The Best Road Trips in the Midwest

Sep 11, 2019

As nicknames go, sure, you could do worse than "Flyover country." But even if it turns out not to be unforgivably dismissive, it's still a disservice. At least to travelers, who—for lack of good intel—steer clear of the Midwest. In fact, some of the nation's best road trips happen here, traversing great plains and farmlands, skirting lakes and rivers, connecting cute towns and cool cities. So do yourself a favor and skip the flyover next time: A drive through the Heartland is infinitely more rewarding, as you'll see on any of our five favorite routes.

Mississippi River Valley 
Minneapolis, MN, to Davenport, IA. 370 miles

We love an old-school Mississippi paddlewheel cruise. But if you can spare the extra time, grab your own set of wheels and point them toward Davenport as you're leaving Minneapolis. (But only after stops for Jucy Lucys, outsized kitchen objects, urban waterfalls—and some posthumous purple rain). Soon, you'll taking in some of the river valley's most stunning scenery, especially if you stop in the small city of Red Wing, where you should climb the 340-foot-high Barn Bluff. Refuel on gravy-smothered hot pork sandwiches and down-home pies at the old-timey Whistle Stop Cafe in Frontenac, then head to Winona, home to the comically niche—and improbably A-List-y—Minnesota Marine Art Museum, where you'll find works by Georgia O’Keeffe, Mary Cassatt, Pablo Picasso, Edward Hopper and Marc Chagall, among others. Also: Emanuel Leutze’s famed Washington Crossing the Delaware crossed the Mississippi a few years ago—and wound up here.

Next up: A dip into Dubuque, home to the Smithsonian-affiliated National Mississippi River Museum & Aquarium. And if you've never seen Paddlefish, Alligator Snapping Turtles, Bufflehead Ducks and a blacksmith shop under one roof, here's your chance. Furthermore, if you've never seen a real life gristmill, let alone eaten in one, Dubuque lets you tick that box, too—at a BBQ joint that's been proclaimed worthy of its own road trip, in fact.

Round out the day with a stay in nearby Galena, IL, where almost the entire 19th-century downtown has been declared a National Historic District. In that spirit (and perhaps among spirits, if you believe in haunted hotels), stay at Main Street's DeSoto House (b. 1855), where everyone from Abraham Lincoln to Ulysses Grant precedes you on the guest registry. From there, make your way back into Iowa, where Davenport will be your final stop on the Mississippi River. If you do nothing else in town, catch a show at The River Music Experience, see an exhibit at the David Chipperfield-designed Figge Art Museum and eat a duck-centric meal with a side of Matzo Ball Soup at Duck City Bistro (a political correspondent favorite during the caucuses, and a local favorite the rest of the time).


Ohio Adventure
Columbus to Cincinnati. 220 miles

This road trip strings together two of of the Buckeye State's biggest cities with plenty of pearls in between. Kick things off in Columbus' brick-, brau-, and brät-filled German Village and neighboring brewery district, both founded by German immigrants in the 1800s. Though eating and drinking your way through the area is clearly obligatory, the other must-do is less obvious to the uninitiated: The Book Loft of German Village is as famous for its historic, labyrinthine 32 rooms as it is for their contents (pretty much every book ever, at a discount, plus a staggering collection of jigsaw puzzles).

If you happen to be in town on the first Saturday of the month, don't miss the Short North Arts District Gallery Hop (a favorite local tradition that's celebrating a 35th anniversary this year), but no matter when you're here, be sure sure to hit the neighborhood's galleries, music venues and shops. This being a road trip, of course, you wouldn't want to set off without ensuring that your tank is properly full, so stop at the iconic North Market before you leave town. Despite being a historic public market, the place is also stocked with 21st-century treats—not least, global foodie favorite Jeni's Splendid Ice Creams

Then head south to the small city of Chillicothe to see the ancient, sacred mounds at the Hopewell Culture National Historic Park and—if you're here in October—the insanely popular Sleepy Hollow Experience at the Sugarloaf Mountain Amphitheatre (summertime home to Tecumseh). 

Continue south to Portsmouth, where—in keeping with the Halloween theme—you should hit the sprawling, spare-no-tchotchke A Ghost in the Attic, even if you hit no other antique shops (a local specialty). And make sure to walk through Shawnee State Park in the forested foothills of the Appalachian Mountains.

Follow the Ohio River west to Maysville, where the Kentucky Gateway Museum Center offers a fascinating overview of the regional history—and the French Quarter Inn offers awesome views of the Ohio River views, especially from the terrace. Before you check out, explore the Floodwall Mural Project, then loop back west into Ohio, and on to Cincinnati, where you have to a) hit a local chili parlor to decide where you stand on the great Cincy chili debate; cross the OG Brooklyn Bridge; meet the only local more famous than Nick Lachey; and—as truly befits a road trip—hit the American Sign Museum.


Lake Michigan Coast 
Petoskey to Holland. 270 miles

If you like your literary ghosts a tad more modern than Ichabod Crane, you'll be extra happy to start your Michigan road trip in the Petoskey region, onetime vacation home to the Hemingways, as you'll find at the Little Traverse Historical Museum (you can even arrange a Hemingway-themed local walking tour through the museum). But Hemmy fan or not, you can't help but fall for Petoskey's Victorian charms, as you'll find on even a quick stroll through the Gaslight Shopping District. Don't leave town without completing a Petoskey Stone hunt—because elsewhere in Michigan, the state stone goes for up to $750, and involves a waitlist in some cases.

