12 Epic Midwest Family Road Trips

From gorgeous state parks to charming towns and bustling cities, there’s nothing quite as nostalgic as driving through the American Midwest.

While most travelers to the USA usually target its bustling cities and gorgeous coasts the Midwest still remains pretty overlooked on most visitors’ radar. Still, this gorgeous region of America is definitely worth exploring, especially for those yearning for an epic road trip filled with excitement, majestic vistas, and spots that give you that back-in-time feeling.

From roads that will have you driving through haunted places in Missouri to chasing waterfalls across Ohio, here are a few of the most epic Midwest road trips that need to be on your radar!

12 Epic Midwest Road Trips

1. Chicago to St. Louis on Route 66

On the lookout for the ultimate Midwest road trip? Look no further than the classic Route 66 from Chicago, Illinois to St. Louis, Missouri, which is also known as “The Mother Road”.

USA Midwest Road Trips - Rout 66 Chicago to St Louis Map and collage of images

Route 66 actually starts in Chicago and runs all the way to Santa Monica on the West Coast, but if you don’t want to go the entire way, focusing on the Midwest part of the road trip is enough to experience some of the best it has to offer.

Simply put, there is probably no road trip in the entire USA that is as full of classic Americana as the so-called “King of All Roads”. The Midwest portion between Chicago and St. Louis doesn’t slack when it comes to old-fashioned diners, classic service stations, family owned-cafes, cornfields, sleepy towns, and tons of kitschy landmarks.

Start in Chicago, where you can see all the city highlights like the Sears Tower and the Buckingham Fountain before heading to the corner of Michigan Ave. and E. Adams Street, where you’ll find the iconic “Route 66 Starts Here” sign!

Continue onwards to Lyons and check out the Hoffman Tower. Next, head to Joliet and take some time to visit the Joliet Area Historical Museum before hopping back into the car. Along the way, make a stop in the town of Bloomington, where you can stretch your legs by visiting the emblematic Illinois Route 66 Hall of Fame and Museum.

Other unique sights and landmarks you’ll find along the way are the Railsplitter Covered Wagon and the Watermelon Lincoln Monument in Lincoln, the World’s Largest Ketchup Bottle, the Our Lady of the Highway Shrine, the Soulsby Service Station, and so much more!

Once you catch a glimpse of St. Louis Arch, you’ll know the journey is over, but even then, you’ll still find plenty of incredible things to do in St. Louis to make parting a lil’ easier. For a quintessential Midwest experience (and a great excuse to toast the end of this Midwest road trip), don’t miss out on sipping a few beers at the iconic Anheuser-Busch Brewery.

2. St. Louis to Kansas City

Starting in St. Louis and ending in Kansas City, this route will take you through some of the most culture-filled cities and quintessential wild terrain in the southern part of the Midwest.

USA Midwest Road Trips - St Louis to Kansas City Map and collage of images

Start off in St. Louis, where you can spend the day checking out the iconic Gateway Arch over the Mississippi River and a couple of unique museums. From here, head to the Lake of the Ozarks, where you’ll get to bask in some serious lakeside fun with gorgeous views all over.

The city of Columbia is next on the itinerary, where you’ll get to choose from a ton of different activities ranging from outdoor adventures at the nearby Finger Lakes State Park to an afternoon spent checking out local works of art at the Columbia Art League.

Cap off your Kansas road trip touring Kansas City’s numerous memorials and statues. Then, change the mood at the American Jazz Museum and take a stroll through Kansas City’s 18th & Vine Historic Jazz District to finish one of the best Midwest road trips with a bang!

3. Sault Sainte Marie to Leland Michigan Road Trip

Driving from Michigan’s Upper Peninsula to the Lower Peninsula is a jaw-dropping experience and one of the best drives in the Midwest. Starting in Sault Sainte Marie and ending in Leland, it’s hard to beat the majestic wilderness that you’ll get to gawk at the entire way.

USA Midwest Road Trips - Michigan Map and collage of images

Begin in Sault Sainte Marie, a sleepy town perched between Lake Superior and Lake Huron, an ideal lake vacation spot in the Midwest!

From there, head to Tahquamenon Falls State Park for a chance to spend a few hours gazing at striking waterfalls before heading to St. Ignace to hop on the ferry to Mackinac Island. After exploring the island, get ready to cross the Mackinac Bridge to Michigan’s Lower Peninsula, which is commonly dubbed “the mitten” because of its shape.

A must-visit spot in this area of the Midwest is the Headlands International Dark Sky Park for an unforgettable night of stargazing. If you get lucky, you might even get a glimpse of the northern lights!

