nestled in the beautiful Northwoods of northern Wisconsin, just outside Winchester. Whether planning a day trip or a weekend getaway, the trails are easily accessible from several major cities in the region.

• Address: 6870 County Hwy W, Winchester, WI 54557

• Distance from Major Cities:

  • Wausau, WI: ~95 miles (approx. 1 hour 45 minutes)

  • Green Bay, WI: ~170 miles (approx. 3 hours)

  • Madison, WI: ~230 miles (approx. 4 hours)

  • Milwaukee, WI: ~270 miles (approx. 4.5 hours)

  • Minneapolis, MN: ~240 miles (approx. 4 hours 15 minutes)

  • Chicago, IL: ~350 miles (approx. 6 hours)

Driving Directions: From Minocqua, head north on WI-47 and turn onto County Hwy W. Follow Hwy W for approximately 20 minutes; the trailhead will be on your right, marked by signage and ample parking.

What Makes WinMan Trails in Wisconsin Special for Mountain Bikers?

For me, what makes WinMan Trails in northern Wisconsin special is the thoughtful design of each trail. There are many types, with one common feature: unique rock gardens.

Another highlight is the chalet—a welcoming space to change, relax, or even work with excellent Wi-Fi. With snacks, local brews, and a friendly community of fellow riders, the vibe at WinMan is second to none.

Map of WinMan Trails with labeled mountain biking routes and difficulty levels.

Pro Tip: Get the Trailforks app before heading to WinMan Trails. Trailforks offers detailed maps, trail descriptions, and live trail conditions, helping you navigate more easily and discover new routes based on your skill level. It’s an invaluable tool for exploring WinMan’s network and staying informed on any trail updates.

Best Trails to Start Your Day at WinMan Trails.

Start your day with a warm-up on Scout. It is the first trail to the left of it all and is a beginner-friendly route that provides a good indication of what’s to come, with rollers and rock features set up for a great warm-up. This trail is green and short, 0.5 miles, and long, 1 mile.

After you’ve warmed up on Scout, head to WinMan One. This beginner-friendly, flowy, 2.1-mile green trail offers great options to take it up a notch. It passes through the Front Hub, but don’t get distracted by all the excitement—stick with WinMan One for now, and we’ll return to the Front Hub later for all the fun it offers.

Map showing only Scout and WinMan One trails

Trails to Explore After Warming Up at WinMan.

Front Hub sign in the fall with a spinning wheel to help riders choose their next trail.

Now that your warm-up is complete, take Earn It to the Front Hub. Earn It gets its name from the climb; be it short, it is still a climb. Earn It is the fastest route to the Front Hub. The Front Hub is a center point connecting you to seven trails. I would try all of these. Most are short and take you back to the Chalet, where you can take Earn It back up each time and try another. I recommend having fun here after your warm-up. The trails are:

Map showing the starting points of trails from the Front Hub (10).

Start of Bridge trail in a forest during fall, featuring an up-and-over bridge and the trail sign.

1. Bridge: I have to admit the name Bridge was a little intimidating. But do not fear. It is very ridable. This is a .75-mile blue trail. The trail begins with an up-and-over bridge, setting the tone for the following technical wooden features. You have a berm leading to a rock jump/roll feature right after that. From there, you will have a few more wooden features, from skinny ones to wooden bridges. The Bridge is a trail I enjoy riding with its tech, wooden features, and flow.

2. Glacial Erratic: This trail is awesome. It is the newest trail at WinMan. Known for its constant twists and rocky features, Glacial Erratic is a 2-kilometer trail with a mix of short climbs and descents. The rock gardens here will give you a taste of WinMan’s signature rocky terrain. Although this trail is blue, it could easily be considered black in some sections.

3. Roller Creek: Roller Creek is fast with flow and sweeping turns. It is an excellent choice for riders looking to build momentum without too much technical demand. Known for its smooth, flowing path, Roller Creek offers a fun ride for beginners and seasoned bikers, allowing riders to practice speed control and cornering.

4. Send It: True to its name, Send It is designed for those looking to tackle jumps and drops with a bit of flair. This trail combines flowing segments with technical jumps and features that cater to intermediate and advanced riders.

5. Air Mail: Air Mail is all about airtime and precision. This trail is crafted with a series of jumps that range from small to larger senders, ideal for those who enjoy flight and are comfortable landing with control. Air Mail is an exciting, skill-focused trail suited for intermediate and advanced riders who want to perfect their jump technique.

6. Twins: This unique trail has dual slalom lanes, providing a fun, side-by-side riding experience. Each line has varied features, including turns and small jumps, making it an excellent choice for a friendly race or a chance to test handling skills on two different paths.

7. Red Trail: The Red Trail is a shorter, technical trail with many rock features and bermed corners. It is ideal for intermediate and advanced riders looking to practice control on technical terrain. The rocky elements and berms make Red Trail a go-to for honing skills on more intricate features.

Pro Tip: If you are not at the intermediate/advanced level, you might want to bypass Red Trail, Air Mail, and Send It.

Start of the Red Trail with a sign reading 'STOP: Expert Riders Only.

After you ride these, you can always come back for more later. Or, continue.

Trails to Complete Your Ride at WinMan Trails in Wisconsin.

Your legs are probably starting to feel tired, but this last set is super fun. So, grab a Coke and snack from the Chalet to fuel up.

Map showing the final route of trails at WinMan.

In this last set, take WinMan One from the start at the Chalet base. You will come to a fork in the trail. Straight continues Winman One, which you have done. This time, take the left to Flowage. Get your flow on this trail with berms, rollers, and more berms. The flowage is blue at 1.7 miles of ups and downs. At the bottom of Flowage, you will be at base 20. At base 20 is one of my favorite trails, Lake Trail. It is a short, old-school, narrow trail with many crunches and roots. It will loop back around to the start. I can ride this trail over and over again. Love Lake Trail.

