Flyover country it is not. The Midwest offers a variety of landscapes, ripe for exploration with a classic road trip. From rolling vineyards to lush river valleys, high limestone bluffs to some pretty great lakes, this region of the United States is often overlooked. It’s time to change that, so cue up a playlist, pack your favorite snacks, and hit the road on one of these top Midwest road trips, which are sure to highlight the best of America’s pulsing, vibrant heartland.
Wisconsin's Great River Road
Start: Prescott, WI
End: Kieler, WI
Length: 234 miles
The picturesque city of Prescott, situated where the St. Croix River meets the Mississippi River, makes for a great jumping-off point for this road trip. Start at the Great River Road Visitor & Learning Center and drive south along Wisconsin’s 250-mile stretch of the National Scenic Byway, which hugs the Mississippi’s curves and bluffs. In addition to pretty views, this area of Wisconsin offers unexpected culinary delights in tiny river towns. Bay City’s Chef Shack is worth a stop for its lovely back patio and two James Beard Award-nominated chefs at the helm.
Pepin, Wisconsin, located on the widest natural part of the river — the aptly named Lake Pepin — also deserves some attention. There, check out the Harbor View Cafe, which has been impressing visitors since 1980. Meanwhile, fans of the “Little House on the Prairie” books can visit the birthplace of writer Laura Ingalls Wilder, a roughly 10-minute journey inland from Lake Pepin. Continue along the beautiful highway past La Crosse, Wisconsin, then, consider cutting inward to Viroqua, Wisconsin, via State Highway 14. The rolling hills and pastureland of Vernon County are home to the highest concentration of organic farms in the state. Visit the Driftless Cafe, home to another James Beard Award nominee, for the best farm-to-table fare in the region.
Wine lovers should consider hitting some stops on the Great River Road Wine Trail, especially Danzinger Vineyards on the bluff in Alma. Those who prefer a hoppy beverage can stop at the Potosi Brewery near the end of this road trip. The Great River Road stretches beyond Wisconsin, but Kieler is the last stop before it crosses the border and continues on to Iowa’s pretty river city of Dubuque.
With a total driving time just under five hours, this trip could be done in a day, but most of the attractions are right at the start. A nice way to break it up into a two-day trip is with an overnight stay near the vineyards.
Indiana's Natural Wonders and Small Towns
Start: Indiana Dunes National Park, IN
End: Bloomington, IN
Length: 288 miles
Begin at the 15,000-acre Indiana Dunes National Park in northwestern Indiana. Situated on Lake Michigan’s beautiful southern shore, this area is perfect for birding, beach time, and other activities in nature. From there, drive to the small lake town of Winona Lake to browse the little shops along the waterfront. For an upscale bite, stop into Cerulean, and for more laidback fare, consider the BoatHouse Restaurant. Spend the night two and a half hours south at The Alexander in downtown Indianapolis, both the capital and largest city in the state.
Explore the city using the Canal Walk, visit the acclaimed Indianapolis Children’s Museum, scope out some street art, and enjoy a meal at St. Elmo Steak House. For an extra dose of exercise in the city, check out the Monon Rail Trail, a former rail line that stretches from Indy to the northern suburbs. After your time in the capital city, head south to Bloomington, home to Indiana University. This college town offers both a picturesque campus and a walkable downtown area. Continue on to Brown County State Park, the largest in Indiana, which is open for picnicking, hiking, horseback riding, and more.
Read more Lady Bird Johnson Grove Nature Trail
You'll be on the road for at least five hours on this trip. Considering that you will want a day or two for exploring all Indianapolis has to offer, the trip should be broken up into two legs at least.
Nebraska's Sandhill Journey
Start: Grand Island, NE
End: Bayard, NE
Length: 335 miles
Begin your journey in Grand Island, an area that truly shines in the spring with the world’s largest sandhill crane migration. From there, follow State Highway 2 to Broken Bow, where you can access information on the route at the Sandhills Journey Scenic Byway Visitor Center. Thirsty travelers can imbibe at Kinkaider Brewing Company, which offers a taproom and restaurant in the gateway to the Sandhills.