After a night spent gawking at the stars, you’ll likely feel a bit hungry, so next on your itinerary is Traverse City, which is considered the foodie capital of Michigan! After gorging on as many dishes as you can, head over to Leland where you can explore Sleeping Bear Dunes National Lakeshore to end this epic Midwest road trip.

Bonus detour: If you have the time, make a small detour by driving the Leelanau Peninsula Wine Trail, where you’ll get to try the local wines at various estates. Can you think of a better way to close out this marvelous road trip?!

Longer to spend in Michigan? Check out some of the best beach towns along the Michigan coast, or our complete collection of scenic driving routes in Michigan

4. Iowa Nature Adventure

Even though the state of Iowa is often overlooked on most Midwest road trips, the Hawkeye State is actually a place that brims with natural gems if you just know where to look!

USA Midwest Road Trips - Iowa Nature Adventure map and collage of pictures from Iowa state parks

Start at Decorah’s Ice Cave, an ice cave you can explore in just a few minutes but acts as a super epic way to begin this Midwest road trip. From there, head over to Dunning’s Springs Park, where you’ll find a striking 200-feet waterfall hidden amid a charming forest.

Next on the itinerary is Effigy Mounds National Monument, which homes over 200 effigy mounds created by Native Americans centuries ago. Although American Indian ceremonial mounds can be found in several locations, Effigy Mounds National Monument harbors many that are shaped like animals!

Another natural highlight deserving a spot in your Iowa road trip is Maquoketa Caves State Park. Here, you can hike and explore tons of caves scattered throughout. Finish your trip at Wildcat Den State Park, where nature and history make a perfect mix that will allow you to hike to stunning geological formations on sandstone bluffs and learn about Iowa’s past at the Pine Creek Grist Mill.

5. Missouri Ghost Town Trail

If you’re a fan of the paranormal, this Missouri Ghost Town Road Trip is sure to please.

This unique scenic road trip will have you exploring some of the most haunted places in Missouri, some of which flourished when Route 66 was opened in 1926 and later abandoned when the interstates were built, and Route 66 was rerouted.

The first stop in this spooky Midwest road trip is Arlington, which was a thriving resort town back in the 1860s before it was forgotten and left to deteriorate. The town of Bloodland is next, which was abandoned during World War II and wiped out from the map, leaving only a church bell. Rumor has it that angry displaced residents have haunted the area ever since!

If you’re feeling brave, continue on I-44 until you find the only remains of Possum Trot, a church and a house that sit quietly eight miles southwest of Nixa, where ghost sightings have been reported time after time.

From here, head west to Monark Springs, a small town that was abandoned after a typhoid outbreak in the 1950s. Finally, end your spooky road trip in Georgia City, where the cemetery is all that remains from the once-prosperous town that thrived in the 1860s.

6. West Virginia Midland Trail

119 miles of pure wild beauty is what the West Virginia Midland Trail is all about.

USA Midwest Road Trips - Midland Trail West Virginia Map and collage of images

Winding through rolling hills, dreamy forests, cascading waterfalls, and idyllic lakes, this scenic byway will take you from one end of West Virginia to the opposite, all while giving you plenty of opportunities to stop and park your car to go on a hike, see plenty of historic sites, and more.

Moreover, there are plenty of farmlands and small towns scattered all over that provide that old country charm. Hico, Ansted, Gauley Bridge, and Mt. Carbons are only some of the spots where you can stop and stretch your legs a bit, grab a bite, or spend the night before hopping back on your car and turning the music back on – preferably John Denver!

7. Milwaukee to the Wisconsin Dells

This is one of the best Midwest road trips for discovering the highlights of Wisconsin, taking you from Milwaukee to Green Bay and ending in the stunning Wisconsin Dells, one of the best family vacation spots in the Midwest.

USA Midwest Road Trips -Milwaukee to Wisconsin Dells map and photo collage

Take in the highlights of Milwaukee from the food and breweries to its history and gallereis – don’t forget the Harey-Davidson Museum before hitting the road.

Following Lake Michigan to Green Bay you’ll pass through scenic towns such as Port Washington. Make sure to stop in at the Heritage Hill State Historical Park – and maybe catch a Green Bay Packers game?

The Wisconsin Dells await next – the kids will no doubt have their wishlist for “the Waterpark Capital of the World“, but there are plenty of other outdoor adventures to enjoy. Make some time for a scenic boat tour and try one of the many wineries, breweries and distilleries.

Devil’s Lake State Park is the perfect way to finish your Wisconsin Road Trip.

8. Iowa Great River Road

The Iowa portion of the Great River Road follows the great Mississippi River from Iowa’s northern to southern borders. Another classic Midwest road trip, this route will take you past beautiful landscapes such as farmlands, forests, and sheer bluffs where tons of eagles soar up high.

