13 Best Midwest Road Trips

This guide to the best Midwest road trips was contributed by Kassidy.

Are you looking for some of the best Midwest road trips to plan a vacation close to home this year? The Midwest is one of the most underrated destinations in the United States, and although we don’t have mountains or the ocean, there is so much to explore.

Between the Great Lakes, the gorgeous rolling hills, and quaint small towns, you can easily fill a few days, an entire week, or more with fun activities for the whole family. So, whether you’re looking to explore the great outdoors or immerse yourself in the local culture, the Midwest has something for everyone.

In this post, I’ll share with you the very best places to take a road trip in the Midwest to soak up the beautiful views that this underrated and overlooked region.

Route 66 sign on the road - best Midwest road trips
Best Midwest Road Trips

Best Midwest Road Trips

Below are the best Midwest road trip ideas that you can take for your next vacation, how long you should have to take the trip, and some of the best things to do along the way.

1. Duluth to Grand Portage – Minnesota

Distance: 150 miles
Drive Time: 3 hours
Recommended Time Needed: 5+ days

road trip destinations Midwest - Duluth MN
Which Midwest destinations will you include on your road trip?

The drive between Duluth and Grand Portage follows the shoreline of Lake Superior and provides some of the most beautiful views in the Midwest.

With a start in Duluth, you can wander around Canal Park and watch as ships pass underneath the Aerial Lift Bridge. There are many restaurants, local shops, and more before even leaving the starting point.

After you’ve done enough in Duluth, begin the drive up Highway 61 and the North Shore Scenic Byway, where you’ll find views for the entire way.

Make a stop in the small town of Two Harbors and visit Betty’s Pie, one of the best places for dessert and dinner. Then, make your way into Gooseberry Falls State Park, where you’ll find beautiful waterfalls. Stay a night in Two Harbors to really experience it all!

Further up the highway, you’ll find Split Rock Lighthouse State Park, where you can hike to a lighthouse over Lake Superior, and Tettegouche State Park, which is home to the tallest waterfall in Minnesota.

Grand Marais is just a short distance away and offers plenty of great places to eat, shop, and wander along the shores of Lake Superior. Lutsen is also nearby, which has a great ski resort during the winter months. Many fantastic Minnesota resorts are located on the shores of the lake that are great places to stay.

You can continue further up the road to Grand Portage State Park, which is nearly in Canada. There’s a beautiful waterfall and many hiking trails here.

This is the most beautiful location in Minnesota and offers many opportunities for enjoying the outdoors and nature.

2. Fargo to Theodore Roosevelt National Park – North Dakota

Driving Distance: 330 miles
Drive Time: 5 hours
Recommended Time Needed: 3+ days

Midwest national parks road trip Theodore Roosevelt NP
For a Midwest national parks road trip, you can’t go wrong with Theodore Roosevelt NP

Starting in Fargo, be sure to enjoy all that there is to do in North Dakota’s largest city. Here you’ll find endless places to shop and eat. If you’re visiting during the right season, you might be able to catch an NDSU Bison football game, which is a local favorite.

Make a stop in Scheels and ride the indoor Ferris wheel, grab breakfast at Black Coffee and Waffle Bar, eat dinner at Sickies Garage, and visit the West Acres Mall.

Then, start making your way west along Interstate 94, which is the road that you’ll follow for the entire road trip.

Further along the way, you’ll pass through Bismark, which is North Dakota’s capital city. Just shortly after, keep an eye out for Salem Sue, a giant cow perched high on a hill in the town of Salem.

Continue along the interstate, and you’ll finally arrive in the small tourist town of Medora. Here you’ll find the entrance to Theodore Roosevelt National Park, small shops, local restaurants, and more.

Head into the national park and enjoy the beautiful views of the North Dakota Badlands, the wandering bison, wild horses, and alert groundhogs. There are plenty of hiking trails and places to camp within the national park.

3. Ironwood to Copper Harbor – Michigan

Driving Distance: 160 miles
Drive Time: 3 hours
Recommended Time Needed: 5+ days

fun road trips in the Midwest - Porcupine Mountains
If your road trips in the Midwest take you to MI, check out the Porcupine Mountains

Michigan’s Upper Peninsula, otherwise known as the Keeweenaw Peninsula, is a beautiful stretch of land that juts out into Lake Superior. Following the rugged coastline from Ironwood to Copper Harbor is another of the best Midwest road trips.

Starting in Ironwood, begin your drive along the highway and turn off into Porcupine Mountains Wilderness State Park. Here you’ll find rolling hills, gorgeous lakes, waterfalls, and plenty of hiking trails. The Upper Peninsula (UP) is particularly beautiful in the fall months!

