4 Best Midwest Road Trips in the US

How Much Do You Know About The Midwest?

What’s YOUR annual summer ritual? For some, it may be loading the car with the kids and snacks for the drive to Florida to bask in the sunshine.

While for others, it might be setting out for the unknown, with the opportunity for discovery and adventure around the next turn. After all, when the desire to travel strikes, hitting the road is the most spontaneous way to get your fix.

Even just a weekend trip can refresh your mindset. Well, for those craving adventures, the Midwest offers a variety of landscapes ripe for exploration with a classic road trip.

From rolling vineyards to lush river valleys, high limestone bluffs to some pretty great lakes, this region of our country is often overlooked. But we’ve decided it was time to change that.

So cue up a playlist, pack your favorite snacks, and hit the road on one of these 4 Midwestern road trips, sure to highlight the best of America’s vibrant heartland.

Chicago to St. Louis Along Route 66

Both of these Midwestern cities are fantastic destinations to visit. But there’s plenty to see in between while driving along the original Route 66, otherwise now known as I-55.

Here’s the route we recommend: You can’t start your trip in Chi-town without going on a boat tour or at least spending part of your day exploring the Art Institute of Chicago. Next, drive to the small town of Utica, where you’ll find Starved Rock State Park.

Here, you’ll find hiking trails that lead to stunning canyons and picturesque waterfalls. The park is beautiful all year round. But the ideal time to go is autumn when the leaves change their colors.

After that, we go to Pontiac, Illinois: Home to the Route-66 Association of Illinois Hall of Fame and Museum. This town is full of Route-66 memorabilia, so make sure you take a picture with the World’s Largest Covered Wagon while you’re there!

Finally, go to Springfield, Illinois. This is an excellent overnight stop. As the capital of Illinois, Springfield is home to many historic sites, including the home of Abraham Lincoln during his younger years.

Lake Michigan To Brown County To Get The Best of Indiana

Start your midwest journey at the 15,000-acre Indiana Dunes National Park in the northwest part of Indiana. This area is situated on Lake Michigan’s beautiful southern shore, perfect for birding, relaxing on the beach, and many other natural activities.

From here, keep driving to the small lake town of Winona Lake to stroll through the little boutiques along the waterfront. If you want an upscale bite to eat, stop into Cerulean, and for a more laid-back vibe, go to the Boathouse Restaurant.

Spend your night just two hours south at The Alexander in downtown Indianapolis, the capital and largest city in the state.

Explore the city using the renovated Canal Walk, visit the acclaimed Indianapolis Children’s Museum, scope out some street art, and enjoy a meal at St. Elmo Steak House.

For some exercise in the city, hike the Monon Rail Trail, a former rail line stretching from Indy to the northern suburbs. After your time there, drive south to Bloomington, home to Indiana University.

This midwest college town offers a picturesque campus and a beautifully walkable downtown area. Continue to Brown County State Park, the largest in Indiana, open for horseback riding, hiking, rock climbing, and so much more.

Discover The Road From Davenport, Iowa to Omaha, Nebraska

While visiting the midwest, if you travel down I-80 from Davenport to Omaha, you’ll surely find lots of hidden gems. Fun Fact: The world’s largest truck stop can be found in Iowa, right on this interstate!

But before going too far west, a short detour will take you to Maquoketa Caves State Park, home to a 1,100ft “dancehall cave” and a 17-ton “balanced rock.” We promise the views will be well worth your stop. Next up, head to McIntosh Woods State Park.

Visitors here can “glamp” in a yurt right on Clear Lake. Just make sure to reserve your yurt ahead of time because they’re very popular, and book up fast!

After this, we suggest outdoor enthusiasts check out High Trestle Trail, a rail trail running from Ankeny to Woodward in central Iowa. You’ll be greeted with 28 miles of nature trails to explore, along with some awe-inspiring bridges.

And while we’re on the subject of bridges of the midwest, Columbus Junction offers up Lover’s Leap Swinging Bridge. It’s an 8-story high bridge with incredible views that shouldn’t be missed.

Need a place to spend the night? May we suggest: The Historic Park Inn? It’s the last Frank Lloyd Wright hotel in the world. This would be an excellent stop for architecture enthusiasts.

Minnesota’s North Shore: Duluth to Grand Portage

On this drive, you’ll get to see the scenic State Highway 61 for 150 miles along Lake Superior’s breathtaking, rocky shores. The route is part of the Arrowhead Region in northeast Minnesota, which, in our humble opinion, belongs on all US midwest road trip bucket lists.

Begin your journey in Duluth, which is famous for its breweries and its native Bob Dylan, who was born in the city. Walk along Bob Dylan Way for a peek into the life of the folk music legend.

Unwind by sipping some artisan spirits at Vikre Distillery, and enjoy the views of the famous Aerial Lift Bridge. To pay tribute to the region’s Scandinavian roots, try Vikre’s aquavit, also known as “Norwegian Everclear.”

For an overnight stay, consider checking the options in beautiful Two Harbors. This town is an ideal spot for exploring Gooseberry Falls, Minnesota’s most visited state park, and Split Rock Lighthouse, one of the most photographed spots in the state.

Midwest road-trippers should also plan to leave some room for pizza at longtime favorite Sven and Ole’s in Grand Marais. From roughly May to October, intrepid explorers can consider an extension to Michigan’s remote and gorgeous Isle Royale National Park.

Daily ferry transport is available from Grand Portage, Minnesota, the scenic endpoint of this North Shore excursion.

No matter which midwest route you decide to take, be sure to pack your camera to capture all your amazing adventures!

And once you’ve had enough of your midwest road trip, why not book a few river cruises? Check out your options here!