Road

We create free-to-you routes that explore county highways and back roads in the Driftless region of Wisconsin and Minnesota. Choose from the list below and follow the links to find free routes and turn-by-turn directions from the Ride with GPS platform, curated by local volunteers.
scenic road ride

Driftless Region’s Most Scenic Ride – 82 miles /3,864 ft 

This challenging ride has fantastic views and four big climbs, making it a perennial favorite that we sometimes just call the DRMSR. It’s is designed so that by the end of the day, you will have spent an equal amount of time on the bluff tops and in the valleys. The challenging climb up local legend Tschumper Road rewards you with quiet and narrow country roads.

West Salem Dairy Days Classique – 66 miles / 3,107 ft

Originally known as Le Coulee Classique, this version of that older route is a moderately hard ride with four medium climbs. The many farms along the way mean you will see lots of herds, and the ride gets its name from the yearly celebration of dairy farming held in West Salem. You return through the scenic Mindoro cut, a popular route for motorcyclists and bicyclists alike.

A pace line of riders with a barn and silo in the background
View of the city of La Crosse from Grandad Bluff

This is a short loop with one easy and one hard climb. It’s a favorite for locals who need a quick after-work training ride. Since it’s so short there’s no convenience store stops on this self-supported route, but since it’s La Crosse there are frequent drive-ins and roadside taverns along the way.

Whitehall English Century-100 miles / 3,574 ft 

With only seven medium-size hills over 100 miles, this is considered a moderate ride in our region. Quiet county roads along most of the route offer plenty of opportunities to ride two-up, enjoying the company of other cyclists and the gorgeously green scenery in the farm and bottomlands.

paved road winding through green countryside
Three roadies on paved road with a barn in the background

Apple Blossom Loop-35 miles / 1,240 ft

This is a very popular loop, often tackled after work by local riders. It’s also a good place to start for anyone new to road biking, or to the Driftless region. It heads west across the mighty Mississippi and through the village of La Crescent before beginning a journey up the rural Pine Creek Valley.