Summary of Top Midwest Road Trips
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; 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, 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 — deserves 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, via State Highway 14. The rolling hills and pastureland of Vernon County are known for their high concentration of organic farms. 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; however, most of the attractions are right at the start. A nice way to break it up into a two-day journey 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, situated on Lake Michigan’s beautiful southern shore, perfect for birding, beach time, and other outdoor activities. 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, while 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 stretching 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.
You’ll be on the road for at least five hours on this trip. Considering that exploring all Indianapolis has to offer is recommended, 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 shines in the spring with the world’s largest sandhill crane migration. From there, follow State Highway 2 to Broken Bow, where information on the route can be accessed at the Sandhills Journey Scenic Byway Visitor Center. Thirsty travelers can enjoy beverages at Kinkaider Brewing Company, which offers a taproom and restaurant in the gateway to the Sandhills.
After indulging responsibly, continue on Highway 2 until you reach the town of Anselmo, where you’ll take a slight detour to Victoria Springs State Recreation Area, known for its healing mineral waters. Here, road-trippers can enjoy paddleboarding, fishing, and picnicking at one of Nebraska’s oldest state recreation areas. The park’s log cabins are available for a fun overnight option in the summer season, which 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, Carhenge, a replica of England’s Stonehenge crafted with old cars. 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.
This itinerary will take you about six hours on the road, with the longest leg being between Anselmo and Alliance. If you take your time at the Sandhills or Victoria Springs, you can stretch this trip 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 road trip, 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. You may want to stop for a photo op at the corner of Michigan and Adams, where the historic “Begin Route 66” sign stands. Next, 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 Springfield, where history buffs will want to check out numerous Abraham Lincoln sites, including the Lincoln Home and the Presidential Library and Museum.
Next, journey onward to St. Louis, where travelers can stretch their legs at the famous Chain of Rocks Bridge, now part of the Route 66 Bikeway. The bridge is listed on the National Register of Historic Places. End your introduction to Route 66 with an overnight stay at the surprisingly affordable Four Seasons Hotel St. Louis, located a short walk from Gateway Arch National Park. This hotel features a tasty eatery with a James Beard Award-winning chef, as well as a full spa. Additionally, it’s close to the City Museum, an interactive attraction that is perfect for children.
Traveling from Chicago to St. Louis takes approximately five hours. History buffs may want to spend the night in Springfield to make the most of Lincoln-related attractions; however, 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. Located in the Arrowhead Region of northeast Minnesota, this drive is a must-have on any U.S. road trip bucket list. Begin in Duluth, known for its breweries and as the birthplace of Bob Dylan. Walk along Bob Dylan Way for a glimpse of the folk music legend’s childhood home. Consider sampling artisan spirits at Vikre Distillery, which offers views of Aerial Lift Bridge. To pay homage to the region’s Scandinavian roots, you can sample Vikre’s aquavit, also known as “Norwegian Everclear.”
If you’re looking for an overnight stay, consider vacation rentals 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 state’s most photographed locations. Road-trippers should also plan to fill up on pizza at the longtime favorite Sven and Ole’s in Grand Marais.
The whole drive will take about two hours if going straight through, making it suitable for a busy day trip from Duluth; however, taking your time to enjoy the lake over the course of two or three days is also an option. From roughly May to October, adventurers can consider extending their trip to Michigan’s remote Isle Royale National Park, accessible by a daily ferry from Grand Portage, Minnesota, taking about two hours.
South Dakota’s Monuments and Scenery
Start: Sioux Falls, SD
End: Mount Rushmore, SD
Length: 513 miles
Begin in Sioux Falls, the state’s largest city, with a walk around picturesque Falls Park. Next, drive to Mitchell to visit The World’s Only Corn Palace. You can stop for the views as you pass Badlands National Park, or continue through Rapid City, home to the state’s oldest-operating brewery, Firehouse Brewing Company. Enjoy the charm of historic Deadwood.
Visitors can marvel at beautiful waterfalls, hiking paths, and ancient rock ridges in Spearfish Canyon, which is older than the Grand Canyon. Be sure to try the well-awarded brews at Spearfish Brewing Company. Those craving extra adventure may want to follow the Spearfish Canyon Scenic Byway. Lastly, make your way south to the Crazy Horse Memorial, the biggest mountain carving on Earth, currently under construction.
For visitors aiming to see the carved faces of Mount Rushmore, South Dakota’s most-visited attraction, take your time driving on the lovely Peter Norbeck National Scenic Byway. Outdoor enthusiasts will also enjoy visiting Custer State Park, the largest in the state.
With over nine hours of driving time from Sioux Falls, you’ll need a few days on the road. Rapid City and Deadwood are ideal overnight stays, especially if your visits are Rushmore-oriented or if you prefer camping in the parks.
Michigan’s Peninsula
Start: Sault Sainte Marie, MI
End: Leland, MI
Length: 222 miles
Begin in Sault Ste. Marie, perched between Lake Superior and Lake Huron. Sample the beer at Soo Brewing Company, shortened to Soo Brew by locals. Check out the Soo Locks, but note they are closed for repairs between January and March. Nature lovers may consider a detour to Tahquamenon Falls State Park, adding approximately 75 miles to the trip.
For an overnight selection, consider staying at the historic Grand Hotel on carless Mackinac Island (Note: The hotel operates only during the high tourist season between May and October). Be sure to save time for the destination’s famous fudge. The island can be accessed by ferry from Mackinaw City or St. Ignace. After exploring the Upper Peninsula, cross the Mackinac Bridge to Michigan’s Lower Peninsula, or “the mitten” as locals call it. To catch a glimpse of the northern lights, consider a nighttime visit to Headlands International Dark Sky Park.
The drive to Traverse City is two hours, known as Michigan’s foodie capital; be sure to eat at the French-inspired Brasserie Amie. History buffs should save room for dessert at the Grand Traverse Pie Company. Lastly, end your journey on the stunning Leelanau Peninsula, fondly known as Wisconsin’s Door County. Visit Leland’s Fishtown, take the ferry to the Manitou Islands (part of Sleeping Bear Dunes National Lakeshore), and enjoy the wineries on the Leelanau Peninsula Wine Trail.
The total driving time for this trip is just under five hours, but with so much to see, plan ample time to explore. A length between three to five nights is ideal to fully enjoy this itinerary, showcasing three of the five Great Lakes.
