15 Fun Must-Do Wisconsin Road Trips

Best Road Trips in Wisconsin

A road trip around Wisconsin is something you’ll remember forever.

To make sure you get the most from your road trip, plan ahead to prevent any hiccups along the way.

Check for any planned roadworks, weather conditions, etc.

This guide should give you some ideas to get started. I’ve included the distances of the trips.

This will give you some idea of how long each will take – however, this is entirely dependent on how many stops you make along the way.

If you believe that journey is as important as the destination, read on for some of the best Wisconsin road trips.

Buy here the perfect Wisconsin road trip itinerary

1. The Big Cities of Wisconsin

Start in: Kenosha

End in: Green Bay

Distance: 250 miles

If you’re a city lover then this is the road trip for you.

Starting in Kenosha and terminating in Green Bay, by way of Milwaukee and Madison, this is a journey in which you’ll certainly want to enjoy a few stops along the way.

In fact, you’ll probably want to stay (at least for a night) in all of these cities.

Explore all the amazing things to do in Madison and the fun and unique things to do in Milwaukee!

There’s so much to explore in all of these cities that they’re all destinations in their own right.

However, as this article is about being out on the road then let’s focus on the end point of Green Bay, a vibrant city with bags of fun activities.

Home to the famous Green Bay Packers, this friendly city also features many other attractions to make your stay a joy.

Make sure to enjoy all the fun things to do in Green Bay while you’re here!

There are lots of great hotels and resorts in Green Bay to stay at before heading back home.

Book here the best tours in Green Bay, WI

2. The Door County Coastal Byway

Start in: Northport

End in: Sturgeon Bay

Distance: 66 miles

This road trip is perfect for those wishing to see the famous fall colors in Wisconsin.

Fall in Wisconsin is a truly magical time and this Door County road trip is a perfect way in which to experience it.

Beginning in Northport, this incredibly scenic route will skirt the sensational coast of Door County, providing you with jaw-dropping views at every turn.

At 66 miles, it’s not a long journey but you’ll want plenty of stops along the way to take in the stunning scenery (and get lots (and lots!) of photos.

Your journey will end in the idyllic fisherman’s mecca of Sturgeon Bay.

The town has a very laid-back, relaxing vibe, and great kayaking, canoeing, sailboat rides, and jet-skiing.

This road trip is certainly one of the most relaxing things to do in Door County.

Book here the best vacation rentals in Door County

3. The Great River Road National Scenic Byway

Start in: Prescott

End in: Potosi

Distance: 250 miles

The Great River Road National Scenic Byway is one of the iconic Wisconsin road trips.

Otherwise known as Highway 35, this trip takes you through numerous enchanting small towns such as Stockholm, Alma, and Trempealeau.

As you flank the mighty Mississippi River, there are spectacular views along the way, and this really is a truly amazing scenic drive.

The Great River Road actually extends through ten other states and goes on for 3,000 miles.

However, the 250-mile Wisconsin is perfect to cover in a weekend.

The show ends in the ‘Catfish Capital of Wisconsin’, Potosi.

In addition to fishing, Pelosi is a laid-back town with a rich brewing tradition.

Make sure to check out the Potosi Brewery and National Brewery Museum.

There’s also great camping, birdwatching, and tubing on the river to be had here. Have fun!

Buy here the perfect Wisconsin road trip itinerary

4. Milwaukee to Wisconsin Dells

Start in: Milwaukee

End in: Wisconsin Dells

Distance: 124 miles

If you’re looking for scenic drives near Milwaukee then this road trip fits the bill.

There are lots of scenic locations en route and great places to take a break, including the city of Madison which is roughly at the halfway point of the journey.

This is also one of the best getaways for spring break in Wisconsin due to Wisconsin Dells’ reputation as a fun town.

So if you’re planning spring break road trips from Wisconsin, this is one of the best choices for you.

Although there are many fun things to do in Wisconsin Dells year round!

Due to the relatively short journey time, this is also an option for those seeking day trips from Milwaukee.

The trip winds up in the waterpark capital of the world, Wisconsin Dells, a city where the emphasis is on fun, and then some more fun.

All-round, this is one of the best road trips from Milwaukee.

Book here the best tours in Wisconsin Dells

5. The Kettle Moraine Scenic Route

Start in: Elkhart Lake

End in: Whitewater Lake

Distance: 115 miles

This beautiful route takes you through one of the best state parks in Wisconsin.

The route traverses six counties and the sensational natural landscapes make it undoubtedly among the best family road trips from Wisconsin.

You’ll go through forests, alongside lakes, and plenty of charming towns and villages along the way.

Another plus is that it’s also relatively easy to access the trail from most of the major cities in the state.