A stop in Houghton will allow you to learn more about the culture and beauty of this area. You can actually reach the remote Isle Royale National Park from Houghton. Although difficult to get to, if you have the extra time, this is a must!

Once you’ve made it to Copper Harbor, you’ll be in the northernmost city in Michigan and can spend some more time on Lake Superior. Head out on a kayak, visit the local state park, and go for a hike.

If you have more time to spend in the UP, consider checking out Pictured Rocks National Seashore and Marquette.

4. St. Croix Scenic Byway – Minnesota

Driving Distance: 130 miles
Drive Time: 2 hours
Recommended Time Needed: 3+ days

best midwest road trips St Croix Byway
St Croix Byway is a beautiful place to include on a Midwest road trip

Starting in Askov, Minnesota and working its way south toward Point Douglas is the beautiful St. Croix Scenic Byway. This stretch of road is nearly 130 miles long and follows the stunning St. Croix River Valley.

As one of the most gorgeous parts of Southern Minnesota, this Midwest road trip can be completed in as little as 3 days.

Make your first stop in Taylors Falls, where you’ll find Interstate State Park, home to many glacial potholes and hikes along the river. You can even hop aboard a boat and take a scenic dinner tour down the river.

Taylors Falls is also home to Wild Mountain, which features a great water park, an alpine slide, and a ski resort. Many great local campgrounds are also found here for time spent outside.

Continue along the road and enjoy the views for the entirety of the drive, and make your next stop in Stillwater. This gorgeous town has viewpoints of the river, plenty of local restaurants and shops, and a historic lift bridge to cross.

There are several other towns to stop at along the way, but the next of note is Afton, which features Afton State Park and the popular Afton Alps Ski Resort.

If you have a bit of extra time, continue heading south along the highway towards Red Wing, Wabasha, and Winona.

5. Custer to Badlands National Park – South Dakota

Driving Distance: 90 miles
Drive Time: 2 hours
Recommended Time Needed: 5+ days

midwest road trip itinerary Custer State Park
Visit Custer State Park on your Midwest road trip itinerary

While this is one of the shortest drive times on this list, a visit to Custer and Badlands National Park will take quite a few days to really experience it all.

Starting in Custer, you’ll get to experience the best state park in South Dakota. Filled with towering rock formations, roaming bison, and beautiful landscapes, this is a must-see Midwest destination.

In the park, be sure to drive along the Needles Highway, see Sylvan lake, make the hike to Black Elk Peak, and keep an eye out for wildlife.

Before leaving to head to your next stop, you may want to backtrack a bit and visit Wind Cave National Park, where you can wander through one of the world’s most complex caves.

Then, you can begin heading towards Badlands National Park, but be sure to stop at the Crazy Horse Memorial and Mount Rushmore National Memorial along the way. The small town of Keystone also feels like an old western town and is perfect for grabbing lunch or wandering through the shops.

Lastly, finish your trip with a few days in Badlands National Park. Here you’ll find lots of hiking trails that lead you through the rolling hills and prairies of South Dakota. Beautiful rock formations are the main attractions here!

>>Read: Where to Stay on Your American Southwest Road Trip

6. Chicago to St. Louis – Illinois & Missouri

Driving Distance: 300 miles
Drive Time: 4.5 hours
Recommended Time Needed: 5+ days

road trip destinations Midwest - Chicago skyline
Chicago is a great city to include on your Midwest road trip

The drive from Chicago to St. Louis stretches all the way across the state of Illinois, down into the eastern side of Missouri. This route follows the start of Route 66, one of the original highways in the United States.

Starting in the largest city in Illinois, Chicago, you can experience all that there is to do in the Windy City. First, check out the iconic metal bean in Millennium Park, try some of their famous deep dish pizza, and visit the Art Institute of Chicago.

After you’ve done everything in Chicago, backtrack slightly to visit Indiana Dunes National Park, which lines the shores of Lake Michigan. Then start to head towards Springfield.

In Springfield, be sure to stop at the Abraham Lincoln Presidential Library and Museum to learn more about the most famous resident to call Springfield home. The Washington Park Botanical Garden is beautiful, and there are more places in the city to learn about President Lincoln.

Continue making your way towards St. Louis, and once you’ve arrived, head to Gateway Arch National Park. You can also visit Six Flags St. Louis for a thrill, catch a St. Louis Cardinals game, or check out the city’s great nightlife.

The journey from Chicago to St. Louis is filled with adventure, history, and delicious food, making it a memorable road trip for all.

7. Wisconsin Dells to Bayfield – Wisconsin

Driving Distance: 300 miles
Drive Time: 5 hours
Recommended Time Needed: 5+ days

road trips in Midwest - Bayfield WI
Bayfield, WI is one of the more scenic Midwest road trip destinations

Wisconsin Dells is the water park capital of the world, with over 20 different indoor and outdoor water parks to enjoy! A few favorites are Noah’s Ark, Mt. Olympus, and Kalahari Indoor Waterpark.

