Top 5 road trips in Wisconsin

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

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. And while there’s plenty to do within Wisconsin, its central location in the heart of the Midwest means it’s also a great place to start (or end) a road trip that visits other must-see states like Minnesota, Michigan, Illinois and Indiana.

Get active kayaking Lake Superior on your road trip around Wisconsin © Hoogz Photography / Shutterstock

The ultimate Wisconsin road trip

Best road trip to sample a bit of what Wisconsin has to offer

Milwaukee-Bayfield; 441 miles (710km)

Start out in Wisconsin’s largest city, where you can hang out at Milwaukee’s best beaches or indulge in “big city” entertainment and nightlife before making your way to the tiny towns in the northern part of the state. And while you could easily do the drive in a day, you’ll want to allow about a week so you can explore the unique food and bike culture in Madison, go for a riverboat tour in Wisconsin Dells, and visit a winery in Eau Claire before reaching the southern shore of Lake Superior.

When you arrive in Bayfield, hiking is a great option year-round but if you visit in the summer, be sure to kayak to the lakeshore’s famous sea caves. Come winter, if the ice freezes over sufficiently, you can even hike over Lake Superior to reach the caves.

Sample Wisconsin’s famous beer and cheese

Best road trip for food and drink enthusiasts

Kenosha-Madison; 115 miles (185km)

Wisconsin is known for two things: good beer and great cheese. And while you can find both pretty much anywhere in the state, you’ll find the most options along this route, which could be modified as a long day trip or stretched out to a weekend road trip. Start out in Kenosha and visit the gigantic Mars Cheese Castle (conveniently located right on the highway) and the Kenosha Brewing Company, which is located at the site of the first post-Prohibition brew pub in the Midwest.

Make your way to Milwaukee, where the West Allis Cheese and Sausage Shoppe and Wisconsin Cheese Mart are your go-to spots for divine dairy. Beer lovers have a seemingly endless number of breweries to visit, including Lakefront Brewery, Miller Brewing, MobCraft, Milwaukee Brewing Company, and Pabst Brewery – all of which offer brewery tours. When you arrive in Madison, enter cheese heaven at downtown’s Fromagination then have your pick of breweries: LGBTQIA+- and female-owned Giant Jones Brewing Company, gluten-free ALT Brew, and the appropriately named Capital Brewery, which is one of the oldest craft breweries in the country.


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A road with colorful trees in fall in Door County, Wisconsin, USA
There are tree-lined roads aplenty to admire the fall colors on a road trip through Wisconsin © Shutterstock

Fall in love with fall foliage

Best road trip for leaf peeping

Wisconsin Dells-Bayfield; 294 miles (473km)

Wisconsin is jam packed with state parks and forests so you’ll find fabulous fall foliage all over the state but if you don’t have time to explore every corner of the state, this is the route for you.

Start off in the waterpark capital of the country, Wisconsin Dells, where leaf peeping is best enjoyed in nearby Mirror Lake State Park and Devil’s Lake State Park. For a different vantage point, take an Upper Dells riverboat tour, where brilliant fall colors can be enjoyed alongside the region’s iconic sandstone formations.

Drive north through the stunning Chequamegon-Nicolet National Forest and along tree-lined country roads that will bring you to the waterfront town of Bayfield. While tremendous leaf peeping is available just by driving around the area, it’s worth planning some hikes in and around the Apostle Islands National Lakeshore. If you have a few more days, also consider driving up to the Door County peninsula, in the “Wisconsin’s thumb” region.

The Quintessential Midwestern road trip

Best road trip to experience the Midwest at its finest

Milwaukee-Detroit; 566 miles (911km)

Not only is the great state of Wisconsin sufficiently diverse and delightful in its own right, it’s also conveniently located smack dab in the middle of the Midwest, making Milwaukee to Detroit one of the best road trips that start in Wisconsin. If you’re making your way from the west, you could also start in another rockstar Midwestern city, Minneapolis. If beginning in Wisconsin, start off with these 10 things to do in Milwaukee; visit Chicago’s beloved “Bean” sculpture in Millennium Park; and explore the Kurt Vonnegut Museum in Indianapolis before arriving in the country’s former capital of cars, Detroit. Technically, the drive could be completed in about nine hours but you’ll want to allow at least a few days in each destination to get to know it a bit.

You could also start this trip in Minneapolis if you have a few extra days and get to know another great Midwestern city.

Couples at Warrens Cranberry festival enjoying their time getting photos taken while playing in a pool of cranberries, USA
Time your trip for the harvest to join in the fun at Warrens Cranberry Festival © Aaron of LA Photography / Shutterstock

The Cranberry Highway road trip

Best road trip for experiencing Wisconsin cranberry culture

Wisconsin Rapids-Warrens; 47 miles (76km)

Welcome to the cranberry capital of the world, Central Wisconsin. This part of the state claims nearly 60% of the entire country’s cranberry production and harvest season is typically September and October, making early fall the best time to visit.

Explore Wisconsin’s Great River Road

Best motorcycle road trip

Prescott-Kieler; 250 miles (402km)

Harley Davidson is from Milwaukee so motorcycle culture runs deep throughout the entire state. Some of the best motorcycle excursions in Wisconsin can be found around the state’s Driftless Area, where rustic roadways intersect with grand waterways like the mighty Mississippi River. The Driftless Area is known for a mixture of dense forests, restored prairies and countless lakes and wetlands (which can be great for wildlife watching).

This particular route is special because it takes you along the state’s only National Scenic Byway. The 250-mile Wisconsin Great River Road links the people, resources and history of 33 small river towns, with plenty of places to overnight and have a look around. Note that Google Maps will automatically route you along a more direct, inland path from Prescott to Kieler but for the best scenery, just follow the Mississippi River.

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