USA Midwest Road Trips - Great River Road Iowa Map and collage of images

Along the way, you’ll also find many charming river towns with friendly people and interesting sites worth checking out. Think Al Capone’s hideout – the Julien Hotel in Dubuque – or Le Claire’s famous vintage shops, including the one featured in American Pickers!

Other points of interest along the Iowa Great River Road are Pikes Peak, the National Mississippi River Museum and Aquarium, Eagle Point Park, and the Dubuque Arboretum and Botanical Gardens.

9. Post-Rock Scenic Byway in Kansas

The Post Rock Scenic Byway is a stretch of byway in Kansas that winds through the Smoky Hills and Wilson Lake.

USA Midwest Road Trips - Post Rock Scenic Drive Kansas Map and collage of images

Even though it’s only 18 miles long, this route doesn’t slack in beautiful vistas and amazing points of interest. As a fun fact, the Post Rock Scenic Byway was named after the limestone rock posts used by Native Americans to build their homes and fences back in the day, some of which you can still admire today!

An important part of the Post-Rock Scenic Byway surrounds Lake Wilson, with many options for scenic stops and trails available for hiking in case you want to linger a while. At the end of the road trip, you’ll also get the chance to explore Lucas, an artistic small town that harbors several galleries and the well-known Garden of Eden, which features more than 150 statues!

Check out even more incredible Kansas scenic driving routes and byways over here

10. Old Red-Old Ten Scenic Byway in North Dakota

Running parallel to Interstate 94, the Old Red Trail will show you some of the best North Dakota has to offer, ranging from charming farm scenery to clear blue skies, vintage eateries, and quaint little shops filled with treasures to be found. This road is all about taking your time, driving slowly, and enjoying a ride that will make you feel as though you traveled back in time!

Once you pass Hebron, be on the lookout for the Richardton and Schnell Recreation Area, a 2,000-acre nature preserve where you can hit a few hiking trails in order to explore North Dakota’s unraveled nature. Other must-stops are Assumption Abbey in Richardton and Salem Sue, a giant Holstein Cow fiberglass sculpture.

11. Black Hills & Badlands in South Dakota

This family road trip includes some of the most iconic landmarks of the Midwest, and some of the most scenic drives.

USA Midwest Road Trips - Black Hills South Dakota map and collage of images

A classic South Dakota road trip will see you start in Rapid City before traversing the incredible scenery and rugged beauty of Badlands National Park. Make sure to stop in at Wall Drug before venturing west to the Mammoth Site in Hot Springs.

Wind Cave National Park will be your next South Dakota stop. Explore one of the country’s oldest national parks with its fascinating and complex cave system.

Mount Rushmore, along with Crazy Horse Memorial are undoubtedly going to be your next stops. You can see the Presidents’ heads up close on the 0.6-mile Presidential Trail, a short trail walk, or seek out the overlook on SD-244 to see Washington’s profile from a distance. Come on a summer’s evening to witness “Legends in Light” laser light show on the Crazy Horse Memorial.

Make sure to finish your trip with the Peter Norbek Scenic Byway to experience the Cathedral Spires of Custer State Park, often regarded as one of the country’s best scenic byways.

12. Ohio Waterfall Road Trip

Last but not least, no trip to the Midwest is complete without exploring the stunning waterfalls of Ohio. The Ohio Waterfall Road Trip is the perfect route to take in order to explore the best of them!

USA Midwest Road Trips - Ohio Waterfalls Trail Map and collage of images

Most of Ohio’s finest waterfalls can be found inside state parks, many of which you’ll get the chance to stop at as you drive this Midwest road trip. The Mohican State Park is a must-do stop where you’ll get the chance to see two falls, Big and Little Lyon Falls.

Next on the itinerary, head over to Cuyahoga National Park, where aside from getting plenty of incredible hiking ops, you’ll also get to see the striking 65-feet tall Brandywine Falls. You’ll find the best colors and climate in the fall.

To end your scenic drive in Ohio, drive over to Hocking Hills State Park, which harbors three gorgeous falls and a hiking trail that is commonly ranked as the best in the entire of Ohio!

We hope this list of the most epic Midwest road trips inspired you to grab your car keys, play some Johnny Cash tunes, and hit the road!

More To Know Before Hitting The Road In The Midwest

  • Be careful of your time zones traveling through the Midwest! Michigan, Ohio, Kentucky, and Indiana follow Eastern time, whereas Wisconsin, Illinois, the Dakotas, Iowa, Kansas, and Missouri are in Central.
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Which of these Midwest road trips catch your eye the most? I’d love to know which ones you’re most excited to drive, so let me know all about your plans in the comment section below!

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