If you like to stay active on your trip, then stay a while in the stunning Kettle Moraine State Forest, as it’s home to some of the very best outdoor activities in Wisconsin.

For example, the Scuppernong Trail System in Southern Kettle Moraine is home not only to some of the best hiking trails in Wisconsin, but also many of the finest mountain bike trails you can find.

Buy here the perfect Wisconsin road trip itinerary

6. The Cranberry Highway

Start in: Wisconsin Rapids

End in: Warrens

Distance: 50 miles

One of the most iconic Wisconsin road trips is the Cranberry Highway.

The reason this fifty-mile stretch of road is titled such is that it takes you through fields full of the state’s famed crop for almost the entire duration.

Along the way, make sure to take in Glacial Lake Cranberries, a cranberry farm that has been in operation since way back in 1873.

From there, your next stop should be Pittsville, where you can take the fascinating Splash of Red Cranberry Tours for a close look at all things cranberry farming.

The journey terminates in Warrens, the self-styled Cranberry Capital of Wisconsin.

If you’re there during September, don’t miss the Warrens Cranberry Festival, where 120,000 people descend on the town for cranberry-based fun!

It’s one of the best fall festivals in Wisconsin, so you don’t wanna miss it!

Book here the best cabin rentals in Northern Wisconsin

7. Coast to coast on Highway 33

Start in: La Crosse

End in: Port Washington

Distance: 93 miles

Driving from coast to coast along Highway 33 is one of the best Wisconsin road trips to complete in a day.

Traveling west to east, there are some great locations to take in.

While there are numerous small towns in which you could take a break from driving, make sure to stop in the fantastic town of Portage.

In Portage there are rivers that link the Great Lakes all the way to the Gulf of Mexico!

If you like to hike, you can walk part of the National Ice Age Trail here.

The journey ends right on the edge of the border with Minnesota, in the vibrant town of La Crosse, where you can witness the world’s largest six-pack!

This huge landmark is made from brewery tanks decorated to resemble a six-pack of beer.

Buy here the perfect Wisconsin road trip itinerary

8. Highway 42 from Manitowoc to Algoma

Start in: Manitowoc

End in: Algoma

Distance: 15 miles

The very short trip will take you from Manitowoc to Algoma, encountering museums, beaches, and sensational views along the way.

You will no doubt have seen photographs of this famous stretch of road somewhere (it’s the famous ‘curvy road’ that winds through beautiful woodland).

In addition to the fun, windy road, you’ll also encounter some of the storied lighthouses of Wisconsin as you wind your way along the route.

The route goes through Two Rivers (the birthplace of the ice cream sundae!) and Kewaunee before ending up in the relaxing town of Algoma.

In Algoma you can see the Algoma Pierhead Lighthouse, making this a great Wisconsin lighthouse road trip.

Buy here the perfect Wisconsin road trip itinerary

9. The Waterfalls of Wisconsin

Start in: Big Manitou Falls

End in: Copper Falls

Distance: 120 miles

If you’re seeking inspiration for Wisconsin road trip ideas, then how about visiting some of the best waterfalls in Northern Wisconsin?

Wisconsin is packed with sensationally beautiful waterfalls and this trip will let you see four of the finest.

Beginning in Big Manitou Falls and ending in Copper Falls, by way of Lost Creek Falls and Morgan Falls, this is one the most stunning of Wisconsin scenic drives.

The real highlights come at the beginning and the end, with Big Manitou Falls being the highest waterfall in Wisconsin.

Copper Falls sit within Copper Falls State Park, one of the most beautiful state parks in Wisconsin.

If you’d like to stay, go camping at Copper Falls State Park Campgrounds, one of the most fun things to do in Northern Wisconsin!

Book here the best cabin rentals in Northern Wisconsin

10. The Frank Lloyd Wright Trail

Start in: Richland Center

End in: Racine

Distance: 200 miles

If you’re interested in the famous American architect, Frank Lloyd, then this is one of the most interesting and educational Wisconsin road trips that you could take.

Starting in Richland Center, the 200-mile route will take you through Spring Green, Madison, and Milwaukee, before reaching the endpoint in Racine. 

There’s so much to see and do along the route that you’ll want to break the journey up and take a few overnight stops along the way.

Each of the cities features iconic Frank Lloyd Wright-designed buildings that must be seen.

At the journey’s end in Racine, you can see Wingspread and the SC Johnson Administration Building and Research Tower, two famous Wright landmarks.

Buy here the perfect Wisconsin road trip itinerary

11. The Lake Superior Byway

Start in: Barksdale

End in: Bayfield

Distance: 70 miles

This Wisconsin road trip takes you along the shores of Lake Superior, without doubt one of the best lakes in Wisconsin.