Loot duly scored, drive south along the edges of Lake Michigan’s Grand Traverse Bay until you reach the tip of the Leelanau Peninsula. Stretch your legs in the eminently hike-able Leelanau State Park, where the can't-miss is the 1858 Grand Traverse Lighthouse (note that the place turns haunted Oct. 19-27, when you can tour the spooky keeper's quarters, try your hand at pumpkin bowling and gorge on s'mores). 

Continue south along Lake Michigan to Sleeping Bear Dunes National Lakeshore, one of the best spots to turn back the clock to summer and live in denial of the season's end—at least through early fall, according to The New York Times. At the Climb up (and run down) a dune; bike, blade or walk some of the Heritage Trail; then wade (even ankle-deep) into Loon Lake. 

Next up is Traverse City, home of—among several other foodie pilgrimage sites—Grand Traverse Pie Company (order anything with Montmorency cherry filling), The Cooks' House (the Michigan Artisan Cheeses with honeycomb and preserves are a favorite) and the Traverse Wine Coast (the local riesling gets a lot of vinophile love).  And when that food coma's about to kick in, you'll want to have booked a room at the close-to-everything Park Place Hotel (also a good base for exploring the Victorian shops along Front Street).

Next, head toward Manitsee, where you'll want to take in the views of the North Pierhead Lighthouse from Fifth Avenue Beach—and of the entire region from the Arcadia Overlook—before continuing south to Muskegon for the gorgeous, trail-laced state parks (check out Pere Marquette and P. J. Hoffmaster). Last stop? Holland, a town founded by (surprise!) Dutch immigrants in the 1800s whose legacy includes a number of must-sees: DeZwaan windmill; the Dutch Galleries at the Holland Museum; and—in a global fusion twist—the Tulipanes Latino Art and Film Festival (Sept. 19-22). You might even find a pint of Double Dutch at Big Lake Brewing, but whatever's on tap when you arrive, there's no better place to toast to the end of your trip.


Illinois immersion 
Cahokia to Metropolis. 250 miles 

Though you're about 800 years too late to catch Cahokia in its prime, if you'd pulled up to this indigenous site in the mid 13th century, you would have found 20,000 or so inhabitants in an urban center bigger than London's. Now, you'll find the evocative Cahokia Mounds, which make for a fitting kickoff to a history-rich road trip along the oldest “road” there is—the Mighty Mississippi. On the journey south, you’ll pass through several stretches of protected wild areas. And while the drive gets especially lovely around Chester, natural beauty is hardly the city's only claim to fame. Welcome to the hometown of Popeye the Sailor Man, whose creator was born here—and whose legacy lives on everywhere from the Spinach Can Collectibles Popeye Museum to the Popeye Character Trail. For a different kind of road trip gold, stop at the Shawnee National Forest and make your way to the stunning sandstone formations in the Garden of the Gods.

Next stop: Cairo, where the Mississippi and Ohio Rivers meet (Mark Twain fans may remember it as the promised land for Huck Finn and Jim). If you're more of a Civil War buff, check out the rivers' confluence from Fort Defiance Park, where Ulysses S. Grant launched pivotal attacks on the Confederacy.

But there's another local hero you'll want to pay tribute to before you leave the area. Not even 50 miles to the northeast sits Metropolis, Superman's official hometown. Read the—you guessed it—Metropolis Planet to see what's on when you're in town, but at a minimum, hit the Super Museum and take a #supermanselfie at the giant statue. Just don't be disappointed if the old "up, up and away" doesn't quite get you home.


South Dakota Discovery
Sioux Falls to Crazy Horse. 410 miles

What South Dakota lacks in human inhabitants—fewer than 900,000, statewide—it makes up for with one of the biggest and baddest roadtrips in the nation. (Why yes, we are talking about the Badlands, but not quite yet.) Start in Sioux Falls, where you’ll want to see the origin of the city’s name at the stunning Falls Park, get the lay of the land at the Center for Western Studies and fortify yourself with Chislic before you head west.

First stop: Mitchell, where The World's Only Corn Palace is the legendary draw. The the temple to all things a-maize-ing (forgive us) redecorates annually with kernels of more than a dozen naturally-occurring shades, and the new murals debut at the beginning of October.

For a completely different kind of amazement, continue toward Badlands National Park, where endless pinnacles, spires and buttes punctuate the largest protected mixed grass prairie in the U.S.  Stretch your legs on the park's hiking trails, wave (from a respectful distance) at a bison or pronghorn, and stay the night nearby, because you won't want to miss the morning sun creeping across the park’s jagged peaks. (Try the historic Cedar Pass Lodge if you'll be here before it closes for the season at the end of October, after which, you can book into plenty of chain hotels).

Nearby, the Minuteman Missile National Historic Site is worth the pit stop to tour the underground bunker where Cold War “missileers” once waited for orders to launch. Continuing in a northwesterly direction, pull over at the obligatory Wall Drug Store (and whether or not you're traveling with kids, take a peek at the store's "back yard").

Finish in Rapid City—not just a base for day trips to Mount Rushmore and Crazy Horse Memorial—but a place to rub elbows with all our past presidents, pick up gorgeous Native American crafts and if you can get here by Oct. 11, experience the renowned Black Hills Powwow.

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