The Best Road Trips In Wisconsin

Road tripping is a great American tradition and a great way to have new experiences and see some new sights without needing to hop on a plane. From the comfort of a car, you can view stunning vistas, charming towns and, best of all, eat food on the go while enjoying the fresh air and changing scenery. Here are our favorite drives to take in the state of Wisconsin.

Did you know – Culture Trip now does bookable, small-group trips? Pick from authentic, immersive Epic Trips, compact and action-packed Mini Trips and sparkling, expansive Sailing Trips.

Great River Road National Scenic Byway

Known more prosaically as Highway 35, this road trip is a 250mi (402km) drive along the Mississippi River. If you’re paying attention on the way, you might even be able to spell Mississippi by the end of the trip. Stretching from Prescott to Potosi, this drive has 33 charmingly small and quaint towns to visit along the way, many with art galleries, wineries and historic sites of interest to draw your attention. Pull up your best road trip playlist and get going.

A road trip with possibly the best name ever, Cranberry Highway is the trip that fruit lovers or Thanksgiving lovers should choose, as it winds its way through century-old cranberry bogs for almost 50mi (80km). You can see the red berries from the highway – a beautiful sight. The route runs from Wisconsin Rapids to Warrens and then between Pittsville and Nekoosa. If you’re keen to see more cranberries, you can explore Highway 54, Highway 173, Highway 13 and then county roads in Wood, Juneau and Monroe County.

Lake Superior Byway

This road trip is a Wisconsin classic, and it runs alongside Lake Superior for a route blessed with natural beauty. At 70mi (113km) long, you could do it in one day or split the trip by spending the night at one of the many harbor towns and historic fishing villages you pass. You’ll enjoy views of lush forests, sparkling sandy beaches and the clear blue water of Lake Superior; you should definitely pack your bathing suit because you won’t be able to resist taking a dip.

Highway 42

At the northernmost tip of the peninsula, past Gills Rock, lies Wisconsin’s world-famous curvy road. Resembling a child’s drawing of a winding, bumpy road, it wends its way through stunningly bright and vivid fall foliage. This is one of the most photographed parts of the whole state, and although the most beautiful portion is only 15mi (24km) long, it is an iconic road to take. We recommend visiting midweek or at the beginning or end of each autumn season, as it can get very busy.

Elkhart Lake

As long as you’re driving along it, it counts as a road trip, right? Elkhart Lake, found around 80 minutes north of Milwaukee, is rightly famous for its watersports – but the Road America racecourse nearby is a world-favorite. Drawing visitors who love amateur racing since 1955, it is worth a trip here to catch a race on this 4mi (6.4km) track. While you’re there, the nearby Kettle Moraine State Forest has many miles of trails for running and biking.

Highway 33 Scenic Drive

This road trip is one of the state of Wisconin’s coast-to-coast routes – not from the east coast of America to the west, but from Lake Michigan to the Mississippi River. Highway 33 has the honor of being one of the few state highways to have a hairpin turn, so buckle up. The route takes you through Wildcat Mountain State Park, which has beautiful scenic viewing places as well as some spectacular hiking. You can also stop to go canoeing in Wonewoc, which is worth seeing. Summer and fall are the best times to travel here.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.