The Best Road Trips in Wisconsin

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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.

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.

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.

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.

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.