Before heading out on your road trip through Driftless Wisconsin be sure to visit 511 Wisconsin for any potential delays, detours, and road closures.
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. Plus, as a part of Driftless Wisconsin’s summer of 2023 Special Deals, you can take advantage of great savings at area businesses when you visit between August 1st and September 30th, 2023. So grab your helmet and follow us on a one day trip through the Driftless Region by motorcycle, and save money with some great deals along the way.
Morning
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. A great place to get a souvenir is at Dregne’s Scandinavian Gifts, where shoppers can receive 15% off of a purchase of $20.00 or more as a part of Driftless Wisconsin’s summer of 2023 “Special Deals.” Be sure to also stop into the Westby Co-op Creamery to pore over the selection of local cheeses, yogurt, and butter. You can buy any Westby Creamery branded item and get an item of equal or lesser value for free between August 1st and September 30th, 2023.
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. If you do a little shopping in Cashton, you can enjoy half off a 2nd Juusto Baked Cheese when you buy one Juusto Baked Cheese at Pasture Pride Cheese. While in Cashton, visitors can also stop into Down a Country Road and receive a free map ($5 value) of Amish country businesses by mentioning the Driftless Wisconsin Special Deals and making a purchase at the shop.
Afternoon
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. By asking the staff for their Drifltess Wisconsin “Special Deal,” you can buy one pint and get one pint free of equal or lesser value from August 1st to September 30th.
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. Another accommodation in the area with “Special Deals” includes the Driftwood Inn Motel in Ontario ($100 per night for the apartment at the motel (regular price is $140) with a 2 night minimum).
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 (where you can get a free glass of wine by mentioning Driftless Wisconsin “Special Deals”), and Wonderstate Cafe. If you or someone you know is an avid fisherman, be sure to stop into Driftless Angler while you’re in Viroqua to get 20% off all apparel, tools, and packs between August 1st and September 30th.
Photo by Strelciuc Dumitru
Evening
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.
Prairie du Chien is also a great location to take advantage of great savings on your trip. If you end up in Prairie du Chien at the end of your ride, stay at the Quality Inn & Suites and book a queen suite or king suite for $149.99 as a part of Driftless Wisconsin’s “Special Deals.” The deal includes an Eagles Landing wine, Sweet Tooth chocolate, towel swans, roses and 2 Huckleberry’s Restaurant coupons for $2 off of meal per person at check-in. Other participating Prairie du Chien businesses with valid deals include The Planted Tree Gallery, Prairie Fun Land, The Funky Zebras, Angel411, and The Broken Ladder.
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 (receive 20% off any menu item, not including gratuity by mentioning “Special Deals”). 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.
There 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.