The Best Road Trips in America: Underrated Midwest Cities

  • The Best Road Trips in America: Underrated Midwest Cities

    You already know Detroit trends toward cool and Chicago’s a Midwestern hub for world-class culture. But what about those “second cities”—places like Milwaukee, Indy, St. Louis, and Louisville?


  • Road Trip Itinerary: The Best Cities of the Midwest

    Go where fewer of your friends have gone. You can also easily swing through smaller towns like Madison, Iowa City, Grand Rapids, and Fort Wayne for college-town chill and big-city fun on a smaller scale. For a 10-day road trip that folds in regional artisan foods and craft beer; lesser-known art museums and cultural institutions; natural spaces like parks, lakes and rivers; and quaint Main Streets for eclectic shopping. Get your engines started like an Indy 500 racecar. It’s time to see what many dub “flyover country” with new eyes and a fresh perspective to stop those naysayers in their haughty tracks.

    At a Glance:

    Starting Location: Indianapolis, Indiana

    Ending Location: Indianapolis, Indiana

    Miles Traveled: 1462

    Suggested Duration: 9 nights

    States Visited: Indiana, Iowa, Kentucky, Michigan, Missouri, Ohio, and Wisconsin

    Jesse Wong

  • Stop 1: Indianapolis to Louisville, Kentucky

    Stop Locations: Indianapolis, IN to Louisville, KY

    Total Travel Time: 1 hour 45 minutes

    Total Miles: 115 miles

    Recommended Route: It’s a straight shot down I-65 S. Between the two cities are only rural areas and small towns. South of Underwood, Indiana, you’ll pass through a portion of Clark State Forest.

    Along the Way:

    Eat & Drink: Zaharakos, in Columbus, Indiana, has been in business since around 1900 and continues to be a popular ice-cream shop for locals today. Before or after ordering, check out the second-floor museum’s antique soda-fountain finds, dating back to the 1800s.

    Town: Love architecture? Columbus, Indiana, is home to a surprising number of modernist works, including many by Eero Saarinen. Here’s a handy guide about where to find them.

    Upon Arrival:

    Do: At night, walk over the Big Four Bridge: this converted railroad bridge is pedestrian-only and lit up at night. Even if you’re not a sports fan, diving into the history of baseball-bat manufacturing (made since 1884 at Louisville Slugger Museum & Factory) or learning about the late boxer Muhammad Ali (Muhammad Ali Center) is captivating.

    Eat & Drink: Local chef (and former Top Chef contestant) Edward Lee has morphed into a celeb in recent years but you may be lucky to snag a reservation at 610 Magnolia Street, MilkWood or Whiskey Dry.

    Stay: The 91-room 21C Museum Hotel —tucked into 19th -century warehouses—is part art museum, part sweet stay, with sculptures and installations everywhere you look. Keep an eye out for a bronzed Michelangelo’s “David” replica: you can’t miss it.

    Breakfast: Tres Leches Pancakes and Dulce de Leche French Toast. Need we say more? Con Huevos has two Louisville locations.


  • Stop 2: Louisville to St. Louis, Missouri

    Stop Locations: Louisville, KY to St. Louis, MO

    Total Travel Time: 3 hours 50 minutes

    Total Miles: 260 miles

    Recommended Route: I-64 W takes you directly west to St. Louis. You’ll pass through Evansville, Indiana, a college town (home to the University of Southern Indiana and University of Evansville). Don’t forget to set your clocks back an hour as St. Louis is in Central Standard Time.

    Along the Way:

    Eat & Drink: You’ll find the most variety of non-chain restaurants in Evansville, Indiana. Craving a sweet snack? Be Happy Pie Company is one option, with five-inch pies and “pie bites” more suitable for one or two people.

    Nature: The Southern section of the Hoosier National Forest overlaps with I-64 W. To reach it, exit in Saint Croix and take IN-37 S to IN-62 E for an easy one-mile hike on the Celina Interpretive Trail, departing from the Celina boat ramp and with 12 interpretive stops.

    Upon Arrival:

    Do: St. Louis’ 1,300-acre Forest Park is home to the totally free-to-enter Saint Louis Art Museum. Two other sculpture parks link nature with art (and, again, are free): Laumeier Sculpture Park and Citygarden Sculpture Park. To feel like a kid again, check out City Museum, an artful indoor reuse project that involves slides, climbing and other interactive fun for all ages in a century-old warehouse.

    Eat & Drink: Craving Italian? You’ll find toasted ravioli (breaded and deep-fried), a signature St. Louis dish, in The Hill neighborhood’s restaurants, such as Mama’s on the Hill. For a latte break, drop into Kaldi’s Coffee, adjacent to Citygarden Sculpture Park with an equally artsy interior.

    Stay: Angad Arts Hotel is the only hotel out there that will ask you what your mood is upon check-in…and then send you to a room awash in a color that matches.

