Discover the 7 best Midwest road trips in USA one can take

Great open stretches of American heartland lend themselves entirely to road travel, backdropped to perfection by rolling hills, vast lakes and river valleys, to make an IMAX theatre out of your Prius windscreen. Regardless of how stylish your rental is, you’re bound to feel just cool enough burning tarmac with the volume up, the windows down and the expansive American Midwest laid out in front of you. Discover where best to start and stop with our top 7 Midwest road trip ideas below.

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Nebraska | Photo: Brandon Mowinke

1. Chicago to St. Louis (Route 66)

One of the most famous roads linking the Blues Brothers to Hollywood is of course Route 66, which starts in Chicago, Illinois and runs 4,000 kilometres all the way to Santa Monica Pier in Los Angeles. For an easier trip, we’ll venture as far as St Louis, Missouri, wending our way through Illinois’ most photogenic bits, finding rest in Joliet, Springfield and Collinsville to cover 4-5 days. Before setting out, the Windy City is sure to hold your interest for a few days more, by way of deep dish pizza and Abraham Lincoln factoids as well as photo opportunities on Lake Shore Drive, where the route originally began. Most people today start at Adams Street and Michigan Avenue, convening with other road trip enthusiasts and motorheads before running the very route that represents the hopes and dreams of a nation, from back amidst the Great Depression, all the way to the vagabonding 70s and beyond.

Little over an hour south of Chicago, Joliet marks Illinois’ Heritage Corridor with its blend of old and new upon an ex-industrial enclave. Its race track and theatre are two of the biggest lures, though Joliet Prison is also one for movie buffs, one of the filming locations for the Blues Brothers (1980). Another hour from Joliet takes us through Pontiac, the state’s unofficial ‘Route 66 headquarters’. As well as a charming town square and historic main street, you’ll also find museums, murals and swinging bridges to keep you amused. From Pontiac, we skirt through Wilmington with all its Muffler Man attractions and continue for two hours into Springfield, the state capital and home of Abraham Lincoln. A popular school field trip destination, Springfield knows just how to dress its history, featuring costumed characters and re-enactments of Lincoln’s life, particularly in Summer when the whole town regresses back to the 19th century. Our last stop before crossing into Missouri puts Mother Nature back on our radar, at the confluence of three great waterways where Mother Road meets the Great River Road to outstanding effect. Pause in either Collinsville or Alton for lunch, enjoying the scenery from the roadside before crossing the border into St Louis to cap off your trip with a visit to the Chain of Rocks Bridge, now a part of the Route 66 Bikeway.

St. Louis | Photo: Brittney Butler

2. Duluth to Grand Portage (Minnesota’s North Shore)

The next stretch of road painting the Midwest in gorgeous colours is the 240-kilometre State Highway 61 which runs along the rugged shores of Lake Superior, from Duluth, northeast Minnesota, to Grand Portage at the Canadian border. Besides the eastward view over the great lake, the tour gives us many attractions to pore over. In Duluth the focus is shared by both Bob Dylan and craft beer, two homegrown favourites best acknowledged on a walk along the Bob Dylan Way followed by a Scandinavian-themed tasting session at Vikre Distillery in view of the famed Aerial Lift Bridge. While in the neighbourhood, don’t miss out on Gooseberry Falls, Minnesota’s most visited state park, as well as Split Rock Lighthouse, an equally worthy photography spot.

Once out of Duluth, there are also unlimited treasures across the region. Drive towards Palisade Head cliff which towers over proceedings about one hour north, followed by a detour along Gunflint Trail National Scenic Byway, through the Superior National Forest which hides a number of campgrounds and smaller lakes where you can canoe, BBQ and lounge around for however long you need. Additionally, if time allows, Tettegouche State Park near Silver Bay has its own camping charms, with more waterfalls, rock climbing and hiking opportunities just one hour from our final destination of Grand Portage. If travelling during the summer months, you can also consider extending your trip across the water to Isle Royale National Park, accessible via Grand Portage and a great way to end your scenic North Shore tour.

