Road Trips Midwest: The Best Road Trips in America's Heartland

From hip, art-packed cities to vast landscapes roamed by bison, these road trips Midwest will have you looking at America's heartland in a whole new light

Pandemic or no pandemic, nothing beats the Great American Road Trip. Whether cruising California’s coastal Highway 1 or getting your kicks on Route 66, America’s love affair with the road trip is well known and well documented. But don’t leave the Midwest out of the equation when it comes to epic tales of glory from the road.

Offering everything from quiet lakeside towns and stunning coastal beaches to hip art-packed cities and vast landscapes roamed by bison, these Midwest road trips will have you looking at America’s heartland in a whole new light.

Road Trip to Lake Geneva, Wisconsin

Credit: Travel Wisconsin

This popular vacation destination just an hour-and-a-half from Chicago makes a worthwhile road trip any time of year, although crowds are heaviest in the peak summer season. Those who can’t wait to cross the Wisconsin border before getting in some R&R can stop off along the way at Illinois Beach State Park, quietly perched along the shores of Lake Michigan just south of the state line.

Once in Lake Geneva, a stroll through its always buzzing downtown is a good way to get oriented before making your way to more out-of-the- way destinations – like classic old-school restaurant Mars Resort on nearby Lake Como or Pier 290 in the adorable hamlet of Williams Bay.

Whatever you do, make sure to stroll the public trail that winds its way in spectacular fashion across the entire lake, and hop aboard a boat tour for some breezy local history with cocktail in hand.

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Where to Stay in Lake Geneva

Another option also situated in an excellent location near downtown is Mill Creek Hotel – a less opulent, but no less appealing option for those looking to be near the action. With basic apartment-style rooms offering everything you need and nothing you don’t, you’ll feel right at home settling in for the night listening to sounds of the babbling brook from the White River, which winds its way through the adjacent Samuel Donian Wetland Preserve.

Mill Creek Hotel

Top rated
Lake Geneva
9.2 Excellent (2213 reviews)

Road Trip to Door County, Wisconsin


Nestled on a scenic peninsula surrounded by shimmering blue water, with an abundance of nature preserves and more than a dozen charming small towns, one of the Midwest’s top attractions is also one of its most favored road trip destinations. The three-hour drive from Milwaukee can be broken up with a pit stop in the coastal community of Sheboygan on Lake Michigan, where a festive boardwalk unfurls a number of lively bars and restaurants, such as the 1920s-styled Harry’s Prohibition Bistro.

Once in Door County, you’ll find plenty to keep you occupied – from ferry excursions to remote islands and quiet beachside state parks to hikes through pristine forest and strolls amidst historic architecture. Newport State Park and Schoolhouse Beach on Washington Island are not to be missed, but there’s also nothing wrong with pointing the car into the farmland and seeing where you wind up.

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Where to Stay in Door County

Sister Bay is one of the most happening towns in Door County, and the Country House Resort covers all your bases with affable rooms tucked away amidst 27 secluded acres overlooking the water. The “casually elegant” resort is something of a hidden gem, ideal for families or couples in search of some understated romance.

Country House Resort

Sister Bay
9.6 Excellent (807 reviews)

Another Accommodation Option in Door County

The Waterbury Inn in the almost unbelievably quaint town of Ephraim is an extremely traveler-friendly spot, offering condominium-styled accommodations that are clean, cozy, and comfortable. A variety of activities are on offer, from the inn’s two pools and ping pong room to its picnic areas and bean bag toss.

Waterbury Inn

9.0 Excellent (789 reviews)

Road Trip to Galena, Illinois


History buffs and fans of small town charm will discover more than their fair share of both in the classic road trip destination of Galena, perched along the Mississippi River just east of the Illinois-Iowa border about halfway between Chicago and Des Moines.

Travelers coming from the Iowa capital can break up the 3.5-hour drive with a pit stop in the vibrant college town of Iowa City, home to the University of Iowa and a number of famous authors. Grab a burger with the local crowd at the no- frills George’s Buffet before pushing over the Mighty Mississippi into Galena.

The former home of Ulysses S. Grant is packed with historic mansions perched among scenic rolling hills, but Galena’s number one attraction is easily its amazingly stuck-in-time downtown. The immaculately preserved downtown district is nothing short of a thrill to behold, best explored by bright red trolley or on your own two feet as you pass eye- catching landmarks like the historic Desoto House Hotel. Get out into nature with a kayaking excursion along the Galena River or hit the ski slopes overlooking the Mississippi at nearby Chestnut Mountain.