After indulging responsibly (nominate a designated driver in advance), continue on Highway 2 until you reach the town of Anselmo, where you’ll take a slight detour to Victoria Springs State Recreation Area, an oasis known for its healing mineral waters. Here, road-trippers can enjoy activities like paddleboarding, fishing, and picnicking at one of Nebraska’s oldest state recreation areas. In the summer season, the park’s log cabins make for a fun overnight option and can be reserved up to a year in advance. Pro tip: If you opt for an overnight, be sure to check out the stars without the usual light pollution interference.
End at perhaps the quirkiest attraction on this list, Carhenge, a replica of England’s Stonehenge crafted with old cars. Bonus: For those who want a taste of the Oregon Trail, consider a journey to the Chimney Rock National Historic Site in Bayard, less than an hour beyond Alliance.
You'll be on the road for about six hours with this itinerary, with the longest leg being between Anselmo and Alliance. If you take your time at the Sandhills or Victoria Springs, you can break this trip up over two, three, or four days.
Route 66's First Leg
Start: Chicago, IL
End: St. Louis, MO
Length: 315 miles
Route 66, which runs from Chicago, Illinois, to the Santa Monica Pier in Los Angeles, is a classic, and you can explore a portion of it in the Midwest. Start in the Windy City, after enjoying some of its famous deep-dish pizza. Additionally, you may want to stop for a photo op at the corner of Michigan and Adams, where the historic “Begin Route 66” sign stands. Then, head to nearby Wilmington to see one of the famed Muffler Men statues, the Gemini Giant, near the charming Launching Pad restaurant. From Wilmington, it’s a roughly two-hour drive to the Illinois capitol of Springfield, where history buffs will want to check out the numerous Abraham Lincoln sites. Highlights include the Lincoln Home, his Presidential Library and Museum, and the Lincoln Tomb.
Next, journey onward to St. Louis. Travelers can stretch their legs at the famous Chain of Rocks Bridge, which has since been turned into part of the Route 66 Bikeway. The bridge is even on the National Register of Historic Places. End your intro to Route 66 in luxe fashion with an overnight stay at the surprisingly affordable Four Seasons Hotel St. Louis, a short walk from Gateway Arch National Park. The property boasts a tasty eatery with a James Beard Award-winning chef as well as a full spa. Plus, it’s close to another must-visit St. Louis attraction for kids: the interactive City Museum.
Getting from Chicago to St. Louis takes approximately five hours. History buffs may want to spend the night in Springfield to make the most of the Lincoln-related attractions, but an afternoon may be sufficient to pay your respects to the late American president.
Minnesota's North Shore
Start: Duluth, MN
End: Grand Portage, MN
Length: 112 miles
This drive follows the scenic State Highway 61 along Lake Superior’s stunning, rocky shores. Part of the Arrowhead Region in northeast Minnesota, this drive belongs on any U.S. road trip bucket list. Begin in Duluth, Minnesota, which is famous for its breweries and native Bob Dylan, who was born in the city and raised in nearby Hibbing. Walk along Bob Dylan Way for a glimpse of the folk music legend and his childhood home. Consider sipping some artisan spirits at Vikre Distillery, which offers views of the famed Aerial Lift Bridge. To pay homage to the region’s Scandinavian roots, sample Vikre’s aquavit, also known as “Norwegian Everclear.”
For an overnight stay, consider checking vacation rental options in pretty Two Harbors; this town is an excellent base for exploring Gooseberry Falls, Minnesota’s most visited state park, and Split Rock Lighthouse, one of the most photographed spots in the state. Road-trippers should also plan to fill up on pizza at longtime favorite Sven and Ole’s in Grand Marais.
The whole drive will only take you about two hours if you go straight through, so you could do it as a busy day trip from Duluth, or take your time to enjoy the lake over the course of two or three days. From roughly May to October, intrepid explorers can consider an extension to Michigan’s remote and gorgeous Isle Royale National Park. Daily ferry transport is available from Grand Portage, Minnesota, the scenic end point of this North Shore excursion. The ferry takes about two hours, and if you want to spend the night you can find a room or go camping in Rock Harbor or Windigo.
