Before heading out on your road trip through Driftless Wisconsin be sure to visit 511 Wisconsin for any potential delays, detours, and road closures.

motorcycle couple

Photo by Steve Mason

The Driftless Region in Wisconsin has a variety of scenic highways and byways winding along rivers and through charming midwest communities. These roadways are perfect for a scenic trip with friendly towns, restaurants, bars, and places to stay to hit along the way. A motorcycle trip through the Driftless Region will also reveal the unique beauty of the area. So grab your helmet and follow us on a one day trip through the Driftless Region by motorcycle.



Start your ride in La Crosse, WI, a bustling city on the Mississippi River with a historic downtown district. There are places to fill up your tank with gas and enjoy a morning view of the Mississippi River. From there you can head to Stoddard where you can hop on Highway 162 and head south through Chaseburg, then to Highway 14 near Coon Valley and enjoy a sunny morning ride to Westby, WI.

While you’re in Westby, grab a hearty breakfast and some coffee at Borgen’s Cafe before heading downtown to explore the shops, take in the Norwegian heritage, and stop for a photo op with Ole, the city’s wood-carved mascot.

From there it is just a short, but scenic drive to Hillsboro. You can travel along Highway 27 through Cashton and then Highway 33 through Ontario to see beautiful timber covered hills, lush green valleys, numerous trout streams, limestone cliffs, and scenic farmland. These routes also pass through the largest Amish community in Wisconsin, Wildcat Mountain State Park, and nearby Kickapoo Valley Reserve. You can stop in Cashton and Ontario to explore the history of the areas and admire the beautiful outdoor spaces.

Wildcat Mountain

Wildcat Mountain State Park


Once you arrive in Hillsboro, there are a variety of things you can do. If you’ve already worked up an appetite since breakfast, the Hillsboro Brewing Company is an excellent choice for an early lunch. Though it wouldn’t hurt to stop and explore the brewery even if you don’t plan on eating, as it is located in a gorgeous newly restored turn-of-the-century building and has a nice gift shop.

If you are from out of town and plan on staying in the Driftless Region, or you want to turn a day ride into a 2 day trip, the Blue Highway Lodge is a great choice for an overnight stay that is popular with motorcycle enthusiasts. Since this day route is a loop, you can even adjust your starting point to Hillsboro, so you end up back in town at the end of the day.

After lunch, head southeast to Viroqua, a great small town in Vernon County filled with history, entertainment, eateries, and charming local shopping. The downtown district has been named on the Wisconsin and National Register of Historic Places and the area features fun stops like the Viroqua Food Co+op, Vernon Vineyards, and Wonderstate Cafe.

red corvette

Photo by Strelciuc Dumitru


As the afternoon fades into evening, you’ll saddle back up and head towards Prairie du Chien on Highway 27, the second-oldest settlement in the state of Wisconsin. As the sun begins to set for the evening, you will start a very scenic leg of the drive on the Wisconsin Great River Road. The drive winds along the Mississippi River and offers beautiful views of the river and the unique limestone bluffs of the Driftless.

If you just want to stop for an early dinner before heading home, Prairie du Chien has great options like the Jones Black Angus Supper Club and The Barn Restaurant. But the Great River Road will also take you through the river communities of Lynxville, Ferryville, Desoto, and Genoa as you make your way back up to La Crosse. Enjoy the ride along Wisconsin’s only All American Road, and it’s a National Scenic Byway as well. If you time it right, you can catch a stunning view of the sunset over the Mississippi.

You can end your day at one of the many lodging establishments along your tour, and enjoy an evening meal nearby.

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Driftless WisconsinThere is simply no better place to explore, by car, by bike, or by boat. The scenery when you explore the Driftless Wisconsin Area is unmatched. The history is fascinating. The people and communities are diverse. Around every bend of the road, every twist of the river, something interesting awaits.

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