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Where to Stay in Galena

For accommodations, it’s hard to find fault with the Lefevre Inn. The local classic set back amidst the scenic rolling farmlands of the Galena countryside makes an ideal escape for those in search of cozy wood- burning fireplaces, comfortable B&B-styled rooms, and stellar sunsets. Do some paddle boating on the property’s small lake, explore the surrounding hiking trails, or just cuddle up at the fire pit with a bottle of wine and some S’mores.

Lefevre Inn And Resort

9.6 Excellent (1001 reviews)

Road Trip to Traverse City, Michigan

Located about two hours from Grand Rapids and four hours from Detroit, Traverse City makes excellent use of its natural geography. Sitting in the area of the pinky finger in Michigan’s mitt, the storied road trip town offers unparalleled views of the serene Grand Traverse Bay at seemingly every turn.

But before you get there, a side trip to Sleeping Bear Dunes National Lakeshore (about 30 miles west of town) might be one of the best decisions you’ve ever made in life. With giant sand dunes overlooking pristine Lake Michigan waters, the beauty of this magical oasis is impossible to overstate.

Once in Traverse City, you’ll discover a foodie-focused town surrounded by lush nature and pristine beaches, providing the perfect opportunity to dive into some local culture at top-rated restaurants like The Cook’s House. The pedestrian-friendly community boasts attractions like the historic State Theatre and City Opera House, but no one would blame you if you spent the day posted up at one of Traverse City’s numerous beaches, such as Clinch Park and Bryant Park Beach.

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Where to Stay in Traverse CIty

The Bayshore Resort is a beehive of activity in Traverse City – a Victorian-styled local landmark offering tasteful and well-appointed hotel-style rooms with amenities like a private beach and on-site boat rentals in the summer. No trip to Traverse City is complete without spending some time on the water, so you’ll certainly want to take advantage.

Bayshore Resort

Traverse City
8.0 Very good (32 reviews)

Road Trip to Duluth, Minnesota


This underrated outpost assembled along Lake Superior (just west of the Minnesota-Wisconsin border) is a two-and-a-half hour drive from Minneapolis, but might as well be its own world. They just don’t make towns like this anymore, a fact that becomes readily apparent to anyone lucky enough to discover this small city of 85,000.

But before you get here, a side trip along scenic Highway 61 overlooking Lake Superior (the inspiration for Duluth native Bob Dylan’s classic album Highway 61 Revisited) is basically required. Crank up the radio and enjoy the views.

Duluth may not be the most beautiful town in America, but there’s no denying it’s got character. The former shipping town retains an air of its more gritty industrial past while making travelers welcome with a steady stream of top-tier restaurants, trendy boutique shops, and — of course — a thriving local music scene. Snap some photos of the iconic Aerial Lift Bridge and enjoy a relaxing day in Canal Park before settling in for the night.

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Where to Stay in Duluth

To best take advantage of all that Duluth has to offer, it’s time to try something a little different. A stay at Hostel Du Nord is the perfect way to do so. The hip, stylish spot is a far cry from the grungy hostels of your European backpacking nightmares, offering a more posh take on the traditional hostel experience paired with an endless assortment of activities. Spend the day exploring Duluth on the hostel’s popular brewery tour before relaxing in their steam-heated sauna. Yes, that’s right – this hostel has a sauna.

Hostel du Nord

8.8 Excellent (404 reviews)

Road Trip to Black Hills, South Dakota


There’s nothing really close to Rapid City, South Dakota – and that’s kind of the point. Located five hours west of Sioux Falls, Rapid City is perched at the edge of South Dakota’s iconic Black Hills and within spitting distance of a number of famous destinations from Mount Rushmore to Sturgis. But even if you’re not pulling into town on a Harley, a side trip into the nearby Custer State Park offers a wealth of rewards – from wild bison sightings to dreamy Old West landscapes, as the Midwest transitions into the mountain West.

While you are most likely here to experience the stunning natural beauty of the Black Hills and the myriad scenic drives that dominate the area, there is a surprising amount in Rapid City to keep your attention. The hip Art Alley makes for a classic Instagram backdrop for the millennial set, while Firehouse Brewing Company is serving up a fine assortment of brews that would be equally at home in a larger metropolis like Denver or St. Louis.

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Where to Stay in Black Hills

With all this open space, you’re gonna want your own room to roam. So instead of packing into a hotel, score your own rental accommodations at Creekside Home about 10 miles from town. With a large wooden deck overlooking a peaceful babbling creek and plenty of space for families, the 24,000-square-foot home offers three bedrooms and two bathrooms over two floors, with its own weight room and plenty of open space. Hike along the property, read a book under the gazebo overlooking the creek, and consider yourself lucky to be alive.

The Creek-side Home In The Black Hills

Rapid City
9.6 Excellent (161 reviews)