    Breakfast: Don’t even think about leaving without sampling gooey butter cake. The Mud House —a Boho-chic café in the cute and historic Cherokee District—features it on their menu, along with grits and greens, biscuits and gravy, and spicy tofu scramble.

    Sean Pavone/Shutterstock

  • Stop 3: St. Louis to Iowa City, Iowa

    Stop Locations: St. Louis, MO to Iowa City, IA

    Total Travel Time: 4 hours

    Total Miles: 260 miles

    Recommended Route: US-61 N takes you directly north to Iowa. You may even find the temperature drops.

    Along the Way:

    Town: Near Hannibal, Missouri, are quite a few wineries with tasting rooms and, in recent years, breweries, too. Cave Hollow West Winery’s wines are inspired by Mark Twain’s books while Mark Twain Brewing Company, across the street from Twain’s boyhood home, is another ode to him.

    Eat & Drink: Mount Pleasant, Iowa, is a nice place to pull off for lunch, like at the rustic, roadside River Rock Café with outdoor seating and it’s along the Skunk River.

    Upon Arrival:

    Do: Not every city has a pedestrian mall like Iowa City: check out Prairie Lights Books & Cafe (fitting for this UNESCO City of Literature) and, nearby, Artifacts for unique vintage finds, from clothes to furnishings) 15­ minutes outside the city is Herbert Hoover Presidential Library and Museum, dedicated in 1962. On the University of Iowa campus is Stanley Museum of Ar t and Museum of Natural History.

    Eat & Drink: College towns are full of casual, ethnic-eating opportunities, such as Oasis Falafel or Szechuan House (its owners hail from New York City). Close out the night with a drink at The Vue Rooftop, on the 12th floor of the Hilton Garden Inn Iowa City and with an amazing view and “big city” vibe.

    Stay: The 56 ultra-mod suites at Hotel Vetro (downtown) are the perfect, pampering spot to crash after a day of go-go-go.

    Breakfast: Stick a fork into soul food infused with Midwestern ingredients at Bluebird Diner where the breakfast menu includes a The Rajun Cajun omelet and Oeufs Louis XIV (eggs scrambled with black truffles).

    Suzanne Tucker/Shutterstock

  • Stop 4: Iowa City to Madison, Wisconsin

    Stop Locations: Iowa City, IA to Madison, WI

    Total Travel Time: 3 hours

    Total Miles: 175 miles

    Recommended Route: You’ll travel along the Great River Road, a 250-mile chunk of gorgeous scenery that includes Dickeyville. Be sure to also take photos of the Mississippi River when you pass over, in Dubuque, Iowa.

    Along the Way:

    Eat & Drink: Mount Horeb’s Norwegian influence pops up in a few restaurants, including Sjolind’s Chocolate House on Main Street, which also serves pastries and sipping chocolate.

    Roadside Attraction: Dickeyville Grotto in Dickeyville, Wisconsin, lies along 61 and is like nothing you’ve ever seen. Established by a priest between 1925 and 1930, it’s a great example of the state’s Outsider art, where untrained artists used found objects (wood, rocks, shells, etc.) to create beautiful spaces.

    Detour: Mt. Vernon, Iowa, is a super-cute small town and home to Cornell College.

    Shop: The German-founded Amana colonies are a locals’ favorite day-trip destination for gift shops and also a bakery and café. Pick up a loaf of German Dill or German Black bread.

    Upon Arrival:

    Do: You didn’t come all this way to not try cheese. Fromagination is a Parisian-inspired cheese shop on Capitol Square. Stroll State Street (rubbing elbows with a growing number of chains, its remaining indie shops sell Fair Trade goods and unique finds) to the University of Wisconsin-Madison and enjoy Babcock Hall Dairy Store ice cream (crafted on campus) at Memorial Union’s Daily Scoop from its outdoor terrace hugging Lake Mendota. Check out one of the country’s few Thai pavilions at Olbrich Botanical Gardens in Monona.

    Eat & Drink: L’Etoile is a farm-to-fork, fine-dining institution (founder Odessa Piper shopped the Dane County Farmers Market across the street back in the 1970s) while its more casual sibling—Graze —is a block away.

    Stay: Graduate Madison merges preppy-chic with laid-back fun, a block off State Street and a few blocks from UW-Madison’s Memorial Union. Enjoy drinks with cheese curds on the rooftop lounge.

    Breakfast: Mickie’s Dairy Bar on Monroe Street is a classic, no-frills breakfast institution for anyone who went to UW-Madison, with omelets, shakes and root-beer floats.

    csfotoimages/iStock Editorial

  • Stop 5: Madison to Milwaukee, Wisconsin

    Stop Locations: Madison, WI to Milwaukee, WI

    Total Travel Time: 1 hour 20 minutes

    Total Miles: 79 miles

    Recommended Route: Once you’re on I-94 E, that’s literally all you have to do. Just drive the highway and notice the quaint red barns and rolling green hills. Rarely is there traffic between Madison and Milwaukee.