Also found in Wisconsin Dells is the Witches Gulch Trail, which is a beautiful gorge that you take a boat to and then wander through the gorge. Devil’s Lake State Park is also just a short distance away for outdoors lovers.

The next stop on your drive is Eau Claire, which is a large city known for its namesake University. Grab a bite to eat here, do some shopping, and hop back on the road.

Along the way, consider stopping at one of the many lakes or waterways or a small town for a snack, and then make the long drive up to Bayfield.

Bayfield is one of the most beautiful places in Wisconsin, with access to the Apostle Islands. Within the small town, you can check out the Bayfield Maritime Museum or shop at the local boutiques on Rittenhouse Avenue.

Then be sure to head to the Apostle Islands National Lakeshore, where you can find trails along Lake Superior, providing some of the most magical views.

If you have some extra time, rent a sea kayak from a local outfitter and head out to the islands themselves. You can also take a shuttle out to the island to spend some time exploring. Or take the ferry over to Madeline Island, the biggest of the Apostle Islands.

8. St. Louis to Joplin – Missouri

Driving Distance: 300 miles
Drive Time: 4.5 hours
Recommended Time Needed: 4+ days

best road trips in Midwest USA - St Louis skyline
A Midwest road trip on Route 66 should include St Louis

If you’ve completed the portion of the Midwest Route 66 from Chicago to St. Louis, then consider continuing on this road trip and completing the rest of the Missouri portion!

Stretching from St. Louis to Joplin, Missouri, this is where the Route 66 highway continues into Oklahoma and ventures out of the Midwest.

In St. Louis, check out the Gateway Arch National Park, attend a St. Louis Cardinals game, and check out all of the great places to eat. You can venture into Forest Park for some time outdoors, or bring your kids to the Magic House for some educational play.

As you work your way further southwest, make a stop in Springfield, Missouri, not to be confused with Springfield, Illinois. In Springfield, you can visit the Route 66 Visitor Center, wander underground and see the unique caverns, and see the Wonders of Wildlife National Museum.

The Ozarks also cover this region, so you can wander through the stunning mountainous region, float down the rivers, or go for a hike.

Continue on until you’ve reached Joplin, where you can see the magnificent Grand Falls or see the Bonnie and Clyde Joplin hideout.

Along the entire drive, you might see signs that read ‘Route 66,’ so be sure to stop at one or a few and snap your photo!

>>Read: Itinerary for 3 Days in Charleston, SC

9. Wisconsin’s Great River Road – Wisconsin

Driving Distance: 250 miles
Drive Time: 5 hours
Recommended Time Needed: 4+ days

Midwest road trip ideas - La Crosse WI Mississippi River
There are lots of pretty road trip destinations on the Mississippi River

The Great River Road in Wisconsin travels along the Mississippi River for about 250 miles, providing phenomenal views and great places to stop.

Starting in the small town of Prescott and working its way south to the town of Kieler, you’ll pass through over 30 small, historic towns on this route.

There are so many great activities to do along this road, from hiking to biking to fishing and just enjoying the scenic overlooks. You’ll find scenic overlooks in Cassville, Bagley, La Crosse, Alma, and more. They all look into the Mississippi River.

The Great River State Trail is a paved bike path that follows the road, which makes for a perfect spot to get out and enjoy the sites from the great outdoors. You can also hike or bike in many of the adjacent state parks.

You can boat along the river, or take a boat tour to take in all of the bluff views from a whole new perspective. People also enjoy fishing the waters of the mighty Mississippi.

As you drive the road, you can also cross over into Minnesota and visit small towns such as Red Wing, Wabasha, and Winona.

10. Chicago to Grand Rapids – Illinois, Indiana, & Michigan

Driving Distance: 180 miles
Drive Time: 3 hours
Recommended Time Needed: 3+ days

USA Midwest road trips itinerary - Indiana Dunes NP
Indiana Dunes National Park is a fantastic place to visit on a Midwest road trip itinerary

Get ready for a scenic adventure through the Midwest with a road trip from Chicago to Grand Rapids, Michigan. Start your journey in the Windy City and be sure to check out some of the best activities here. From The Bean in Millennium Park to the Skydeck Chicago observation deck and the Navy Pier, there is plenty to do.

From there, start making your way around the great Lake Michigan towards Grand Rapids. Stop at Indiana Dunes National Park for some time along the lake just after you leave Chicago.

You can choose to either continue following the lake and enjoying the views of the magnificent Great Lake, or you can venture inland a bit and go through Kalamazoo.

