Unforgettable Road Trips in Wisconsin

Wisconsin was made for road trips. Whether you’re looking for a traditional Wisconsin experience centered around visiting the best craft breweries and farm-fresh cheese stands or you want to spend time hiking, biking, and wildlife watching, the Badger State won’t disappoint.

Why Wisconsin is Perfect for Road Trips

The roads here are generally well-paved and well-marked. Should you get lost, just pull into a gas station or bait and tackle shop, and a friendly face will happily help you get re-oriented. Moreover, while there’s plenty to do within Wisconsin itself, its central location in the heart of the Midwest makes it an excellent starting point for road trips to neighboring states like Minnesota, Michigan, Illinois, and Indiana.

The Ultimate Wisconsin Road Trip

Best route to sample Wisconsin’s offerings

Milwaukee to Bayfield; 441 miles (710 km)

Begin in Wisconsin’s largest city, Milwaukee, where you can enjoy stunning beaches and indulge in a vibrant entertainment scene before heading north to explore the charming small towns of the state. Although the drive can be completed in a single day, it’s recommended to take your time—spending about a week exploring the unique food and biking culture in Madison, enjoying a riverboat tour in Wisconsin Dells, and visiting local wineries in Eau Claire before reaching the southern shore of Lake Superior.

Upon arriving in Bayfield, hiking opportunities abound year-round; however, if you visit in the summer, don’t miss kayaking to the lakeshore’s famous sea caves. In winter, if the ice permits, you can hike over Lake Superior to reach these stunning formations.

Sampling Wisconsin’s Famous Beer and Cheese

Ideal road trip for food and drink enthusiasts

Kenosha to Madison; 115 miles (185 km)

Wisconsin is renowned for its exceptional beer and artisanal cheese. While you can find both throughout the state, this route provides numerous options, making it perfect for a day trip or a weekend excursion. Start in Kenosha and visit the iconic Mars Cheese Castle, located conveniently along the highway, and the Kenosha Brewing Company, situated at the historic first post-Prohibition brew pub in the Midwest.

Proceed to Milwaukee, where the West Allis Cheese and Sausage Shoppe and Wisconsin Cheese Mart are must-visit spots for dairy enthusiasts. Beer lovers will find a plethora of breweries, including Lakefront Brewery, Miller Brewing, MobCraft, Milwaukee Brewing Company, and Pabst Brewery, all offering fascinating brewery tours. In Madison, experience cheese bliss at Fromagination and select from many breweries, including the female-owned Giant Jones Brewing Company and the historic Capital Brewery, one of the oldest craft breweries in the country.

Enjoying the Fall Foliage

Best road trip for leaf peeping

Wisconsin Dells to Bayfield; 294 miles (473 km)

Wisconsin boasts an abundance of state parks and forests, offering fabulous fall foliage across the landscape. Starting in Wisconsin Dells, renowned for its water parks, the best leaf peeping can be enjoyed at nearby Mirror Lake State Park and Devil’s Lake State Park. For a unique experience, consider taking a riverboat tour along the Upper Dells, where breathtaking autumn colors complement the region’s iconic sandstone formations.

Drive north through the stunning Chequamegon-Nicolet National Forest, along picturesque country roads leading to the waterfront town of Bayfield. Though phenomenal views are possible simply by cruising around the area, consider planning hikes in and around the Apostle Islands National Lakeshore. If time allows, take a trip up to the Door County peninsula, referred to as “Wisconsin’s thumb.”

The Quintessential Midwestern Road Trip

Best road trip to experience the Midwest

Milwaukee to Detroit; 566 miles (911 km)

Wisconsin is not only diverse and delightful in its own right, but it also serves as a convenient gateway to other parts of the Midwest. The journey from Milwaukee to Detroit is one of the top road trips starting in Wisconsin, with possibilities for itineraries including Chicago’s famous “Bean” sculpture in Millennium Park and the Kurt Vonnegut Museum in Indianapolis before arriving in Detroit, the nation’s historical automobile capital. While the drive may be completed in about nine hours, allocating a few days at each destination will enhance your exploration experience.

The Cranberry Highway Road Trip

Best road trip for experiencing cranberry culture

Wisconsin Rapids to Warrens; 47 miles (76 km)

Welcome to the cranberry capital of the world, Central Wisconsin, responsible for nearly 60% of the country’s cranberry production. The harvest season spans September and October, making early fall the prime time for a visit. The region features an official 50-mile Cranberry Highway, with the most attractions situated in the two cities of Warrens and Wisconsin Rapids. Explore the Wisconsin Cranberry Discovery Center in Warrens, snap a photo at Historic Marker 86 in Cranmoor, and learn about the fruit’s history at the South Wood County Historical Museum in Wisconsin Rapids. Don’t miss a tour at the century-old Rooted in Red cranberry farm, where you can even immerse yourself in the bog.

Explore Wisconsin’s Great River Road

Best motorcycle road trip

Prescott to Kieler; 250 miles (402 km)

With Harley Davidson originating in Milwaukee, motorcycle culture runs deep throughout Wisconsin. One of the best motorcycle excursions can be found in the state’s picturesque Driftless Area, where scenic roadways intertwine with the majestic Mississippi River. This route is special, as it encompasses the state’s only National Scenic Byway. The 250-mile Wisconsin Great River Road connects 33 small river towns filled with history and plenty of stopping points for overnight stays.

When planning your route, note that while Google Maps may suggest a direct route, for the best scenery, opt to follow the Mississippi River instead.