Next, take Perimeter Trail to Rear Hub (23). At 3.79 miles, the Perimeter Trail is the longest trail at WinMan. It is more old-school cross-country style. The Rear Hub has many awesome trails. From here, take Gene Machine. People love Gene Machine. Gene Machine offers a/b lines for you to choose from based on your skill level. It is a smooth-flowing trail with jump options—Gene Machine loops to the Rear Hub, where you take Lambo Spur to the Bottom Bracket and then onto Roller Coaster that will roll you back into home base.

That is a fun loop with a lot of different trails that each have their flavor.

Pro Tip: If you are not at the intermediate/advanced level, you might want to bypass Gene Machine and take Lambo Spur.

Trail Breakdown: Highlights of each trail.

While I've shared my personal favorites and recommendations for first-time visitors, here’s a complete guide to all the trails at WinMan. Each description provides a quick overview so you know exactly what to expect

• Scout (Green, 0.5 miles): A beginner-friendly trail perfect for warming up, featuring gentle rollers and a smooth flow to build confidence.

• WinMan One (Green, 2 miles): A flowy trail with smooth terrain and moderate turns, designed for riders of all levels looking for a fun, steady ride.

• Bridge Trail (Blue, 0.6 miles): Known for its wooden features, including narrow bridges and some rock elements, this trail tests balance and precision.

• Glacial Erratic (Blue, 1 mile): This intermediate trail weaves through rocky features and twists, offering a technical challenge for riders ready for varied terrain. Watch our YouTube video, Intermediate MTB Rider Tackles Glacial Erratic Trail for the First Time for a closer look.

• Roller Creek (Blue, 2 miles): A fast, flowing trail with gentle downhill sections and sweeping turns, providing a smooth, enjoyable ride.

• Flowage (Blue, 1.7 miles): This trail is packed with berms, rollers, and flowy sections, making it an exhilarating ride for intermediate riders seeking a dynamic mix of speed and control. Watch our YouTube video, Flowage Trail at WinMan Trails, Wisconsin: A Must-Ride MTB Experience for a closer look.

• Perimeter Trail (Blue, 3 miles): A scenic loop around the trail system, offering moderate climbs and descents, great for a longer, steady ride.

• Lake Trail (Blue, 0.5 miles): A classic, narrow single track with roots, crunch, and rock features. This old-school trail offers a raw, rugged ride for intermediate riders. Watch our YouTube video, Lake Trail at WinMan: Old-School Single Track MTB Ride in Wisconsin for a closer look.

• LAMBO Spur (Blue, 1 mile): A flowy trail with natural rock features and smooth paths, perfect for intermediate riders seeking a blend of flow and technical elements.

• Gene Machine (Blue/Black, 0.8 miles): Featuring optional jumps and technical lines, this trail provides an exciting, varied ride for advanced riders.

• Send It (Black, 0.5 miles): True to its name, this trail is loaded with jumps and technical features, making it a favorite for riders eager for some airtime.

• Air Mail (Black, 0.5 miles): A jump-focused trail with a series of well-spaced jumps, perfect for riders working on control and airtime.

• Twins (Blue, 0.3 miles): A dual slalom trail, allowing riders to choose between two lanes for side-by-side friendly competition with turns and small jumps.

• Red Trail (Black, 0.4 miles): This trail is short but technical, featuring rock gardens, tight turns, and berms. It is ideal for intermediate riders honing their skills.

My top five trails at WinMan.

This list may change as I develop better skills and eventually learn to catch air.

Coach Brenda tackling the emphasis rock garden at the end of Red Trail.

1. Lake Trail: I love old-school trails. This trail is just that, with lots of crunch, roots, and rock features on a skinny single track.

2. Red Trail: What I like about Red Trail is the rock gardens. And, near the end of the trail, it gets super old-school with a skinny, crunchy path that’s fun to ride with a giant rock garden to end your ride if you dare to ride the garden.

3. Glacial Erratic: This trail is set in a gorgeous park, and I eat that stuff up. As a ride, it’s a lot of fun with technical rock features and a nice flow.

4. Roller Coaster: I love how fast and flowy this one is. It’s all about speed and smooth turns.

5. Send It (although I can’t jump…yet): Just so much fun. It’s downhill, and even without jumps, it’s a blast.

The best times to visit WinMan Trails.

WinMan Trails offers unique experiences year-round. Spring brings cooler temperatures and quiet trails, though early mud may cause closures, so check trail status. Summer is peak season, with lush scenery—ride in the morning or late afternoon to beat the heat and crowds. Fall is ideal for mild weather, vibrant foliage, and great trail conditions, especially on weekdays. Winter offers fat biking on groomed snow trails; check conditions for snowfall updates.

Ready to Ride? Final Tips for WinMan Trails.

WinMan is a great place to improve your mountain bike skills. There are many trail options with different features, and they even have a skills park. I love this place, and I hope to see you there. Happy trails.

Have you visited WinMan Trails? Share your favorite trail or tip for first-time visitors in the comments below.

To learn more about WinMan Trails, click the button below to visit their official website.

Check Out Our Other Content on WinMan Trails.

YouTube video: Flowage Trail at WinMan Trails, Wisconsin: A Must-Ride MTB Experience.

YouTube video: Lake Trail at WinMan: Old-School Single Track MTB Ride in Wisconsin

YouTube video: Intermediate MTB Skills for Women: WinMan Trails Adventure in Wisconsin

YouTube video: Intermediate MTB Rider Tackles Glacial Erratic Trail for the First Time | WinMan Trails, Wisconsin

Trail Review: WinMan Trails in Wisconsin.