Driftless Region: Wisconsin Weekend Getaways for Riders

Touring Driftless Wisconsin on Two-Wheels!

The Driftless Area is one of the best Wisconsin weekend getaways, spanning several counties and nearly 30 communities east of the Mississippi River. It’s a natural wonderland of unglaciated majesty to behold. First settled by Amish families – many of whom remain – there is a feeling of quiet, peaceful living here.

This is the very reason so many visitors are drawn to our scenic bluffs, winding roads, and trickling streams year after year. The driftless area offers a break from the busyness of everyday life; a chance to get away – even just for a weekend.

We’re Wisconsin’s Outdoor Recreation Destination, here in Boscobel, famous for our open-air adventures. Weekenders often enjoy hunting, fishing, hiking, camping, canoeing/kayaking, and (especially) cycling, mountain biking, and motorcycle riding.

Wisconsin Weekend Getaways: From Madison to Boscobel

Welcome to the driftless area, Madison natives! Whether you’ll be arriving on two wheels or four and a bike rack, there are many road trip memories waiting to be made. The most direct route from Madison to Boscobel is to head northwest on Highway 14.

First Stop – The Shoebox

Before long, you’ll come across the town of Black Earth, home to a recognizable roadside attraction: The Shoebox – aka the largest shoe store in the Midwest!

Here you’ll find quality shoe brands of all sorts of styles. Even if you’re not a serious buyer, it’s worth a stop to browse and interact with the friendly and helpful staff. And, at the very least, you can snap a great photo next to the hat-wearing cow statue on their front lawn.

Second Stop – Spring Green, WI

Hopping back on the road, the flat farmland around you will soon begin its transition to Driftless Wisconsin hill country. Once you cross the Wisconsin River, you’ll run smack dab into Spring Green.

This driftless hotspot was made famous by American architects, Frank Lloyd Wright and Alex Jordan, Jr., and their building designs: Taliesin and House on the Rock. Both are must-see attractions, if you have a day to spare.

Taliesin is an 800-acre property that served as home, school, and studio to Frank Lloyd Wright during the twilight of his illustrious career. Today, its commanding structure and surrounding gardens are considered “the most complete embodiment of Wright’s philosophy of organic architecture” by many.

Inspired by Wright’s work, the House on the Rock was designed by one of his former pupils, Alex Jordan. Although, as legend has it, Jordan constructed his masterpiece in response to Wright’s dismissal of his work.

The awe-inspiring buildings and resort are filled to the brim with interactive entertainment – from animated musical displays, such as the world’s largest carousel, to the Heritage of the Sea exhibit featuring a life-sized whale sculpture! Be sure to bring comfortable shoes (see…you’re glad to stopped at the Shoebox now) because there’s a bunch of ground to cover.

Cruise the Scenery into Boscobel!

When it’s time to hit the ol’ dusty trail again, cruise westward on Highway 14 and turn left onto scenic Highway 60 in Gotham (sorry no Batman here). You can now simply enjoy a beautiful ride along the Lower Wisconsin Riverway complete with rocky outcroppings and historic farms, churches, and schoolhouses.

They may have been around a long time, but trust us…they never get old. Continue on this route all the way to Highway 61, which takes you right into Boscobel to enjoy all sorts of awesome outdoor activities.

Now that you’ve arrived, you and someone special should pop a cork! Be sure to visit Spurgeon Vineyards and Winery. Just a 30-minute ride from Boscobel’s downtown, Travel Wisconsin recently listed this family-run getaway spot as one of the best local wineries in the state.

And, of course, there’s nothing wrong with heading back the way you came after a fruitful trip! It’s only a half day’s ride from Boscobel to Madison by bicycle.

Wisconsin Weekend Getaways: From Dubuque to Boscobel

Wisconsin Weekend Getaways: From Dubuque to Boscobel

Will you be joining us from the south? Excellent – there’s still plenty of Driftless Wisconsin to explore on the way up and down Highway 61. Let’s start with one of Wisconsin’s most obvious draws: our beer.

First Stop – Potosi Brewery

Just off the beaten path of what is known as the Great River Road sits Potosi Brewery in the small-town of (you guessed it) Potosi, Wisconsin. This historic brewery literally pre-dates the American Civil War and is known for its use of fine ingredients for small-batch craft beer.

The facility is not just a brewpub and restaurant. The National Brewery Museum, beer garden, gift shop, and Great River Road Interpretive Center are also on-site, providing context to the oft-overlooked aspects of Wisconsin brewing. Potosi is truly a one-of-a-kind river town to hang out in, so cheers to the weekend!

Second Stop – Fennimore Railroad Museum

But let’s get back on track. If you continue north on Highway 61, you’ll eventually find yourself in Fennimore. We hope you have a playlist featuring “Locomotion,” because it’s time to tour the Fennimore Railroad Museum.

This free experience offers a glimpse of Midwest narrow-gauge train history and the important economic role the rails played in the lives of both city and country folk. Proudly resting out front is a restored 1907 Davenport 2-6-0 locomotive nicknamed “Dinky” for its small, three-foot-gauge.

Inside the museum you’ll come across working miniatures simulating the exact track routes followed by early conductors along with railroad artifacts to help tell the story. And they aren’t just blowing smoke.

You’ve Arrived in Boscobel, WI!

After getting back on 61, you’ll soon complete your quest to reach Boscobel. Now that you’ve arrived, there are tons of outdoor adventures to embark on and great places to stay in our area. Boscobel’s central location along the Lower Wisconsin Riverway positions us within reach of campgrounds, cabin rentals, or quiet, comfortable stays.

Bonus tip: If you can swing it on your way home, we have an additional recommendation. There’s no better way to follow up a few days of scenic rides, fly fishing, and/or canoeing/kayaking than a night or two at Walnut Ridge rental cabins.


Nestled far from city life, Walnut Ridge provides the rustic serenity of remote cabin living with all the comforts of a luxury resort. Light a magical fireplace, soak in a jacuzzi tub, and let your cares melt away in the complete tranquility of the area.


You simply can’t end one of your Wisconsin weekend getaways on a better note. It’s not possible.

Touring Driftless Wisconsin on a Bicycle or Motorcycle

Whether you’re coming from Madison, Dubuque, or some other place, we invite you to discover the joys of our Wisconsin weekend getaways through twisting, rising, and falling landscapes along highways 60 and 133.

These routes mirror the banks of the Wisconsin River and are utilized by riders to immerse themselves in the driftless landscape. Pairing our wealth of recreational activities with a unique selection of nearby attractions creates a wonderful road trip experience for cyclists and bikers.

We know the phrase is, technically, “it’s not about the destination; it’s about the journey,” but in Boscobel, we say: “Why shouldn’t you have a great time for both?”

Start planning one these Wisconsin weekend getaways to the Driftless area today, and connect with us on Facebook, Instagram, or Pinterest to keep up with insider tips on how to best enjoy our neck of the woods!