9 Great Midwest Road Trips to Take in 2024

Distant view of Grand Marais Lighthouse approached by wooden walkway on Lake Superior — The gorgeous scenery on the shores of Lake Superior is punctuated by worthwhile stopping points like Grand Marais Lighthouse.

Comprising 12 states that include the Great Lakes, scenic state parks, and an array of world-class cities like Chicago, Minneapolis, and Kansas City, the Midwest is one of the most exciting road-trip regions in the United States. And while any time of year is a good season to explore America’s Heartland, summer offers some of the best adventures, thanks to prized hikes and trails, top-down temps, and beckoning beaches. From waterfalls and winding rivers to award-winning dining and drinking, drives in this region offer it all. Here are some of the best Midwest road trips to take right now.

Aerial view of large roadside produce store and about 2 dozen parked cars, surrounded by fields — Get your road-trip cherries at Friske.

Traverse City to Charlevoix, Michigan

Distance: 50 miles
Start: Traverse City, Michigan
End: Charlevoix, Michigan

Take US-31 north from Traverse City and watch the route evolve from bay views to farms, forests, and countryside. Stop at Friske Farm Market along the way for souvenir shopping and cherry picking (prime during summer months), then hit Bier, an art gallery featuring local works alongside an onsite brewery.
Situated on three lakes, Charlevoix is a must for water sports like kayaking and paddleboarding, not to mention its vibrant local arts and dining scene (read: freshly caught fish aplenty). Upon arrival, check into Hotel Earl, which was originally built in 1959 by lauded local architect Earl Young and redesigned in 2019. Come happy hour, head to Stafford’s Weathervane for epic lakefront views and fresh-catch options

When you make the trek back to Traverse City, don’t miss the chance to enjoy a burger at Oakwood Proper Burgers or dine at Farm Club, a farm, restaurant, brewery, bakery, and marketplace, where nearly everything is locally grown. The menu features updated takes on Midwestern classics, like cheese curd grits polenta, seared walleye, and beer-vinegar-pickled egg and rye.

Silhouette to two people in canoe on Elkhart Lake, with shoreline of trees in distance — Elkhart Lake offers appealing canoeing opportunities.

Chicago to Elkhart Lake, Wisconsin

Distance: 163 miles
Start: Chicago, Illinois
End: Elkhart Lake, Wisconsin

Rev your engines in Chicago and head due north, passing several of the city’s prettiest suburbs on the way. (For an early break, consider tea at Lake Forest’s legendary Deer Path Inn, set among sprawling green parks and lakefront landmarks.) An hour past Milwaukee, you’ll find Kohler, a town in Sheboygan County that’s home to Kohler Company manufacturing and the American Club Resort Hotel at Destination Kohler, a five-star resort boasting seven restaurants, two golf courses, and a state-of-the-art spa. If you’re seeking a bit of quiet seclusion, consider booking one of the property’s five cabins, which include full kitchens, firepits, and ample outdoor space.

Continue your travels by driving 20 miles northwest to Elkhart Lake, a waterfront village with serious hospitality. The Osthoff Resort is situated on more than 500 feet of pristine sandy shoreline and is a go-to for lakefront activities such as kayaking, paddleboating, and hydro-biking.

When evening rolls around, head downtown to the Paddock Club for seasonal small plates, like burrata with smashed peas and shaved asparagus or Calabrese cauliflower, followed by cocktails at the racing-themed Stop-Inn Tavern at Siebkens Resort. Rise early the next day for a hike around LaBudde Creek State Wildlife Area or a relaxing treatment at Osthoff’s Aspira Spa.

Aerial view of row of five bright blue umbrellas and white chairs on wood deck beside water at the Lake Shore Resort on Lake Michigan — The Lake Shore Resort on Lake Michigan is only three miles from downtown Saugatuck.

Indianapolis, Indiana, to Saugatuck, Michigan

Distance: 225 miles
Start: Indianapolis, Indiana
End: Saugatuck, Michigan

Indianapolis is a destination in its own right, so linger at the start and try lunch at the James Beard Award–nominated Milktooth, a modern-day diner with options like carrot cake waffles, sweet potato latkes, and hot honey chicken wings. Then hit US-31 for a few adventures—the first at Grissom Air Museum (75 miles north of Indy), which houses Cold War–era aircraft, and the next at Lake Manitou, about 30 miles north of there.

Once at the beach town of Saugatuck, check in at the Lake Shore Resort, then head to Oval Beach, considered one of the nation’s best for its low-key vibes and stellar sunsets. Saugatuck is known best for its waterfront charm, but don’t overlook its farm-to-table dining and bustling arts community. In addition to Saugatuck Center for the Arts, it’s home to the celebrated Ox-Bow School of Art and Artists’ Residency, where you can join in a workshop or shop in the gallery.

