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7 Classic Midwest Road Trips to Drive This Year

By Nicole Schnitzler

May 28, 2021

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The scenic byway near Tettegouche State Park commands must-pull-over views.

Photo by Paul Stafford/Explore Minnesota

The scenic byway near Tettegouche State Park commands must-pull-over views.

Fill up—or charge up—for these quintessential drives.

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Comprised of 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 time 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.

Get your road trip cherries at Friske.

Traverse City to Charlevoix, MI

Distance: 50 miles

Start: Traverse City, MI

End: Charlevoix, MI

Take U.S.-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, a new property that opened in September last year. It was originally designed by locally lauded architect Earl Young. Come happy hour, head to Stafford’s Weathervane for epic lakefront views and fresh-catch options, and close out the eve with Brian’s Ice Cream Experience, known for a multitude of fun flavors (from morel mushroom to RumChata). If you do make the trek back to Traverse City, don’t miss the chance to grab a burger at Oakwood Proper or dine at Farm Club, a recently opened restaurant featuring locally grown everything.  

Elkhart Lake offers some great canoeing opportunities.

Chicago to Kohler and Elkhart Lake, WI

Distance: 163 miles

Start: Chicago, IL

End: Elkhart Lake, WI

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.

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Settle into either of the property’s newest cabins—Lake or Pond—for a particularly remote stay, thanks to a full kitchen, firepit, and ample outdoor space. Then continue your travels just 20 miles northwest to Elkhart Lake, a waterfront village with serious hospitality. The Osthoff Resort, a four-diamond property situated on more than 500 feet of pristine shoreline, is a go-to for lakefront activities.

When evening rolls around, sample contemporary American fare downtown at the Paddock Club and cocktails at Siebken’s, then rise early for a hike around LaBudde Creek State Wildlife Area. If you’re craving more downtime, visit the resort’s Aspira Spa, just footsteps from your room.

The Lake Shore Resort on Lake Michigan is just three miles from downtown Saugatuck.

Indianapolis, IN, to Saugatuck, MI

Distance: 225 miles

Start: Indianapolis, IN

End: Saugatuck, MI

Indianapolis is a destination in its own right, so linger at the start and try lunch at Milktooth, a modern-day diner with options like shrimp banh mi and pistachio waffles. Then hit U.S.-31 for a few adventures—the first at Grissom Air Museum (75 miles north of Indy), the next at Lake Manitou, about 30 miles north of there. Once at the beach town of Saugatuck, check in at the Lakeshore Resort, then head straightaway to Oval Beach, considered to be one of the nation’s best for its low-key vibes and stellar sunsets.

Saugatuck is known best for its waterfront charm, but it can’t be overlooked for 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.)

Those looking to continue a chilled-out itinerary can enjoy Music in the Park before dinner at one of the town’s top restaurants (try Bowdie’s Chophouse or Salt of the Earth in Fennville). Come morning, grab a pick-me-up from Pennyroyal Café and Provisions, where chef Melissa Corey offers hearty fare like buckwheat crepes and bacon-kale hash.

The harbor town of Grand Marais is a good place to stretch your legs.

Duluth to Grand Portage State Park, MN

Distance: 143 miles

Start: Duluth, MN

End: Grand Portage State Park, MN

When researching Midwest road trip ideas, keep this circuit in mind—at just under three hours, it can work as a day trip or overnight alike. From Duluth, hop on MN-61 north the entire way for prime Lake Superior views before coming to this state park, home to Minnesota’s tallest waterfall, hiking trails, and cultural encounters (four life-sized murals showcase the story of the Ojibwe community, who occupy the land today). The photo opps alone will be well worth the trek—along with plenty of fun stops along the way (especially in the charming harbor town of Grand Marais).

Back in Duluth, unwind at Canal Park Brewing Company before checking into the neighboring Canal Park Lodge, a waterfront favorite for its proximity to the Lakewalk. For lunch, leave it to Sara’s Table, where comfort fare classics undergo a modern-day spin (truffled French fries and vegan okonomiyaki).

Don’t fill up on road trip snacks if you’re planning on ending the trip at Geneva National.

Chicago to Lake Geneva, WI

Distance: 83 miles

Start: Chicago, IL

End: Lake Geneva, WI

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For a Midwest road trip destination that is just a hop-skip from big-city living, try a drive to Lake Geneva, less than 100 miles north of Chicago. Take I-94 north and stop in Kenosha just 28 miles out from your destination for some of the state’s most prized souvenirs—cheese curds and a six-pack of New Glarus’s Spotted Cow beer—before continuing on your way.

Once there, check into the Grand Geneva, a 355-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 onsite options for dinner (like prime cuts and seafood at Geneva ChopHouse), or venture to Hunt Club, the fine dining venue at Geneva National, a 1,600-acre property on Lake Como.

Make a detour to Badlands National Park.
Sioux Falls to Spearfish, SD

Distance: 392 miles

Start: Sioux Falls, SD

End: Spearfish, SD

Start this road trip with some Sioux Falls staples, such as the SculptureWalk and Arc of Dreams (and maybe CH Pâtisserie for a croissant, too). About a third of the way along your route you’ll hit Mitchell and the World’s Only Corn Palace, a site showcasing the proud harvest of South Dakota farmers.

About 200 miles further 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 out for the area’s abundant wildlife (from bison to bighorn sheep). Back on I-90, fuel up on maple-covered doughnuts from Wall Drug, a 1931 Wall, South Dakota, institution made famous for decades for its roadside hospitality (only adding to the sugar rush in Rapid City, thanks to a stop at Pistachio Pie Bakery). Entering Spearfish, enjoy a draft at Crow Peak Brewing before kicking back at Spearfish Canyon Lodge for a well-deserved rest.

Trixie’s is not your basic road trip food option.

Green Bay to Door County, WI

Distance: 43 miles

Start: Green Bay, WI

End: Door County, WI

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 (Renard’s Cheese and the Farm, respectively).

Continue those eats upon arrival in Ephraim with a visit to Trixie’s, a bright, bustling eatery focused on the locally sourced and seriously good (ricotta agnolotti or grilled trout with roasted turnips). Find lodging footsteps away 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.

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