Photo: Arthouse Studio

Grand Portage | Photo: Vincent Ledvina

3. Milwaukee to Wisconsin Dells

To explore Wisconsin in all its magnitude, one way is to go by car from Milwaukee to Wisconsin Dells by way of Green Bay. The city of Milwaukee is a fabulous place to start, not least because of its world-class breweries and haunted concert venues. A combination of foodie treats and quirky attractions, Milwaukee is sure to charm you from downtown’s Pfister Hotel right through to its historic third ward. If leaving Milwaukee on two wheels, don’t miss the Harley Davidson Museum for a splash of engine envy. Heading north from Milwaukee, we travel along the Michigan River and through cute towns like Port Washington before reaching Green Bay. While the smaller towns each hold their unique treasures, Door County’s Green Bay wins out for its closeness to Heritage Hill State Park where on football match days the Green Bay Packers fanbase goes wild.

From Green Bay, we make a sharp turn southwest toward Wisconsin Dells, a key stopping point for waterpark lovers. Besides getting wet-n-wild, the Dells offers a bunch more laid-back amusements, including hiking, duck boating and shopping, plus an optional stay at a romantic lakeside cabin. Between the Dells and final stop Madison there are a host of places to consider, many of them lakeside and every one a winner. Devil’s Lake State Park links to Mirror Lake State Park where hiking and kayaking are the prime activities, while the International Crane Foundation allows visitors to see the region’s conservation efforts and Spring Green’s House on the Rock throws a labyrinthine interactive museum into the mix. Once in Madison proper, get to grips with the lakefront layout on an afternoon walk along the Capital City State Trail, buying local at Eugster’s Farm Market just south of the city.

Wisconsin Dells | Photo: Ethan Walsweer

Photo: Ethan Walsweer

4. South Dakota

An introduction to South Dakota starts and possibly ends in Sioux Falls, the state’s largest city and home to laidback midwestern treats such as Falls Park, not far from a vast number of other wilderness attractions. To see them in order, we drive one hour to Mitchell to see ‘The World’s Only Corn Palace’ for ourselves before embarking on the four-hour drive to Crazy Horse Memorial, a more impressive mountain carving than the name might suggest. From here, it’s a short trip to uncover South Dakota’s more wild attractions, with Custer State Park and Badlands National Park earning attention despite the lure of Mount Rushmore along the Peter Norbeck National Scenic Byway.

With so much to see in the region, some travellers stick just to the Black Hills region, starting in Rapid City for live music and culture quenched by the state’s oldest brewery, before hitting Badlands, the Wall Drug oasis and Wind Cave National Park. Hot Springs is the place to rest, ostensibly for its hot springs but also for its hiking, cave tours and Mammoth history. Mount Rushmore can come after resting in Keystone a few days, the journey interlaced with drives along some of the state’s best roads including Iron Mountain Road, the Needles Highway and the Custer Wildlife Loop Road. For added interest, the Cathedral Spires Trail is one for hikers, while Sylvan Lake is another blissful rest stop. Then, if more driving is appealing, find the state’s own version of the Grand Canyon up on the northern edge of the Black Hills at Spearfish Canyon Scenic Byway.

Badlands National Park | Photo: Matan Levanon

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The Kinkaider Brewing Company can keep you in hops in the Sandhills region, though Anselmo town and its nearby Victoria Springs Recreation Area can provide much-needed healing via its mineral springs

5. Sandhills, Nebraska (Grand Island to Alliance)

For more bold and beautiful byways, Nebraska is another of the top choices for road trips in the Midwest. We begin our trip in Grand Island in spring to see the world’s biggest sandhill crane migration before setting forth on State Highway 2 to Broken Bow as part of the Sandhills Journey Scenic Byway. To learn more of Nebraska’s pioneering history, try Grand Island’s Stuhr Museum of the Prairie Pioneer or simply wonder the small-town gem of Broken Bow which is home to the Custer County Historical Society Museum.

