Explore the Northwoods: The Best Hiking Trails for Every Skill Level

Easy Does It: Family-Friendly Adventures 

Bearskin State Trail 

Sometimes the best adventures happen at a leisurely pace. This converted railway spans 21.5 miles of gentle terrain that's perfect for the whole crew — strollers, grandparents and curious kids included. The crushed granite surface makes for easy walking, and cool trestle bridges and towering pines will have everyone wandering in wonder. First-timer tip: Start at the downtown Minocqua trailhead and walk as far as your youngest hiker's legs will take you. 

Step It Up: Moderate Trails That Deliver

Madeline Lake Trail

Ready to earn those views? This network of four loops — mix and match your own up to 16.5 miles — takes you through mixed hardwood forests that practically glow during peak fall color. The trails wind in between pristine lakes where you can catch your breath and soak in reflections that look like watercolor paintings. It's challenging enough to feel accomplished but gentle enough that you'll still have energy for s'mores later. 

Minocqua Winter Park Trails 

Don't let the name fool you — the Minocqua Winter Park Trails shine in autumn, too. With multiple loop options ranging from 1 to 5 miles, you can customize your adventure based on how your legs are feeling. The varied terrain keeps things interesting, and the hardwood ridges offer glimpses of the lake country that make this region so special. First-timer tip: Don’t miss the Squirrel Hill Overlook. It’s steep but paved and stroller-friendly.  

Bring Your A-Game: Challenging Hikes 

Hidden Lake Trail 

Ready for a true wilderness adventure? This trail loops around Butternut Lake, in the Chequamegon-Nicolet National Forest, and offers the ultimate Northwoods experience — including the option to camp overnight by a remote lake if you're feeling ambitious. The trail winds past several scenic vistas and leads you through a remarkable stand of ancient hemlocks that'll make you feel like you've stepped back in time. Definitely grab a trail map before you head out, since this up-to-13-mile adventure mazes across old roads and other trails. 

Lumberjack-Escanaba Trails 

These 11 miles are where avid hikers come to play. Winding along the scenic Manitowish River and around White Sand and Escanaba Lakes, these trails offer everything from gentle waterfront terrain to challenging hills. You'll pass through multiple worlds, from old timber stands to wetlands and pristine lakeshores. Best yet, backpack camping is allowed with a permit for a multi-day getaway.  

Make the Most of Your Wisconsin Adventure 

Fall hiking in Wisconsin means layers are your friend; mornings might be crisp, while afternoons warm up beautifully. Pack water and snacks, because fresh air has a way of working up an appetite. And don't forget that camera, though no photo quite captures the magic of the Northwoods’ stillness — minus your boots crunching through those autumn leaves.