Those looking to continue a chilled-out itinerary can enjoy Wicks Park Gazebo Music in the Park before dinner at one of the town’s top restaurants; try Bowdie’s Chophouse, for wedge salads and shrimp cocktail, or Salt of the Earth in nearby Fennville, which also hosts live Americana and roots music. Come morning, buy a pick-me-up from Pennyroyal Café and Provisions, where chef Melissa Corey offers hearty fare like Johnnycakes and smoked whitefish croissant sandwiches.

Small, white light beacon at end of wooden pier, surrounded by lake — The harbor town of Grand Marais is a good place to stretch your legs.

Duluth to Grand Portage State Park, Minnesota

Distance: 150 miles
Start: Duluth, Minnesota
End: Grand Portage State Park, Minnesota

This 150-mile route departs from the increasingly cool port city of Duluth, which overlooks the pristine waters of Lake Superior and is known for its iconic Aerial Lift Bridge. At just under three hours each direction, the trip can be done as a day trip or you can linger longer to make a weekend out of it. From Duluth, hop on MN-61 north, hugging the lakeshore and stopping in charming harbor towns like Grand Marais and dramatic wilderness areas like Tettegouche State Park.

Your destination is Grand Portage State Park, right along the Canadian border. The park is home to Minnesota’s tallest waterfall, hiking trails, and wildlife like eagles, moose, and otters. It’s also the only state park in Minnesota located on tribal land, and in the welcome center, you can learn about the culture and history of the Grand Portage band of the Ojibwe. Nearby, stop into Grand Portage National Monument, a reconstructed 18th-century fur trading post with a museum about Anishinaabe culture.

Back in Duluth, unwind at Canal Park Brewing Company before checking into Enger Lofts Hotel & Marketplace, a stylish boutique hotel in a restored 1800s furniture warehouse. At mealtime, consider At Sara’s Table Chester Creek Cafe, where comfort food gets a modern makeover with dishes like duck pastrami salad or seared smoked provolone. For something more old-school, try the 110-year-old Pickwick Restaurant & Pub, which has been named an America’s Classic by the James Beard Foundation.

A gray, three-story estate overlooking a manicured lawn and a lakefront — Lake Geneva’s Gilded Age mansions, like Stone Manor, have earned it comparisons to Newport.

Chicago to Lake Geneva, Wisconsin

Distance: 83 miles
Start: Chicago, Illinois
End: Lake Geneva, Wisconsin

For a Midwest road-trip destination that’s just a hop, skip, and a jump away from a big city, try a drive to Lake Geneva, less than 100 miles north of Chicago. Take I-94 north and stop in Kenosha, only 28 miles out from your destination, for some of the state’s most prized souvenirs: cheese curds and a six-pack from one of the city’s many breweries, including Rustic Road Brewing Company.

Once you arrive in Lake Geneva, you’ll see why it’s been nicknamed “the Newport of the West": Its shores are lined with Gilded Age mansions where wealthy Chicago industrialists and their families used to spend summers. Check into the Grand Geneva, a 358-room resort with everything you’d need for a weekend of winding down, from golf and tennis to a full-service spa. Post up in one of its spacious villas before checking out the on-site options for dinner, such as prime cuts and seafood at Geneva ChopHouse, or venture to Hunt Club Steakhouse, the fine-dining venue at Geneva National Resort & Club, a 1,600-acre property on nearby Lake Como.

Person in red shirt standing among rocky points and deep shadows in Badlands National Park — Make a detour to Badlands National Park, where the wildlife is almost as impressive as the dramatic rock formations.

Sioux Falls to Spearfish, South Dakota

Distance: 390 miles
Start: Sioux Falls, South Dakota
End: Spearfish, South Dakota

Start this road trip in South Dakota’s largest city with such Sioux Falls staples as the SculptureWalk, the world’s largest annual exhibition of public sculptures, and stock up with macarons (in unique flavors like puppy chow and snickerdoodle) from CH Pâtisserie, which is led by Top Chef: Just Desserts winner Chris Hanmer.

Head out driving west along I-90, and in Mitchell, stop at the World’s Only Corn Palace, a site showcasing the proud harvest of South Dakota farmers. The Moorish revival building has been going strong since the 1890s, and its exterior walls are decorated with murals made of corn. About 200 miles farther on your journey, you’ll come across Badlands National Park, where you can cruise the South Unit’s perimeter for views of its iconic rock formations, while also keeping an eye open for the area’s abundant wildlife, from bison to bighorn sheep.

Back on I-90, fuel up on maple-flavored doughnuts from Wall Drug, an institution since 1931 made famous for its decades of roadside hospitality and much-advertised “free ice water.” Finish your drive in Spearfish, where you can enjoy a Pile O’Dirt Porter or 11th Hour IPA at Crow Peak Brewing before kicking back at Spearfish Canyon Lodge for a well-deserved rest.

A rocky shoreline topped by trees over a bright green waterway — Cave Point Country Park is one of the many impossibly scenic stretches of lakefront in Door County.

