Wisconsin Cycling: How to Sightsee the Driftless on Two Wheels

Cycling and Sightseeing in Driftless Wisconsin

Fall is truly a special season in Southwestern Wisconsin. Along the scenic byways of rolling bluffs and winding roads, the vivid colors emerge as leaves begin to change. The only problem? There is so much natural beauty in our state’s Driftless Region that it’s tough to see it all. Wisconsin cycling and mountain biking, however, is the perfect solution – allowing you to cover more ground and explore the enchanting autumn colors like never before!

Ready to hop on two wheels and give it a try? Here are a few of the best Wisconsin cycling and mountain biking routes near Boscobel, in the heart of the Driftless region:

Sidie Hollow - Lake Loop
Photo by M James Reuter

Sidie Hollow County Park – (Viroqua, WI)

Loop Length: 11-mile (single track) trail network
Two-Wheeled Activities: Mountain Biking, Fat Tire Biking

With a well-groomed network – maintained by Vernon Trails – these beautiful, scenic loops feature lake views and rolling bluffs. An ideal setting for a ride in the woods, the majestic autumn colors are abundant along these trails. Sidie Hollow also serves up great fat tire bike routes come wintertime.

Kickapoo Valley Reserve
Photo by Kickapoo Valley Reserve

Kickapoo Valley Reserve Loops – (La Farge, WI)

Loop Length: 25-miles of varied trail types
Two-Wheeled Activities: Mountain Biking, Cycling, Fat Tire Biking

The Kickapoo Valley Reserve includes 8,600 acres of land between La Farge and Ontario, Wisconsin. Fall colors abound in the area, gently lining sandstone outcroppings and surrounding the various paved and off-road trails. Let your mind wander, while you enjoy the native flora & fauna on this serene autumn adventure.

The River Loop - Boscobel, Wisconsin Cycling

The River Loop – (Boscobel, WI)

Loop Length: 18-miles
Two-Wheeled Activities: Cycling

This fairly short bike route between Boscobel and Blue River is mostly flat and perfect for beginners or kids. However, it’s also paved with breathtaking surroundings making it perfect for Wisconsin cycling. Enjoy a crisp autumn breeze through a quaint, colorful countryside that offers pleasant river views throughout this mesmerizing ride.

Castle Rock Cycling Loop

Castle Rock Loop – (Fennimore, WI)

Loop Length: 30-miles
Two-Wheeled Activities: Cycling

Follow the path of scenic Hwy 61 on a wide, paved shoulder which follows rolling hills and historic rural landscapes. You’ll also experience plenty of wildlife along the way, as this route winds close to the banks of the Blue River and a rippling class-1 trout stream. Don’t be surprised if you spot a soaring bald eagle or bumbling wild turkey, as you cruise through the changing leaves.

Morrey Creek Cycling Loop
Photo by Wisconsin DNR

Morrey Creek Loop – (Muscoda, WI)

Loop Length: 38-miles
Two-Wheeled Activities: Cycling

Experience incredible landscapes and wildlife through a dreamland of Fall colors. This route features some difficult climbs, but the exceptional bluff and river overlooks more than reward your efforts. You’ll also bear witness to several historic country churches nestled into the Driftless scenery.

Wyalusing Bike Loop
Photo by Friends of Wyalusing State Park

Wyalusing Bike Loops – (Wyalusing State Park)

Loop Length: 51-miles
Two-Wheeled Activities: Mountain Biking

At the confluence of the Wisconsin and Mississippi Rivers, you’ll bike through hardwood forest, wetlands, bluffs, springs, and backwater terrain at Wyalusing State Park. As you explore the vivid oranges, yellows, and reds of Fall, expect a terrific mixture of rises and falls on these trails. You may even spot a waterfall or two, adding elegance to an already brilliant autumn adventure.

Cycling and Sightseeing Boscobel, Wisconsin

Wisconsin Cycling and Sightseeing in the Driftless Region

Well, what are you waiting for? Gather up some friends or family, and come out to explore the Driftless Region – Wisconsin’s best kept secret for outdoor recreation!

There are so many incredible ways to enjoy the enchanting Fall colors, and allow the stresses of daily life to simply melt away. Learn the best ways to enjoy an autumn getaway in Boscobel – Wisconsin’s Outdoor Recreation Destination.