Remove Ads

The magical Midwest: Castle ruins, epic dunes, and Badlands

Exploring America's heartland.

  • 15
  • 54:52
  • 3,238 mi
  • $518

Created by Holiday Inn - August 18th 2016

We've spent the past summer partnering with Holiday Inn to find the most epic road trip. To decide on the final route, we had travelers show us their favorite places to visit.

The heartland of America is an incredibly gorgeous region, full of historic sites, mom-and-pop restaurants, beautiful natural wonders, and a few of the quirkiest roadside attractions in the entire country. From the insanely massive Mall of America, to one of the weirdest houses you'll ever visit, this is your guide to finding magic in the Midwest on the most epic road trip route.

Remove Ads

Ha Ha Tonka State Park

Tucked behind lush forests and bordered by a vast river, Ha Ha Tonka State Park is a world unto itself. Ha Ha Tonka allegedly comes from the Native American phrase for “laughing waters”, a reference to the area’s many springs. There are 15 miles of trails for hiking enthusiasts, complete with sinkholes, natural bridges, and even caves. But, the most prominent park feature is the early-20th-century castle ruins.

Robert McClure Snyder was born in 1852. In 1904, he bought 5,000 acres of land around Ha Ha Tonka Lake and Spring. He started building roads and used the area as a place to escape, as he liked to explore the many caves and generally find respite from busy city life. He even began work on a giant stone mansion, which looked just like a castle, where he could live.

Unfortunately, he died before he saw his dream home completed. In 1906, he became one of Missouri’s first automobile fatalities. His sons took over construction on the castle and completed it in the 1920s. The castle was used as a boutique hotel for the next two decades. However, tragedy struck in 1942, when a horrible fire completely destroyed the interior, and the carriage house. In 1976 vandals burned down the water tower. Today, you can still explore what remains of the castle... it's a hauntingly beautiful hike.


St. Louis, MO

The Gateway Arch is an absolute must-visit for anyone passing near St. Louis. It's one of the most famous icons in the Midwest, and as a symbol of America's westward expansion, there's no place more worthy of being the most famous icon for the region. Take a ride to the top of the arch and enjoy the views of both sides of the Mississippi. Be sure to spend some time browsing the fascinating exhibits at the visitor center, too.

American Gothic House

You know the painting American Gothic? The one with the somber looking man with a pitchfork and his daughter standing in front of the quaint house? The artist, Grant Wood, was actually inspired by this home, which appears in the work! There's a neat little visitor center that features films and exhibits on his life and works, and you can borrow costumes and pose as the couple from the painting for a great photo op!

Willis Tower & Chicago Skydeck

Chicago is the biggest city in the Midwest, so it's definitely worth a stop. Take in the Windy City's impressive skyline from atop the Willis Tower (aka Sears Tower)... the second-tallest building in the country. The view from 1,353 feet up spans across the city and out beyond the lake. If you're feeling brave, step out onto one of the glass ledges that lets you look straight down onto the street. Hopefully you're not so queasy after that view that you can't stomach some deep-dish pizza!

The Midwest might not be on the ocean, but it still has some pretty rad beaches. Sleeping Bear Dunes is one of Michigan's best spots to enjoy the lakeshore. It's got swimming beaches, massive dunes for hiking and sand sledding, a gorgeous scenic drive, historic farmsteads, and tons more. You can make an evening of your stop here by camping out. Stargazing and s'mores make for a fabulous end to a day at the beach!

For a more rugged view of the Great Lakes coast, head to Pictured Rocks. Cliffs, waterfalls, and hardwood forest line the edge of Lake Superior, making for some really awesome hiking and boating. Rent a kayak or book a boat tour for an extra-special view of Michigan from the water, or swim in the lake off of one of the beaches!

The House On The Rock - Resort | Attraction | Inn

The House on the Rock is a total hidden gem. The uniquely built building houses a massive collection of the strange and the fascinating. Tour the many rooms filled with antiques, vintage coin-operated machines, a carousel, a sea monster, and tons more, and appreciate the random but well-curated attraction. It's kind of one of those places that you need to experience to fully understand, but go into it with an open mind!

Mall of America

Sure, the Mall of America is pretty touristy, but it's a pretty memorable road-trip stop. For starters, there's something to entertain even the pickiest traveler here: roller coasters, an aquarium, mini golf, arcades, restaurants, bars, and (of course) endless shopping. Even if big touristy attractions aren't your cup of tea, there are some cool local shops, and the people-watching is incredible.


Mitchell, SD

As you drive through the Midwest, it's hard to not notice the nearly endless corn fields across the region. Pay tribute to this seemingly omnipresent crop at Mitchell's Corn Palace! The exterior is decorated with corn kernels, and inside you can find a pretty corny gift shop. Also check out the murals along the side of the building's exterior, which change yearly based on the town's theme.

Wall Drug Store

Wall Drug Store is another quintessential roadside attraction that has its roots in the classic American road trip. It started off as a little, small-town drug store that realized it could bring in tourists road-tripping around the region to Mount Rushmore and the Badlands by offering free ice water. Within a few years, it grew into a full-blown tourist attraction, with kitschy photo ops, multiple restaurants, and loads of cute souvenirs. But, of course, the store still offers free ice water!

Badlands National Park

The Midwest isn't all cornfields... it's also home to the rugged and mysterious Badlands National Park. Grasslands and rolling sandstone hills create an interesting landscape, and the fossils, prairie dogs, and colorful rock formations make this national park an awesome place to hike or take a scenic drive.

Historic Deadwood

If you're looking for a taste of the Wild West, then saddle up and ride into Historic Deadwood! Back in the nineteenth century, Deadwood was known as a notoriously wild settlement where outlaws such as Wild Bill Hickok and Calamity Jane frequented the saloons, and miners gambled away their fortunes. Today, you can see re-enactments of gunfights, toss back drinks in a saloon where bandits drank, play some old-school poker, and see the graves of Calamity Jane and Wild Bill!


Keystone, SD

You can't visit South Dakota and not stop by Mount Rushmore! Admire the sheer size and incredible detail of this patriotic landmark, and learn the crazy history of how this monumental mountain was carved... and what the original plans called for it to look like!


For a totally unique and totally American take on England's Stonehenge, stop by Nebraska's Carhenge. It's one of those random but super-fun stops that's great for a cool, quirky photo op.

Geographic Center of the contiguous United States

End your trip right in the middle of it all! The Geographic Center of the Contiguous United States is in the middle of a field in Kansas, which is kind of symbolic if you think about it... it's actually pretty humble. There's a marker, and a little chapel where you can record your name and your hometown. It's a nice place to watch the sun set across the field and reflect on your adventure!

Remove Ads

The Midwest is full of unexpected surprises: Skyscrapers, beaches, castle ruins, and Wild West towns are hidden among the fields and Badlands of the country's heartland. Oh, and the corn. Lots of corn.

Holiday Inn

We're searching for amazing places across America to create America’s most epic road trip. Get inspired by your fellow travelers’ journeys below, use the link above to share your favorite spots with us, and you can enter to win your next epic journey!

Explore More Trip Guides