The Kinkaider Brewing Company can keep you in hops in the Sandhills region, though Anselmo town and its nearby Victoria Springs Recreation Area can provide much-needed healing via its mineral springs. Once you arrive, try paddle boarding, fishing and picnicking within the state’s oldest recreation area, booking well in advance if you fancy staying at one of the park’s log cabins to view the stars in the pitch-black night sky. After all the natural wonder, Carhenge in the High Plains keeps it fresh with its motorised version of England’s Stonehenge, but this can easily be overlooked in favour of wilderness attractions such as the 92,000-acre Nebraska National Forest, where you can camp out or base yourself in nearby Mullen, ‘The Biggest Little Town in Hooker County’ to better see the wonders of Middle Loup and Dismal Rivers for leisurely canoeing, tubing or tanking(!) downstream.

Photo: Silviu Zidaru

Wisconsin Dells | Photo: Ethan Walsweer

6. Great River Road, Wisconsin

Wisconsin gets a second mention in our list of best Midwest road trips for reasons about to be made clear. Though Door County gets much credit for its football and forests, it’s the stretch of road that runs along the Mississippi River that is very much worthy of the 400-kilometre petrol bill. Known as the Great River Road National Scenic Byway or simply as Highway 35, this length of road comes edged in its entirety by mesmerising views, all the way from Prescott to Potosi, through 33 small river towns on the way. Stop at any number of these towns, appreciating the artist’s galleries, wineries and historic squares, catching a boat for angling and day tours or sticking to land for hiking, biking and camping within nature preserves just outside of town.

While there is always something unique to do in each town, and more than enough cheese and wine to satisfy any evening craving, the incredible scenery from the road makes the journey the biggest pleasure, passing over bluffs and the rolling pastures of Vernon County where you’ll also find the highest number of organic farms in the state. All this open land also makes the River Road a fine place for birdwatching, bald eagles in particular, which you can track up to Pepin, the widest part of the river and birthplace of ‘Little House of the Prairie’ writer Laura Ingalls Wilder. The actual river road ends at Kieler, near river city Dubuque, though some detours to look into include the trip to La Crosse and inland to Viroqua via State Highway 14, or even the Great River Road Wine Trail which lays way to the famed Danzinger Vineyards in Alma.

Lake Michigan | Photo: Adam Bouse

7. Upper and Lower Peninsula, Michigan 

The last of our road trips in Midwest takes us from either end of Michigan, from the Indiana border all the way north until we can see Canada. Our starting point lies in New Buffalo at the southern tip of Lake Michigan near Chicago. Much different from its neighbour, thanks to its sleepy European ways, New Buffalo is a good base to rest up while exploring the nearby Warren Dunes State Park before renting the car for your epic trip north. Getting from the lower to the upper peninsula can be done via Highway 31, though breaking the journey with a spell in the big city of Grand Rapids is a good call. The next mission is to get up to Traverse City, a place known as Michigan’s foodie capital and gateway to hiking at Sleeping Bear Dunes as well as the scenic fishing villages up at Leelanau Peninsula and the Manitou Islands.

After wining it up along the Leelanau Peninsula Wine Trail, make the winding journey back around Grand Traverse Bay to eventually reach Mackinaw City, the site of the Headlands International Dark Sky Park and the world’s third-longest suspension bridge which will gladly take us over to the Upper Peninsula after an optional detour to the wonders of Ocqueoc Falls in the east. Having crossed over, Michigan’s landscapes take on new shape, dominated by 40,000-acre Tahquamenon Falls State Park. Mackinac Island fudge is one reason to board a boat from St. Ignace, staying the night at the historic Grand Hotel for that extra sweet treat. Our last day of travel in the region sees us up into Sault Ste. Marie, a small town sharing its name with a Canadian sister across the St Mary’s River, where Lake Superior views take centre stage.

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