8 Weekend Getaways Ideas in Midwest For Your Next Trip

From car racing and city highs to relaxed lazing and historical vibes, these eight Midwest getaways embrace every wonderful part of flyover country

Growing up in the Midwest was a treat. The rumors that everyone is pretty kind are true, and the breadth of activities is mind-boggling. From my base in Chicago proper, I can be out of the city and into a forest within 20 minutes – plus, I’ve got the lake directly to the east.

The rest of the region is just as interesting. We’ve got glacial landscapes, enormous hills, caves, cliffs, and islands. Add in the history of the area—including the Oregon Trail, NASCAR, and architecture—and you can see why the experiences here are varied enough to keep me around.

From a town known for seriously fast racing to the slowed down pace of Amish country, these eight weekend getaways in the Midwest will help you embrace every aspect of what it’s like to live—and enjoy living—in flyover country.

1. Swim Through the Past Lakeside in Marquette, Michigan

One of the first things you notice when you get to the lake in Marquette, Michigan is the giant ore dock on the lake. It was built in 1911, first for hematite ore and now still used for taconite iron ore pellets.

The rest of the city is just as historical as the ore dock. Marquette was founded in 1675 and is fourth on the list of the oldest cities in Michigan. You can see that history all over town, from old buildings and restaurants to historical parks and streets.

After you’ve steeped yourself in Marquette’s past, head out into the surrounding nature. You can take a canoe or kayak, swim, or fish on any of the lakes—including the big one, Lake Superior. Plus there are about 100 miles of trail to hike or bike and about a dozen waterfalls along them.

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Where to Stay in Marquette

The Landmark Inn is one of the most historic hotels in town. Construction began in 1916, though the hotel didn’t open for guests until 1930. Several of the rooms—all furnished with antiques and old- style interiors—are named after famous people who have stayed there, like Amelia Earhart and Abbott and Costello. Every room in the hotel is unique, and they all come with the amenities you’d expect: Wi-Fi, free HBO, room service, a coffee maker, and more.

Guests have access to a fitness center that has both free weights and cardio machines. The on-site restaurant, Northland Pub, is one of the highlights of the food scene in Marquette and has even been featured in The New York Times.

When you’re not eating or sleeping, you can go on a personal tour of the hotel and its meeting rooms; be sure to check out the stunning mural on the ceiling of the Sky Room and the old-world grandeur of the Boardroom.

The Landmark Inn

Top rated
9.2 Excellent (2050 reviews)

2. Live Life in the Fast Lane in Elkhart Lake, Wisconsin

If you think the Midwest runs at a slow pace, you clearly haven’t been to Elkhart Lake, Wisconsin. There are only about 1,000 people living there, and the downtown is pretty chill—you can make some pottery at hands- on art classes, grab a bite to eat in an historic restaurant, and enjoy the vintage homes on a stroll around town. But right outside town, there’s a racetrack full of action.

In the 1950s, Elkhart Lake became known for drag races happening on public roads in the village. To get the cars to a safer spot, Road America opened in 1955. It’s a track dedicated to racing, spanning just over four miles and with 14 turns. Even NASCAR races have been held at Road America. And yes—you can drive the track yourself.

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Where to Stay in Elkhart Lake

For historic charm and a relaxing atmosphere after a day at the track, check into Siebkens Resort. It opened in 1916 and is furnished with antiques. As a guest, you’ll have access to a private beach on Elkhart Lake, plus an outdoor pool.

Siebkens has three buildings – the original two are The Elm Park Hotel, with 25 rooms and all antique décor, and The Lake Cottage, situated on a bluff above the lake with six rooms. These rooms are also furnished with antiques. The newest building at the resort is the Condominium Hotel building, with deluxe condos ranging from one to three rooms. Every condo has a veranda, a full kitchen, a fireplace, and a washer and dryer.

You can choose from four dining options: a casual restaurant, the historic main dining room, a cocktail bar, and a gelato shop.

Siebkens Resort

Elkhart Lake
9.2 Excellent (224 reviews)

3. Breathe in the Great Outdoors in Hocking Hills, Ohio

Getting outdoors is the main event in Hocking Hills, Ohio. The region has nine state parks and preserves alone, in addition to three state forests, one national forest, and a plethora of local parks. Hocking Hills State Park alone has 59 miles of trails just for hiking—and then you can add in the trails for horseback riding, rock climbing routes, bike paths, and caves to explore. Oh, and don’t forget the zip lines—there are more than 60 waiting for you. No matter where you are, you’re surrounded by nature.