This 70-mile stretch is truly sensational, going along the Apostle Islands National Lakeshore, one of the most geographically stunning locations you’re ever likely to see.

The crystal-clear waters of Lake Superior form a dramatic backdrop to the forests, beaches, harbor towns, orchards, fishing villages, and farms you’ll come across along the way.

The journey terminates in the beautiful city of Bayfield (the smallest city in Wisconsin), where you’ll definitely want to spend some time.

In Bayfield, you’ll find a friendly town with a laid-back, relaxing vibe and great dining options.

The ferry to Madeline Island also departs from here, making it a great stop-off point en route to the Apostle Islands.

Book here the best cabin rentals in Northern Wisconsin

12. The Lower Wisconsin River Road

Start in: Lodi

End in: Prairie du Chien

Distance: 100 miles

Starting in Lodi and ending in Prairie du Chien, this lesser-traveled road trip takes you all the way from the Empire Prairie to the iconic Mississippi River.

This is one of the best Wisconsin road trips for those who like to be by the riverside.

The route takes you along the banks of the Lower Wisconsin River as it winds and weaves its way along the 100-mile route.

Known as the ‘River of a Thousand Isles’, the Lower Wisconsin River is a fascination all in its own right.

The river has constantly shifting sandbars, channels, and flows that vary depending on the weather conditions.

You’ll finish the trip in the charming town of Prairie du Chien, the oldest European settlement on the Upper Mississippi River.

Buy here the perfect Wisconsin road trip itinerary

Best Road Trips from Wisconsin to Nearby States

13. Milwaukee to Detroit

Start in: Milwaukee

End in: Detroit

Distance: 566 miles

This is one of the best road trips starting in Wisconsin for music lovers, taking in cities with rich musical histories, such as Chicago, Ann Arbor (home of the legendary Iggy Pop), and ending up in Detroit.

A quintessential Midwest road trip, this is one of the road trips from Wisconsin that is best done in stages, as you’ll undoubtedly want to spend some time in each of the major cities en route.

There are so many amazing things to do in all of these locations that the trip could take an eternity to complete if you had that long!

When in Detroit, for those fascinated by the city’s long association with the motor industry, make sure to visit the Henry Ford Museum.

For music lovers, don’t miss the small but perfectly formed Motown Museum.

Buy here the perfect Wisconsin road trip itinerary

14. Madison to Mount Rushmore

Start in: Madison

End in: Mount Rushmore

Distance: 798 miles

If you’re seeking inspiration for road trip ideas from Wisconsin, then why not set out for the world-famous Mount Rushmore?

Should you find yourself in the state’s capital, then this is one of the finest long-distance road trips from Madison, WI. 

Along the route, you can take in La Crosse, Blue Earth, Sioux Falls, and Badlands National Park, before reaching Mt Rushmore, undoubtedly one of the best road trip destinations from Wisconsin.

When you reach your destination, the best place to stay is the nearby town of Keystone, just three miles from the monument.

There are lots of great dining options in the former gold-mining town of Keystone, from where you can book helicopter trips for a different perspective on the monument.

All in all, one of the best road trips from Wisconsin!

Buy here the perfect Wisconsin road trip itinerary

15. Wisconsin Dells to Minneapolis

Start in: Wisconsin Dells

End in: Minneapolis

Distance: 216 miles

If you’re seeking short road trips from Wisconsin, then this 216-mile trip from Wisconsin Dells to Minneapolis is perfect for you.

The journey takes in New Lisbon, Black River Falls, Whitehall, Eau Claire, New Richmond, and Saint Paul, before terminating in the vibrant, arty city of Minneapolis.

On the way, you’ll see a lot of Central Wisconsin and can stop to discover many of the fun things to do in Central Wisconsin.

Minneapolis is a buzzing location with much of the action centered on the city’s rich and varied arts scene.

Around every corner, you’ll be sure to stumble across performing spaces, art installations, and museums showcasing not only local but international talents.

Set alongside the banks of the stunning, gently meandering Mississippi River, there are also beautiful parks, lakes and waterways, and miles of walking and cycling trails.

Buy here the perfect Wisconsin road trip itinerary

As we’ve discovered, Wisconsin road trips come in all shapes and sizes!

Therefore, there’s so much variety for you to choose from when considering road trips in Wisconsin.

So whether you like cities, villages, lakes, countryside, history, architecture, or just about anything else for that matter, then there’s a road trip that is perfect for you.

Short FAQ About the Best Wisconsin Road Trips

Hola! I am Paulina, a fervent travelette who crossed the Atlantic Ocean by Boat HitchHiking. On my blog, you’ll find all the tips to make the most of your holiday. Get ready to enjoy outdoor and sustainable travel like hiking, cycling or sailing. Let’s hit the road together!