Either way, you’ll wander through many of Michigan’s small towns, and you can make stops in any of them to grab a bite to eat or stop in the local shops.

Once you’ve made it to Grand Rapids, enjoy all that there is to do in Michigan’s second largest city. Depending on the season, you can find plenty to do from checking out local breweries to checking out the Grand Rapids Public Museum or the Frederik Meijer Gardens and Sculpture Park.

The journey between these two large cities is short, but another great option for exploring the Midwest on a road trip.

11. Sleeping Bear Dunes National Lakeshore to Mackinac Island – Michigan

Driving Distance: 150 miles
Drive Time: 3 hours
Recommended Time Needed: 4+ days

road trips in the Midwest - Sleeping Bear Dunes Glen Arbor
You won’t be disappointed by the scenery at Sleeping Bear Dunes

These two beautiful Michigan destinations make the perfect Midwest road trip when paired together, because they aren’t too far from one another. It could even be done in just a weekend if you were running short on time.

Starting near Sleeping Bear Dunes National Lakeshore in Glen Arbor, explore this beautiful area before starting your journey to the northern tip of Michigan.

Lining the shore of Lake Michigan, you’ll find the Sleeping Dunes. These giant sand dunes sit up against the shores of the Great Lake, and create an incredible contrast against the blue water. You can spend time just admiring the dunes, or you can climb then.

Several hiking trails surround the area, and you can also find great places for camping.

After you’ve spent enough time at the dunes, start making your way east, before cutting north towards Mackinaw City and Mackinac Island.

While technically reachable year-round, it’s best to visit Mackinac Island during their busy times, from May to October, because the wind off of the lake can get very cold.

The small, historic island can be reached via ferry. Once you’ve arrived, explore the state park, visit Arch Rock, try the famous Mackinac Island fudge, visit the historic downtown, and more.

>>Read: What to Pack for a Trip: Travel Packing Checklist for Carry-On Only

12. Glacial Trail to Loess Hills Scenic Byways – Iowa

Driving Distance: 100+ miles (depends)
Drive Time: 3+ hours (depends)
Recommended Time Needed: 3+ days

country road in Iowa - USA Midwest road trip ideas
Where will the road take you?

While Iowa is often forgotten about when it comes to traveling the Midwest, there are a few great places in the state to visit.

Glacial Trail and Loess Hills Scenic Byways are two beautiful places in western Iowa, where you can drive around the scenic routes and take in the views.

The Loess Hills start around Akron, Iowa and make their way south into Missouri and parts of Nebraska. You can follow this route and see all of the beautiful rolling hills, blooming wildflowers, and hiking trails for as long as you want.

The Glacial Trail Scenic Byway is a loop that has views of rolling hills and bluffs, which are a rare sight in Iowa. It starts near Peterson and loops around to Linn Grove.

Pairing the two of these scenic drives together makes for a great road trip that allows you to experience some of Iowa’s unseen beauty. The distance of the trip will depend on how far you choose to drive it.

13. Toledo to Cleveland – Ohio

Driving Distance: 120 miles
Drive Time: 2 hours
Recommended Time Needed: 2+ days

Cleveland skyline - Midwest road trips destinations
Cleveland is an underrated road trip destination in the Midwest

Looking for a road trip in the Midwest that can be done in just a weekend? Then check out this route from Toledo to Cleveland in Ohio.

Following along Lake Erie, you can take in the views of this Great Lake for the entire drive, and make some stops along the way.

First in Toledo, check out the Toledo Museum of Art, the Toledo Botanical Garden, and more. Then start heading towards Cleveland.

Once in Cleveland, consider heading south a but to Cuyahoga Valley National Park for some hiking and exploring the waterfalls and gorges. You can also check out the Cleveland Museum of Art and the Rock & Roll Hall of Fame.

While just between two cities, this road trip can lead you through some beautiful and unique places!

Midwest Road Trip Itineraries

The Midwest is unsuspecting, and many people consider it a “fly over” region of the United States that isn’t worth stopping by.

But if you actually get out and explore it on a Midwest road trip, then you’ll see that it’s much more than that, and is actually a beautiful location to visit!

From the rolling hills of South Dakota to the lake shores of Minnesota and the water parks of Wisconsin, there’s something for everyone on one of these road trips through the Midwest.

About the author: Kassidy is a Minnesota native who enjoys spending her time exploring her home state and the surrounding areas. Her favorite part of Minnesota is the North Shore, and she loves sharing about her adventures on her blog, Kassidy’s Journey.

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This list of the best Midwest road trips will give you lots of ideas for destinations in the Midwest to include on a fun road trip.
This list of the best Midwest road trips will give you lots of ideas for destinations in the Midwest to include on a fun road trip.