That’s true for the local businesses, as well. Rockmill Brewery, for example, is on an old horse farm tucked in among the trees, and one of the main towns, Logan, is right alongside the tree line. There’s even a glass-blowing spot, Jack Pine Studio, that’s not only next to the woods, but brings nature into its designs. Every year, they have an annual glass pumpkin festival in the yard. Cabins and restaurants are in every wooded nook of Hocking Hills waiting for you to explore the surroundings.

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Where to Stay in Hocking Hills

Dive deep into this nature-based travel excursion when you check into Fox Fire cabin. The cabin is part of the Hocking Hills Cabins and Resort complex. Make sure to bring your friends because you’ll get the entire house, which sleeps up to 14 people in four bedrooms. The cabin is three stories tall, and each floor has its own bathroom.

Even though it’s a cabin in the woods, Fox Fire still offers modern amenities like Wi-Fi and smart TVs. There’s a game room on the lower level with a bar, a fire pit, a wraparound porch, a hot tub, a grill, and a fireplace.

Hocking Hills Cabins & Resort Foxfire

8.9 Excellent (23 reviews)

4. Embrace the Simple Life of Amish Country in Shipshewana, Indiana


Have you ever had Amish peanut butter? It’s this delicious mix of peanut butter and marshmallow fluff—sweet and savory at the same time and perfect drizzled over some French toast. If that sounds good, take a weekend away in Shipshewana, Indiana, in the heart of Amish country. Not only will you find that delectable peanut butter everywhere, you’ll also get to explore Amish specialties like hand-woven rugs, horse-drawn carriage rides, and helpful, happy attitudes.

Shipshewana has one of the largest Amish populations in the United States. The town is pretty sparsely populated—only about 950 people live there—but it drips with personality. You can learn more about the Amish and Mennonite cultures at the Menno-Hof Amish and Mennonite Museum in town, or even join a local family for a home-cooked meal. They’ll pick you up in a horse and buggy and help you experience what it really means to be in the Amish community.

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Where to Stay in Shipshewana

After dinner, head back to the Farmstead Inn and Conference Center, where you can sit outside and listen to the clip-clop of the horses and the rattle of the buggy wheels as they roll by. The rooms are fairly basic (and why wouldn’t they be in Amish Country) but there are a few suites and a cabin-themed room complete with local Amish-made furniture.

Right next door is the Red Barn, where guests can find the hotel’s indoor pool, kid’s pool, and hot tub, plus a basketball court, ping pong tables, and a fitness center. You can also rent a bike and explore the local trails, or sit in the on-site gazebo to enjoy a colorful sunset over the surrounding farms.

Farmstead Inn & Conference Center

Top rated
9.6 Excellent (2062 reviews)

5. Explore the Frank Lloyd Wright Architecture Capital, Oak Park, Illinois


Prairie-style architecture buffs will find an architectural wonderland in Oak Park, Illinois. It’s not Frank Lloyd Wright’s hometown (that’s in Wisconsin), but his home and studio is right in town.

After you go on a tour of those, walk up and down the village streets— you’ll find at least a dozen more Wright-built homes, all labeled with plaques. They aren’t open to the public like his home and studio, though; if you want to see inside some of the private homes, book your stay during Wright Plus Architectural Housewalk.

Oak Park’s location is a plus, as well. It’s literally right next to Chicago, but not in the city proper. You’ll find bigger lawns, space to move around, and less people vying for tables at restaurants or seats at events. And if you want to go into the city, it’s super easy—you can take public transportation. Both the buses and trains stop in the village; a one-way ride is only $2.50.

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Where to Stay in Oak Park

It may not be a Wright-designed home itself, but the Oak Park Beauty bungalow is a great place to stay for an authentic Oak Park home experience. The town sits in the Bungalow Belt, a ring around Chicago packed with historic bungalows. At this one, you’ll have the second floor to yourself, complete with three bedrooms and one full bath spread over 1,900 square feet. The kitchen is large and gourmet, and you can take your food out to a patio space overlooking a park. There’s also a grill out there, so if you want to have a cookout, you can.

