The 8 Best Road Trips to Take in the Midwest

Hit the road and discover the Midwest! From Great Lakes and rivers to rolling hills, wide-open plains and lush forests, there’s plenty of ground to cover. Whether you’re up for a long weekend road trip or a short Sunday drive, set a course for the middle section of the United States and get out there to explore some of the most diverse scenic terrains in the country. Here are eight Midwestern journeys of varying lengths and distances worth considering.

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Illinois’s Route 66 Heritage Project

Route 66 mural

Heritage Corridor Convention and Visitors Center

Without a doubt, Route 66 holds undisputed rank as the most iconic stretch of road in the United States. Brimming with Americana culture, the stories of the Mother Road come alive via the initial leg that starts in Chicago and runs 300 miles across Illinois to St. Louis. Start the journey by snapping a selfie in front of the "Begin Route 66" sign across from the Art Institute of Chicago, then journey west to lunch in Willowbrook at Del Rhea's Chicken Basket. Next up, pay your respects to Jake and Elwood at the Joliet Correctional Center before passing through Pontiac, where you'll find the Route 66 Hall of Fame Museum. Keep your eyes peeled for quirky roadside fixtures like the oversized Muffler Men statues and smiley-face water tower in Atlanta before arriving in Springfield, the Land of Lincoln. From there, it's just a hop, skip, and a jump to charming Litchfield and the picturesque Chain of Rocks pedestrian bridge that crosses over the Mississippi River into Missouri. Feeling ambitious? You can always extend the trip and get your kicks by continuing to the route's terminus in Santa Monica, California.

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Ohio’s Hocking Hills Scenic Byway

Hocking Hills Rose Lake 

Nestled into the foothills of greater Appalachia, southeastern Ohio’s Hocking Hills region lies just 40 miles south of Columbus. A lasting product of the Ice Age, Adena mound builders and Native American tribes, this land features rolling terrain, Blackhand sandstone gorges, rock ledges and cliffs, recessed caves, and photogenic waterfalls. The 26-mile byway that runs along State Route 374 winds through a beautiful cross-section of nature to appreciate (watch out for unexpected deer crossings). Stop and stretch your legs on a handful of state park hiking trails, kayak on one of several bucolic lakes, or rent a cozy cabin and stay a few days for a closer exploration of the area. 

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Minnesota’s North Shore Scenic Byway

Duluth's Aerial Lift Bridge

Explore Minnesota 

Chart a course for Duluth, where you can embark upon a memorable 145-mile journey that skirts along the edge of Lake Superior up to Grand Portage at the Canadian border. You’ll want to take your time to take in the gorgeous North Shore views, particularly during the fall when the foliage lights up in magical seasonal hues. Photo opportunities along the byway include towering bluffs that frame rushing rivers and streams underneath, rugged hiking paths and bike trails, lighthouses, and the magnificent Lutsen Mountains ski paradise. Plan to pit stop and enjoy a breather, a self-guided waterfalls tour and a picnic lunch at Gooseberry Falls State Park.

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South Dakota’s Badlands Loop Scenic Byway

Badlands South Dakota

Travel South Dakota 

Anyone who’s ever made the patriotic pilgrimage to Mount Rushmore comes away impressed by the otherworldly Badlands geography, a transformative scope of grassy stretches and startling rock buttes, mounds, and peaks. Throughout the 39-mile SD Highway 240 journey between Wall and Cactus Flat across Badlands National Park, 16 designated overlooks provide opportunities to stop and marvel at the surreal views. If you choose to stop and hike, keep your eyes peeled for appearances by the indigenous wildlife—buffalo, prairie dogs, mule deer, and antelope, to name just a few. The Minuteman Missile Visitor Center and the Ben Reifel Visitor Center are great spots to load up on helpful maps and advice. 

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Iowa’s Covered Bridges Scenic Byway

Iowa covered bridge

Travel Iowa 

“The Bridges of Madison County” celebrates its 25th anniversary in 2020, making this year the perfect time to plan a road trip to Iowa. Spanning 82 miles through a peaceful rural farming landscape, the Covered Bridges Scenic Byway guides adventurers past a number of the sites commemorated in the film. The county’s collection of historic bridges dates back to construction between 1870 and 1884, all celebrated during an annual festival each October. For those who believe in ghosts, Roseman Bridge (featured prominently in the movie) is rumored to be haunted. Keep the cinematic theme going with a visit to Winterset, John Wayne’s birthplace anchored by a friendly town square full of mom-and-pop shops and restaurants.

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Wisconsin’s Door County Coastal Byway

Door County

Destination Door County 

With 66 miles of road to cover and discover, the Door County Byway wows with waterfront views both up and down the eastern Wisconsin peninsula. Kick off the trip in Sturgeon Bay heading north up State Highway 57 skirting Lake Michigan to Gils Rock at the tip, then looping back down south along the Niagara Escarpment bluffs of State Highway 42 on the Green Bay side to come full circle at the starting point. County parks, state parks, lighthouses, charming towns and villages all merit stopping to explore; keep your tank full and your spirits high by feasting on cherries, Door County’s signature crop, at cute local eateries and diners.

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Kansas’s Flint Hills Scenic Byway

Flint Hills, Kansas

Credit: Kansas State Tourism 

Craving wide open spaces? The Flint Hills Byway clocks in at a quick 48 miles in length, but you’ll want to allow a full day to stop and experience the historic sites, vistas, and small towns as you go. Billing itself as the gateway to the tallgrass prairie, the byway offers expansive panoramic views of the Great Plains. The Kaw, Osage, and other Native American tribes populated this land centuries ago, leaving indelible footprints and impressions that still resonate today. Starting from Council Grove, the byway follows K-177 south past the Tallgrass Prairie National Preserve and over the Cottonwood River to Cassoday.

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Michigan’s Sleeping Bear Dunes National Lakeshore

Sleeping Bear Dunes

Credit: Amy Lynch 

The route may be just 7.4 miles long, but the views of Lake Michigan you’ll discover on the Pierce Stocking Scenic Drive loop make it all worthwhile. Lush forest falls away to reveal breathtaking vantage points of the vivid blue water from way up high as you make your way along the twisting, turning tour, part of the Sleeping Bear Dunes National Park. Keep the glow going with a jaunt up M-22 through lovely Glen Arbor and Leland’s historic Fishtown village, then cross the peninsula to Sutton’s Bay and travel down the west arm of the Grand Traverse Bay coastline to Traverse City.