    Along the Way:

    Photo Op: No, that’s not a space ship: the saucer-shaped building at the Johnson Creek exit (exit #267) off I-94 is the former Gobbler supper-club restaurant. Now it’s a theater with live performances.

    Eat & Drink: Even if it’s not state-fair season, you can still snag the biggest cream puffs you’ve ever seen at the Pine Cone Travel Plaza’s bakery, also at exit #267.

    Nature: Aztalan State Park in Jefferson is on former Indian burial mounds and just a few minutes off I-94. While small in size, many have found it to be a spiritual destination.

    Upon Arrival:

    Do: With its soaring white wings over Lake Michigan, the Milwaukee Art Museum’s Santiago-Calatrava-designed Quadracci Pavilion is often linked with the city’s skyline. Rent a shared bike from Bublr and cruise up Lincoln Memorial Drive along the lake. Love water? Milwaukee Kayak Company rents out kayaks, canoes and SUPs at its Harbor District locale and provides a great way to experience downtown Milwaukee, from the Milwaukee River.

    Eat & Drink: Food halls are where it’s at, either the mostly black-owned eateries at Sherman Phoenix or the Pike-Place-like Milwaukee Public Market. Close down the night with a Pink Squirrel at a classic Milwaukee cocktail lounge, either Bryant’s or At Random. Frozen custard is a must, either at Leon’s Frozen Custard (the vintage neon sign will lure you in) or a Kopp’s location.

    Stay: Milwaukee’s called Brew City for a reason: beer barons emigrated from Germany to here. Bunk at the 90-room Brewhouse Inn & Suites, within the former Pabst Brewery complex and home to antique copper kettles once used to make beer.

    Breakfast: Since the 1970s, Beans & Barley on the East Side has managed to fuse Mexican with vegan and organic for all-day dining, along with old-fashioned pie slices and killer coffee in a sunny, high-ceilinged diner. Pick up snacks and a magazine for the ferry in the attached market.


  • Stop 6: Milwaukee to Grand Rapids, Michigan

    Stop Locations: Milwaukee, WI to Grand Rapids, MI

    Total Travel Time: 3 hours 40 minutes

    Total Miles: 128 miles

    Recommended Route: Today you’re leaving part of the drive to the Lake Express ferry captain. The high-speed car ferry departs from the Port of Milwaukee (just south of the Hoan Bridge in Bay View) and drops you off in Muskegon, Michigan. From there, it’s an easy 45-minute trip along I-96 E.

    Along the Way:

    Photo Op: Be sure to scale a flight of stairs to the ferry’s roof but bring a jacket: it’s cold and windy up there.

    Detour: Grand Haven (south on US-31 22 miles from the ferry terminal), along the Lake Michigan shoreline, is that quintessential summer-beach town with a boardwalk.

    Eat & Drink: Rebel Pies in downtown Muskegon can hook you up with a pizza (signature pies carry names like “Polynesian Farmer” and “The Jack White”) and a craft beer, thanks to its co-tenant Unruly Brewing.

    Upon Arrival:

    Do: The LEED-certified Grand Rapids Art Museum downtown is a gem with rotating exhibitions and a collection spanning Renaissance to Modern art. Stretch your legs at Frederik Meijer Botanical Gardens & Sculpture Park or learn about a past president at Gerald R. Ford Presidential Library & Museum.

    Eat & Drink: Opt for a local craft beer (Grand Rapids is nicknamed Beer City USA) with dinner at either The Green Well, a gastropub in East Hills, or Stella’s Lounge, known for its stuffed burger, beer-battered avocados and vintage arcade games; or head on over to Brewery Vivant in East Hills, within a former funeral chapel.

    Stay: The 48-room CityFlats Hotel with an eco-friendly mantra (it’s LEED-certified) is right downtown and near shops, restaurants, and the GRAM. Dine at the coffee shop or restaurant on site when hunger strikes.

    Breakfast: That Early Bird’s menu of items like breakfast nachos and curry hash–paired with a horchata latte, perhaps—are a fun switch on American-style breakfasts.

    Suzanne Tucker/Shutterstock

  • Stop 7: Grand Rapids to Detroit, Michigan

    Stop Locations: Grand Rapids, MI to Detroit, MI

    Total Travel Time: 2 hours 15 minutes

    Total Miles: 157 miles

    Recommended Route: I-96 E takes you from Grand Rapids to Detroit, curling around the State Capitol of Lansing.

    Along the Way:

    Detour: Jump off I-96 E at exit #90 to spot the Michigan Capitol Building and perhaps snap a photo from the car. Guided hour-long tours are offered between 9 a.m. and 4 p.m., Monday through Friday, and 10 a.m. and 3 p.m., Saturday.

