Northern Minnesota is a treasure trove of natural beauty. This quick road trip will take you along the shore of Lake Superior on Minnesota State Highway 61.

7. Chicago to St. Louis Along Route 66

This classic road trip is really one for the books. It’s recommended to take at least 7-10 days to drive through The Black Hills in South Dakota, simply because there is so much to see.
Starved Rock State Park is located in the quaint and historic Utica, Illinois

  • Chicago: You cannot start your trips in Chi-town without going on a boat architecture tour or at least spending part of your day exploring the Art Institute of Chicago.
  • Starved Rock State Park: In the small town of Utica, you can find hiking trails that lead to canyons and waterfalls. The park is beautiful all year round (yes, even in the winter when the waterfalls freeze!), but the best time to go is in the fall when the leaves are changing color.
  • Pontiac, Illinois: Home to the Route-66 Hall of Fame and Museum, this town is full of Route-66 memorabilia and murals. Make sure to take a picture with the World’s Largest Covered Wagon while you’re there!
  • Springfield, Illinois: If you want to break up the 4 1/2 hour drive, this is an excellent overnight stop. As Illinois capital, Springfield is home to plenty of historic sites, including the childhood home of Abraham Lincoln.

6. Davenport, Iowa to Omaha, Nebraska

One of 13 caves at Maquoketa Caves State Park, Iowa

Check out our full South Dakota road trip itinerary here!

  • Maquoketa Caves: Before getting too far west, a short detour will take you to Maquoketa Caves State Park, home to a 1,100 foot “dancehall cave” and a 17-ton “balanced rock”.
  • McIntosh Woods State Park: Visitors can “glamp” in a yurt right on Clear Lake. Make sure to reserve your yurt ahead of time, as they are very popular and book fast!
  • High Trestle Trail: 28-miles of trails to explore, along with some impressive bridges.
  • Lover’s Leap Swinging Bridge: An 8-story high bridge which has some great views.
  • Stony Creek Hotel: The last Frank Lloyd Write hotel in the world–a great stop for architecture enthusiasts.

5. St. Louis to Kansas City, Missouri

Kick off your trip with a visit to the St. Louis Botanical Garden!

Ah, Wisconsin. The land of cheese curds, Blue Moon beer, and ultra-enthusiastic football fans. Sounds like the perfect place to kick off a road trip, right?

  • City Museum in St. Louis: Check out this art installation-meets-adult playground that is made of salvaged architectural objects.
  • Lake of the Ozarks: This is a region of Missouri full of hiking trails, ponds, and lakefront fun. Go on a cave tour and see the impressive limestone formations or simply spend a day on the lake basking in the sun.
  • Columbia: Make sure to stop at Rock Bridge State Park and Finger Lakes State Park for hiking, biking, and more outdoor fun. Looking to stay indoors? Spend an afternoon at the Columbia Art League checking out the local art or even taking a class.
  • Kansas City: Don’t miss out on the legendary jazz scene by first checking out the American Jazz Museum and maybe even catching a live show in the evening. Can you think of a better way to close out this epic road trip?

4. The Black Hills in South Dakota

Can you spot Washington’s profile?

  • Badlands National Park: Drive the scenic 39-mile loop, which boasts 16 amazing overlooks. The park itself has plenty to do and see, making it the perfect place to start your trip.
  • Wind Caves National Park: Adventurous souls can explore what unique rock formations lie within the caves.
  • Hot Springs, South Dakota: Ten minutes away from Wind Caves you can find not only some awesome hot spring attractions but also one of the world’s greatest fossil treasures, a mammoth sinkhole.
  • Mt. Rushmore: A bucket-list road trip stop, along with the Crazy Horse Memorial. A short 0.6-mile hike will take you closer to the president’s faces, but a more rare site is the overlook on SD-244 where you can see Washington’s profile.

3. Milwaukee to Wisconsin Dells

This is the kind of view you can expect on any of the tours of the Dells on the Wisconsin river.