Green Bay to Door County, Wisconsin

Distance: 43 miles
Start: Green Bay, Wisconsin
End: Door County, Wisconsin

Situated on a peninsula between Green Bay and Lake Michigan, Door County has become a Midwesterner’s must-see for its sprawling shoreline, scenic state parks (Peninsula State Park, Newport State Park), and burgeoning food and drink scene. From Green Bay, hop on WI-57 north for lakefront views, then meander on country roads with appealing food and farm stops like Renard’s Cheese, which uses milk from small family dairy farms in Door and Kewaunee counties.

In the town of Ephraim, stay overnight at the Hillside Waterfront Hotel, where five suites and two cottages await, along with the longest porch in the county (lemonade, anyone?). Come morning, take the ferry to Washington Island to explore myriad treasures, including Schoolhouse Beach and Fragrant Isle, a 30,000-plant lavender farm with a French-inspired café.

A modern church building with a very tall spire — Among Columbus, Indiana’s most impressive modern landmarks is the North Christian Church, designed by Eero Saarinen.

Indianapolis to New Harmony, Indiana

Distance: 215 miles
Start: Indianapolis, Indianapolis
End: New Harmony, Indianapolis

Did you know that Indiana has some of the most distinctive and underrated modern architecture in the United States? Begin your journey in Indianapolis and drive south along I-65 for about 50 minutes, until you reach the town of Columbus.

Beginning in the 1950s, businessman J. Irwin Miller offered to pay the architect fees for public buildings around town. The patronage led to buildings by legends like Eliel (father) and Eero (son) Saarinen, I.M. Pei, Richard Meier, and César Pelli, earning the town the nickname “Athens on the Prairie.” Today, seven of those buildings are designated National Historic Landmarks, and the city offers a two-hour guided shuttle tour of some of the highlights. Among the landmark buildings is Miller’s own 1953 midcentury-modern residence, which features architecture by Eero Saarinen, interiors by Alexander Girard, and landscape design by Dan Kiley.

Continue driving southwest along I-69 toward New Harmony, a small town that was home to two utopian communities between 1814 and 1927; they left behind a number of 19th-century vernacular structures that, lovingly preserved, now form the New Harmony Historic District. But New Harmony isn’t stuck in the past: After marrying a descendant of one of the utopian leaders and town founders, oil heiress Jane Blaffer Owen commissioned a slew of architecture and public art projects, including the Athenaeum by Pritzker Prize–winner Richard Meier and Philip Johnson’s Roofless Church.

Exterior of modern geometic Rock & Roll Hall of Fame designed by I. M. Pei, next to water — Cleveland’s Rock & Roll Hall of Fame, designed by I. M. Pei, makes for a fine first stop on this music-themed itinerary.

Cleveland to Chicago

Distance: 450 miles
Start: Cleveland, Ohio
Finish: Chicago, Illinois

The shores of the Great Lakes and the Rust Belt cities along them have been the site of some major musical innovation. Begin this music-themed road trip in Cleveland, the home of the Rock & Roll Hall of Fame, which has a new exhibit honoring 2023 inductees like Missy Elliott, Willie Nelson, Chaka Khan, and Rage Against the Machine. If you’ve ever wondered how the city earned the honor of hosting the I.M. Pei–designed museum, it’s because of DJ Alan Freed, who promoted the new genre and broke down racial barriers in music in the 1950s. Honor his legacy with a visit to his jukebox-shaped grave in Lake View Cemetery.

Drive westward along I-90, cutting north at Toledo toward Detroit, where the Motown Museum is set to undergo a multi-million-dollar renovation and expansion. The museum incorporates Hitsville U.S.A., the record label’s first headquarters, in a white house on West Grand Boulevard that founder Berry Gordy bought in 1959. Enjoy a meal at the Black-owned Waffle Cafe at 18685 Livernois Avenue and see the Motown mural on its exterior wall by artist Fel’le, featuring the likenesses of Smokey Robinson, the Temptations, the Supremes, and others.

Continue westward through Michigan, and blow into the Windy City. Chicago is associated with so many forms of music, including blues, gospel, and modern jazz, but Gen X-ers and elder Millennials will love it for its contribution to the indie rock scene of the past three decades. See who’s playing at the Empty Bottle, Lincoln Hall, Riviera Theatre, or the Metro. Or for something a little more classic, end your night at the Green Mill Cocktail Lounge, a bebop and free jazz club that’s been going so long that Al Capone used to be a regular.

While not Chicago’s most luxurious stay, Hotel Versey is steeped in rock history; it used to be nicknamed the Rock and Roll Days Inn and has welcomed Gregg Allman, Nirvana, Radiohead, and more. Kurt Cobain and Courtney Love dyed their hair in the bathtubs here, and Sheryl Crow rollerbladed through the lobby. (Don’t do that, it’s not allowed.)

With additional reporting by Nicholas DeRenzo. This story was originally published in 2021; it was most recently updated with new information on May 21, 2024.

Nicole Schnitzler

Nicole Schnitzler is a freelance writer who covers lifestyle and culture. She is also the founder of Doors Open Dishes, a nonprofit organization that partners with chefs to help keep the doors open to group homes and organizes workshops for those with developmental disabilities.

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