    Eat & Drink: A tad southwest of Grand Rapids lies Moelker Orchards where a family has been growing apples, peaches, and cherries since 1907. The market sells farm-fresh produce and the bakery sweet treats, including pies and apple dumplings.

    Upon Arrival:

    Do: Motown Museum (including a recording studio, tucked into a home along West Grant Boulevard) and Arab American National Museum (nearby Dearborn is the country’s largest Arab-American population and this is the world’s first museum devoted to Arab culture) are two completely unique experiences you won’t find in other cities and help tell Detroit’s story.

    Eat & Drink: You’ve heard of Detroit-style pizza (rectangular with a thick, chewy crust). Now it’s time to try it! Any Jet’s location will do. For a more upscale experience, but with eclecticism, book a table at Grey Ghost Detroit. Don’t go to bed without slipping into a booth at the vintage-y Candy Bar, inside Siren Hotel.

    Stay: The new 106-room Siren Hotel is a delightful throw-back experience with its décor and boasts a restaurant (Karl’s) by one of the city’s most celebrated chefs, Kate Williams (of Lady of the House), who named it after her late great-great-grandparents’ eatery on the East Side of Detroit.

    Breakfast: Detroit’s West Village is home to Lisa Ludwinski’s wildly popular Sister Pie (she’s also the author of a cookbook of the same name) where breakfast as well as bakery items are available each morning.

    Ivan Cholakov/Shutterstock

  • Stop 8: Detroit to Fort Wayne, Indiana

    Stop Locations: Detroit, MI to Fort Wayne, IN

    Total Travel Time: 2 hours 30 minutes

    Total Miles: 162 miles

    Recommended Route: From Detroit, I-75 cuts through Toledo (you can cross another state off your list!) and weaves down to Fort Wayne.

    Along the Way:

    Eat & Drink: It’s rare to find a Hungarian restaurant which is why you need to pull over for lunch at Tony Packo’s Café (in Toledo since 1932), for the signature chili hot dog, chicken paprika, or an apple or cherry strudel.

    Roadside Attraction: In Defiance, Ohio, is a stack of five ‘60s-era VW Bugs at Pack Rat’s Pawn Shop, each decorated with further pizazz.

    Upon Arrival:

    Do: A new outdoor sculpture park downtown called Promenade Park is a great place to chill and people-watch, with kayak rentals, canal boats, and swings. Love street art? This handy interactive map points you to Fort Wayne’s best.

    Eat & Drink: For a town of only 267,000 residents, Fort Wayne is packed with such quality dining you may want to create a progressive meal during your short stay, ending with an Extreme Shake at Just Cream. But if you want to stay put while also tasting food from farms surrounding Fort Wayne, go to Bird & Cleaver Public House, owned by two culinary-school grads and in a two-story house with white-washed brick walls, lots of plants, and white midcentury-modern-style dining chairs.

    Stay: Until Provenance Hotels opens its Vera Bradley-themed hotel (she’s from here) later in 2020, options consist of chains, the 246-room Hilton Fort Wayne at the Grand Wayne Center is among the best, and right downtown.

    Breakfast: Duck into the tiny, 15-seat ‘50s-style Cindy’s Diner for all-day breakfast and what’s called “garbage” (hash browns, eggs, onions, cheese and ham—grilled together).


  • Stop 9: Fort Wayne to Indianapolis

    Stop Locations: Fort Wayne, IN to Indianapolis, IN

    Total Travel Time: 2 hours

    Total Miles: 126 miles

    Recommended Route:

    Along the Way:

    Upon Arrival:

    Do: Either stroll or rent a bike (from Indiana Pacers) to experience a portion (or all?) of the 8-mile-long Indianapolis Cultural Trail. Learn more about the Indy 500 at the Indianapolis Motor Speedway Hall of Fame, at the track, or browse the collection (works by Hopper, Homer, Matisse, Picasso and O’Keefe, for starters) at Indianapolis Museum of Art, on the 152-acre Newfields campus.

    Eat & Drink: As the state’s oldest bar, Slippery Noodle Inn in downtown Indy also hosts nightly blues sessions, allowing you to tick off live music and dinner (from wings to pasta, plus burgers, subs and salads) in one swoop.

    Stay: Explore the nightlife in Indiana’s largest city by booking a room downtown and near where it all happens, at The Alexander, with 209 rooms and Instagram-worthy dangling mouth-blown glass pendant lighting at Plat 99.

    Breakfast: Café Patachou’s omelets carry sassy names, like “The Hippie with a Benz,” and “broken yolks” are served on toast with a side of arugula salad. For a to-go treat, order “Compost Cookie,” inspired by Milk Bar owner Christina Tosi.

    Rudy Balasko/Shutterstock

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