Staycation Wright In Our Oak Park Beauty

Oak Park
9.4 Excellent (108 reviews)

6. Live Out Your Wild West Dreams in Deadwood, South Dakota


Wild Bill Hickok, Calamity Jane, Al Swearengen… for some they may just be names in a television show, but in Deadwood, they’re royalty. The three were actually real people that lived, fought, and survived in the Wild West in the Midwest town.

Today, Deadwood is an historical city and looks much the way it did back then. Though if you look past the surface, you’ll find more modern amenities like casinos—lots of casinos. It seems the gambling reputation of the town never left.

History is on display throughout the town, as well. You can visit the saloon where Wild Bill was shot during a game of poker and see his death chair. You can dine at the location of the notorious Gem Theatre, opened by Al Swearengen himself. You can even visit the graves of Deadwood superstars in Mount Moriah Cemetery next to downtown. Have kids with you? Check out the historical reenactments and get them a sheriff’s star from a local restaurant.

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Where to Stay in Deadwood

Embrace Deadwood history when you stay at the Iron Horse Inn. The building was originally a feed store in 1893, and just one story. Two more floors were added when the store transformed into the local post office. It later held a restaurant, and then in 1921, the property became a hotel. A casino was added in recent years. The suites and king rooms are decorated in an Old West style thanks to patterned wallpaper, but the other rooms are just as pleasant. Every room has standard amenities.

Iron Horse Inn

Top rated
9.0 Excellent (587 reviews)

7. Enjoy Big City Vibes With Less Crowds in Des Moines, Iowa


Des Moines, the capital city of Iowa, only has about 215,000 residents, but it has the feel of a big city. The downtown area is walkable and a nice place to sit with a meal on a patio and watch people go by. During busy months, you can take in a show or hit the robust farmers market— there’s room for 165 vendors, so you’ll always have a good selection of bakery, produce, fruit, and crafts.

To add to the big city feel, catch an Iowa Cubs game. They play at Principal Park right in the city and are the Triple-A affiliate for the Chicago Cubs. Des Moines was actually named the number-one minor league market, so it’s an excellent place to watch a high-quality game without Major League prices. Plus, the outdoors is never far away – the city has more than 800 miles of trails – great for hiking.

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Where to Stay in Des Moines

Bring the urban nature of Des Moines into your hotel when you stay at the Hotel Des Lux. It’s full of urban-inspired features, like exposed brickwork, and is right downtown—so you’re only ever minutes away from the action. The hotel rooms are the largest in the city and depending on your room, you’ll get an atrium, a fireplace, and a whirlpool, all decked out in modern style with large windows overlooking downtown.

Breakfast is included in your stay, and in the evenings you can grab a martini at the Des Lux Bar, a cocktail joint with a tin ceiling and retro- inspired decorations. The fitness center, in addition to a sauna, steamroom, and whirlpool, has full locker facilities, high-end LifeFitness equipment, and therapeutic massage on request.

Hotel Des Lux

Des Moines
9.6 Excellent (2034 reviews)

8. Walk Through Oregon Trail History in Independence, Missouri

One of the greatest things about traveling in this century is that we don’t have to do it in a covered wagon. But that doesn’t mean we shouldn’t honor the people who did and paved the way for us in the past. A stay in Independence, Missouri, will put you right at the start of the historic Oregon Trail. It’s no longer a small town on a square like it was when anxious travelers were loading up their wagons, though. Today, the small city has a population of just over 117,000.

But that doesn’t mean history isn’t available for you to explore. Oregon Trail aficionados should stop in to the National Frontier Trails Museum for a glimpse into what the pioneers endured. Stop by Independence Square to see where travelers stocked up their wagons and visit one of the last original buildings, the jail—it was built in 1859, at the heart of Oregon Trail season, and once imprisoned Jesse James’ brother. Next to the courthouse, you’ll find an Oregon Trail marker, pointing out the spot where the trail actually began.

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Where to Stay in Independence

If you want to stay in a home that was there when the Oregon Trail wagon trains were heading out, check into the Silver Heart Inn Bed and Breakfast. It was built in 1856 and has four rooms, plus two cottages. Each room is sumptuously decorated with antiques and old-world wallpaper and decorations, plus you’ll enjoy original architectural details in the rooms and throughout the house.

The cottages aren’t as historic but you get the whole place to yourself, including laundry facilities. On the Silver Heart Inn grounds, you’ll find a white picket fence, gardens, a fountain, and songbirds welcoming you throughout the day.

Silver Heart Inn Bed And Breakfast

Top rated
9.4 Excellent (193 reviews)