South Dakota's Monuments and Scenery
Start: Sioux Falls, SD
End: Mount Rushmore, SD
Length: 513 miles
Begin in the state’s largest city, Sioux Falls, with a walk around pretty Falls Park. Then, drive to nearby Mitchell, just over an hour away, to visit the quirky and fun attraction that is The World’s Only Corn Palace. You can stop for the views as you pass by Badlands National Park, or continue on through Rapid City — where you can visit the state’s oldest-operating brewery, Firehouse Brewing Company, for a cold beverage — to the ever-enchanting kitsch of historic Deadwood. Even though it’s super-touristy, everyone should visit at least once.
Additionally, visitors can see some gorgeous waterfalls, hiking paths, and rock ridges in Spearfish Canyon, which is actually more ancient than the better-known Grand Canyon. Also, try the well-awarded brews at Spearfish Brewing Company. For those who want an additional taste of the winding road, consider some time on the Spearfish Canyon Scenic Byway. From there, go south to the Crazy Horse Memorial in the town of Crazy Horse, which is the biggest mountain carving on Earth and has been under construction for decades.
If the carved faces of Mount Rushmore, South Dakota’s most-visited attraction, are your goal, be sure to take your time when driving on a part of the lovely Peter Norbeck National Scenic Byway. Outdoorsy types may also enjoy a visit to Custer State Park, the largest in the state.
With over nine hours of driving time to complete this trip from Sioux Falls, you will need a few days on the road. Rapid City and Deadwood are good options for overnight stays — especially if your trips are Rushmore-oriented — unless you prefer to do some camping in the parks.
Start: Sault Sainte Marie, MI
End: Leland, MI
Length: 222 miles
Begin in the small town of Sault Ste. Marie, perched between Lake Superior and Lake Huron and adjacent to its Canadian sister city of the same name. Be sure to sample the beer at Soo Brewing Company, shortened to Soo Brew by locals. Also check out the “lynchpin of the Great Lakes,” the Soo Locks, except from January through March, when they are closed for repairs. Nature lovers may consider a detour, heading westward first to Michigan’s second-largest state park, Tahquamenon Falls State Park, which boasts over 50,000 acres of pristine wilderness, including one of the largest waterfalls east of the Mississippi. It will addd about 75 miles to the trip, however.
For an overnight option to break up the drive, stay at the historic Grand Hotel on carless Mackinac Island (Note: Like many of the Island’s businesses, the hotel is only open during the island’s high season between May and October). Be sure to build in time to try some of this destination’s famous fudge, too. The charming island can be accessed via ferry from Mackinaw City (Lower Peninsula) or St. Ignace (Upper Peninsula). After experiencing some of the delights of the Upper Peninsula, cross the one of the world’s longest suspension bridges, the Mackinac Bridge, to Michigan’s Lower Peninsula, which everyone calls “the mitten” for its shape. Once you cross the bridge, consider a nighttime visit to nearby Headlands International Dark Sky Park, where it’s possible to catch a glimpse of the northern lights if you get very lucky with your timing. If not, you’ll still enjoy a brilliant display of stars there.
From the preserve, it’s just a two-hour winding lakefront drive to Traverse City, known as Michigan’s foodie capital, where you should stop and eat at the French-inspired Brasserie Amie. If you have a sweet tooth, cap off your meal with a stop at the wildly popular Grand Traverse Pie Company. End your trip on the gorgeous Leelanau Peninsula, Michigan’s answer to Wisconsin’s storied Door County. Check out Leland’s Fishtown, take the ferry to the Manitou Islands (part of Sleeping Bear Dunes National Lakeshore), and imbibe at the wineries on the Leelanau Peninsula Wine Trail.
Not including times spent on ferries, the total driving time for this trip is just under five hours, but with so much to see plan to have lots of time saved for dilly-dallying. Three to five nights are ideal so you can really enjoy this itinerary that touches three out of the five Great Lakes.