Both of these Midwestern cities are stellar destinations in themselves, but there is plenty to see in between while driving along the original Route 66 (now I-55).

  • Milwaukee: This city is known for having some of the best breweries in the country, so if you’re a beer-enthusiast make sure to check out Lakefront for a tour. The city is also home to the oldest bowling alley in the United States and a haunted concert hall that is a must-visit for music fans.
  • Madison: Experience its many lakes–you can even take a tour to learn more about how organizations are working to keep them clean!
  • Eugster’s Farmers Market: If you want to get a taste of the best produce that Wisconsin has to offer, head 15 minutes south of Madison to Eugster’s. The market isn’t open in the winter, but does have produce available in the spring, summer and fall.
  • House on the Rock: Located in Spring Green, this is an eclectic maze-like interactive museum with surprises at every turn.
  • Wisconsin Dells: Take a tour either by house and carriage, boat, or the famous Wisconsin “ducks“.
  • Devil’s Lake State Park: Get out for an epic hike or go kayaking and canoeing at Mirror Lake State Park, which is close by.
  • International Crane Foundation: Check out the cranes and learn more about conservation efforts in the area.

2. Michigan – The Mitten to the UP

Whether you’re from the Midwest or have been curious about traveling there, we hope this list inspires the road tripper in you to get out and explore. Who knows, maybe you’ll discover your new favorite hiking trail, camping spot, or quirky small town!
Pictured Rocks National Lakeshore

Take Interstate 80 from Davenport to Omaha and you’re sure to find plenty of hidden gems. Ever wondered where the world’s largest truck stop is? Yep, it’s in Iowa, right on I-80!

  • New Buffalo: Close enough to Chicago to be convenient for city-dwellers but far enough to feel like another world, this town is minutes away from Warren Dunes State Park and has a neat European Farmer’s Market that locals love.
  • Sleeping Bear Dunes: Located right outside beautiful Traverse City, spend a day (or two!) hiking any one of the trails at Sleeping Bear.
  • Ocqueoc Falls: Before you head to the Upper Peninsula, consider resting for the night at Ocqueoc Falls State Forest Campground where picturesque waterfalls await you.
  • Canyon Falls: Known as Michigan’s own version of the Grand Canyon, this breathtaking waterfall is situated south of L’Anse, off US 41 in the Upper Peninsula.
  • Pictured Rocks National Lakeshore: The Upper Peninsula has plenty of natural wonders to explore, including the various scenic sites at Pictured Rocks National Lakeshore.

1. Minnesota’s North Shore

St. Louis is a Midwestern hub of art and culture in itself, making it a great launching point for an epic Missouri road trip.
Palisade Head is a great place to take in the sites and maybe even level-up your Instagram game!

The Midwest is known for a few things: ranch dressing (yep, even on pizza!), cornfields, and super friendly people. If you haven’t thought about taking a road trip in the Midwest, our top 7 midwest road trip picks will have you packing up your vehicle for your next adventure:

  • Tettegouche State Park: Located near Silver Bay is the picturesque Tettegouche State Park, which boasts stellar waterfalls, hiking, rock climbing, and year-round camping.
  • Split Rock Lighthouse: A must-see location famous for its history, Split Rock is another North Shore destination that showcases the beauty of Lake Superior.
  • Palisade Head: Just an hour north of Deluth, you’ll find this 932-foot high cliff towering over Lake Superior which attracts plenty of site seers as well as rock climbers.
  • Gunflint Scenic Byway: If you want to take a detour and extent your trip a bit longer, consider taking this scenic route. It’ll take you through the Superior National Forest where you can find short offshoots that lead to campgrounds, lakes, and places to canoe.

Michigan is brimming with outdoor activities and hidden gems. From as far south as the Indiana border to as far north as the Canadian border, you can find a wealth of natural wonders and eclectic small towns that make Michigan a magical road trip destination.

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