May 15, 2021

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Three Midwestern Road Trips for When You’re Ready to Leave Chicago

7 min read

One of the greatest parts about living in Chicago (besides TVs in every bar and the fact that you’re never more than three blocks away from a decent hot dog stand) is that, with 200+ very distinct neighborhoods, there’s always somewhere new to explore.

But every so often, even the most die-hard Chicagoan gets the overwhelming desire to ditch the Red Line for a few days. For the next time that feeling strikes, we present the three top road trips from Chicago, ranging from a couple of hours away to a full afternoon’s drive.

A mid-century mod stay in Sawyer

Airbnb

Sawyer, Michigan (1.5-hour drive)

Filled with farm stands, antique stores, and miles of beaches, Sawyer is so cute that it just may make you want to leave your busy city life behind and move into a little house on the lake, where you spend your days writing novels and wistfully staring out across the water. But until that happens, Sawyer is the perfect destination for a quick getaway weekend.   

Pit Stop: Albanese Candy Factory, Merrillville, Indiana: Pick up some road trip snacks at this enormous candy factory (yes, a five-pound bag of candy counts as a snack) and stick around to see how they make the World’s Best Gummy Bears.

Once You’re There: The Warren Dunes State Park is one of the best beaches on Lake Michigan, whether your idea of a fun day involves hiking to the top of one of the enormous dunes or sleeping in the sand all afternoon. It does get a little busy on warm summer days, so get there early and pack a picnic so you don’t have to sneak out for lunch. (And don’t forget to have cash ready for your permit to enter the state park.)

When you’ve had your fill of the lake life, hit up some of the many antique stores — including the Sawyer Antique Mall, the Dunes Antique Center and Alchemy Antiques — that line the nearby Red Arrow Highway. Who knows, maybe you’ll find a forgotten Picasso tucked away in a corner (or, much more likely, a pile of old newspapers — but hey, the fun part is the hunt).

Plus, dubbed the “Napa Valley of the Midwest” (by us, just now), Michigan has a rapidly growing wine industry. Experience it firsthand by stopping by a few of the wineries in Union Pier. St. Julian Winery is the most-awarded winery in the state, and Round Barn Winery offers tastings from their reserve plus two sister wineries.

Where to Eat: A trip to Black Currant Bakehouse in nearby Union Pier ensures that you kick off your day with a nutrition-filled breakfast of homemade doughnuts (hey, there’s fruit in some of them). Be sure to get there early — their doughnuts sell out fast.

Greenbush Brewing has amazing beer (be sure to check out their Star Chicken Shotgun IPA), but also has a delicious menu and patio seating. Plus, you can pick up beer to-go in the annex right next door.

And what’s a trip to the beach without ice cream? Oink’s Dutch Treat (in nearby New Buffalo) not only has dozens of flavors — it’s also packed with vintage ice cream paraphernalia and pig tchotchkes.

Where to Stay: While the number of hotels in Sawyer is limited, the town is a haven of unique Airbnbs, ranging from chalets to mid-century modern to even a real llama farm (and everything in between).

Kohler-Andrae State Park, Sheboygan

Kohler-Andrae State Park, Sheboygan

Lucas Ludwig

Sheboygan, Wisconsin (2.5-hour drive):

You know what they say about Wisconsin: It’s the state of beers, bratwursts and world-renown state-of-the-art water spas. Okay, maybe that last one’s not true of the entire Badger State, but it certainly is for Sheboygan, a picturesque city — sometimes called “The Malibu of the Midwest” — that contains multitudes.

Pit Stop: Mars Cheese Castle, Kenosha, Wisconsin: We’ve never actually tested this theory, but we’re pretty sure all Illinois residents are required to stop at Mars Cheese Castle whenever they cross into Wisconsin. A castle-themed cheese superstore, Mars Cheese Castle also sells meat, mustards and everything else you could think of, plus more dairy than you’ve ever seen in your life.

Once You’re There: Sheboygan is just down the road from Destination Kohler, the famous Kohler Waters Spa (yes, Kohler like the faucet at your friend’s new swanky condo). The spa features innovative water treatments like hydrotherapy massages and “riverbaths,” plus a wide range of other services.

