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

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.

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.

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.

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.

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.

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.