While you’re sporting that post-spa glow, be sure to take advantage of some of the city’s beautiful outdoor spaces. The city’s Bookworm Gardens is a botanic garden centered around the theme of children’s books. And while the garden may be a hit with kids, they also offer a wide range of magical adults-only tours and events, like Twilight Picnics (complete with cheese boards — it is still Wisconsin, after all) and Secret Garden Dinners with premier local chefs.

Sheboygan’s John Michael Kohler Arts Center (are you sensing a theme? John Michael Kohler was the wealthy founder of the Kohler Company and former mayor Sheboygan in the late 1800s) features 10 galleries, a theater, and sculpture garden. And while you’re there, you won’t want to miss the bathrooms — yes, the bathrooms. The public restrooms at the Art Center are tiny art installations themselves, with artists from around the world creating interactive pieces in the restrooms, a project that began in 1974 meant to provide artists with access to industrial technologies.

Where to Eat: Black Pig serves up comfort food with a twist, with burgers, sandwiches, pasta, platters and four (4!) different variations of mac and cheese, ranging from truffle to Braised Wagyu Beef Mac. 

We’re not going to let you go to Sheboygan — also called the Bratwurst Capital of the World (seriously) — and not get a brat. Locals love Al & Al’s Steinhaus, a German tavern serving up bratwursts and a weekly Friday Night Fish Fry, another Wisconsin tradition.    

For a quick pick-me-up during the day, head over to Field to Fork, a cute café, restaurant, and grocery store featuring locally sourced products. There, you can grab food, coffee, raw juice or a cocktail made from that same raw juice (finally, a juice cleanse we can get behind).

Where to Stay: The Blue Harbor Resort is the largest resort on Lake Michigan. And while you may or may not want to partake in the resort’s on-site waterpark, you will want to request a room with a view of Lake Michigan — it looks straight out of a postcard.

Downtown Lousville

Downtown Louisville

Karthik R

Louisville, Kentucky (5-hour drive):

Louisville is a beautiful city flowing with bourbon, horse jockeys and just enough southern flavor to really feel like you’re far from home. Plus, at just under five hours away, it’s the perfect destination for that long weekend that you were hoping to spend driving across Indiana.   

Pit Stops: Purdue, University of Neil Armstrong, West Lafayette, Indiana: Snap a picture with a statue of Neil Armstrong, check out a replica of his moon steps, and even walk through a model of the solar system; and Tiny Statue of Liberty Museum, Indianapolis, Indiana: Why bother going all the way to New York City to see one giant Statue of Liberty when you can go to Indiana to see hundreds? A quick – but unforgettable – stop.

Once You’re There: What’s a trip to Kentucky without Bourbon and Horses? The Evan Williams Bourbon Factory offers a guided tour and is located in the heart of Louisville’s historic “Whiskey Row.” From there, mosey over to Churchill Downs. Even if you’re not there during the Kentucky Derby, you can still check out live horse racing (and mint juleps) most weekends from April through September — elaborate Derby hats optional.

If you’re more of a museum-hopper than a bar-hopper, Louisville still has you covered. The Louisville Slugger Museum and Factory will be a homerun with baseball fans (sorry), and the Muhammed Ali Center celebrates the life and legacy of one of Louisville’s most famous residents.

Where to Eat: Louisville has a booming restaurant scene but your first (and second …) stop should be for barbecue. Shack in the Back BBQ may be a little out of the way, but its authentic vibe and pit-cooked meat will have you bragging to friends back in Chicago about it for years.

A favorite of locals is the world-famous Shirley Mae’s Café and Bar, where Shirley herself is making made-to-order southern food like fried chicken, ham hocks and sweet potato pie. Be sure to bring cash — they don’t accept credit cards here.

Louisville also can’t get enough of converting old buildings to incredible bars. Holy Grale Pub is located in a former church with an expansive outdoor beer garden. Garage Bar is in a converted garage and also serves up woodfire pizza. And Pin and Proof Speakeasy is a bowling alley and speakeasy, located behind a mural in the Omni Hotel.

Where to Stay: If you’ve dreamed of sleeping in a museum ever since you read From the Mixed-Up Files of Mrs. Basil E. Frankweiler in sixth-grade English class, then the 21c Museum Hotel is the place for you. Part art museum, part hotel, it’s in a prime downtown location.

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