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9 Best Midwest Road Trips [Getaways & Vacation Ideas]

9 Best Midwest Road Trips [Getaways & Vacation Ideas]

Midwest road trips make great weekend getaways with kids where you can make memories, strengthen family bonds and take fabulous photos to be treasured for years.

What makes Midwest road trips so great is the liberty of being on the road and the ability to stop at any time to explore.

An exit to see the world’s largest rocking chair? Don’t mind if we do! You’re also free to eat wherever and whatever you want. Pack picnic supplies, or buy them en route, and find a roadside park or a nice meadow to stop for lunch.

Or find a diner when you’re ready for a meal. You’ll find amazing pies at these places too. Some of the best barbecue you’ll ever eat will be in an out-of-the-way restaurant under a sign of a dancing, neon pig.

Bonus points if the pig is wearing a hat and sunglasses. You can’t do those things on a plane.

Airplanes, as much as we love them, are merely a mode of transportation--unless you’re flying to Dubai in one of those first-class suites with a shower.

But that’s not the point here. The point is a road trip is a part of the vacation as much as a visit to the city zoo, museum, festival, or grandma’s house. Midwest road trips are entertainment, education, and family time rolled into one fun, highway-led adventure.

So, where should you go? On the other hand, we suggest you avoid these mistakes  to have the best road trip with the kids

Midwest Vacations Road Trips

From Ohio to the Dakotas, the Midwest region of the United States is packed with monuments, parks, and, of course, lakes, great and small.

There are lots to do and see, especially straight from the comforts and freedom of the family truckster. Also, you need to know some information before you rent an RV.

Midwest road trips on winding roads at sunset

Travel Midwest and Discover Wisconsin

Use the Mississippi River as a natural guide for excellent Midwest road trips. Start where the St. Croix and Mississippi rivers meet in the pretty town of Prescott, Wisconsin.

From there, the National Scenic Byway will take you on a 250-mile-long tour of the Mighty Mississippi. If the kids are with you during the trip, we suggest that you give them books for kids to keep them busy.

Plenty of dining options are available along the way, from casual to upscale, like Chef Shack Bay City and the Driftless Cafe, both run by James Beard Award-nominated chefs.

The Wisconsin birthplace of Laura Ingalls Wilder, author of the classic Little House on the Prairie series, is in these parts too, located a few miles away from where the widest part of the river is called Lake Pepin.

Pass the numerous organic farms nestled in green, rolling countryside and consider their contributions to the nation’s tables.

View of the Mississippi River in Wisconsin

Wine-lovers must also hit some of the options for tastings and shopping on the Great River Road Wine Trail.

Getaways in Illinois on Route 66

A classic way to motor Midwest is by the king of all roads, Route 66. This iconic motorway starts in Chicago and winds all the way to the Santa Monica Pier.

Driving along Mother Road is indisputably a vacation in itself. The segment through Illinois to St. Louis is 300 miles of pure Americana. Take a family photo at the “Begin Route 66” sign outside of the Art Institute in Chicago.

Then head west for a stop at the Joliet Correctional Center, where Jake Blues was unfortunately incarcerated at the start of The Blues Brothers movie.

And make time to visit the Joliet Museum. In fact, the towns of Wilmington, Dwight, Odell, Pontiac, Bloomington, and Lincoln are all full of roadside attractions, famous birthplaces, and quirky museums.

You’ll also pass through President Abraham Lincoln’s old stomping grounds of Springfield. This section of Route 66 may end up being the longest 300 miles on earth because there’s so much to see.

The Pontiac-Oakland Auto Museum and the official Route 66 Hall of Fame Museum are in Pontiac. Then you’ll pull up to St. Louis where you can marvel at the Chain of Rocks pedestrian bridge that spans the Mississippi River.

Or, keep going west until you get to Santa Monica. Your choice! Ah, freedom.

Beginning of Route 66 in Chicago

Other Midwest Vacation Spots That are Can’t-Miss

Black Hills, South Dakota, is best accessible from Rapid City. This area definitely warrants a multi-day itinerary. From Rapid City, visit Wall--don’t miss a trip to Wall Drug--and venture into Badlands National Park. After your journey through this dramatic, rugged landscape, there’s a multitude of other awe-inspiring parks, trails, and sights.

You can’t miss Windcave National Park, Hot Springs, and Mammoth sites. Then continue to Keystone to start your exploration of Custer State Park.

You’ll also find opportunities to ditch the hiking boots and jump back into the car to take on the scenic byways of Iron Mountain Road, Needles Highway, and Custer Wildlife Loop Road.

Cap your Midwestern road trip adventures with a visit to the majestic Mount Rushmore. Did you know there are sand dunes in Indiana? Find them on the southern edge of Lake Michigan in Indiana Dunes National Park.

The park has 15 miles of beaches and dunes, breweries, and restaurants. There’s also lovely architectural history here that’s perfect to tour on Midwest road trips.

The Century of Progress homes is here, built after the Chicago World’s Fair in 1933. The boxy International Style homes were also inspired by the fair and you’ll see great examples of these beach-front vacation escapes of wealthy families from that time.

Make sure to drive beyond these iconic sites though to explore the old homesteads of Swedish immigrants who settled in Northern Indiana in the mid-1800s.

More Things to do in the Midwest

Roaring rivers and picturesque mountain ranges aren’t the only special features of the Midwest. Charming towns with wonderful food, wine, and craft beers are teeming with rich histories and fascinating museums and heritage sites.

Want to have more ideas for getaways? We compiled our list of the best road trips you and your family can take.

See Related: 10 Best Iowa Family Vacations to Take This Year

Midwest Family Vacations are Big Here

A Midwest road trip through North Dakota affords your family a big experience they’ll always remember. Jamestown, ND, is home to the National Buffalo Museum.

They can also boast the World’s Largest Buffalo Statue which is on the edge of the Old West-styled Frontier Village and pays tribute to the importance of bison and Native American culture to the Midwestern United States.

Fort Seward is a military fort, active from 1872 to 1877, and many artifacts are on display inside the fort. The buffalo statue, Frontier Village and Fort Seward are free to visit--perfectly family-friendly.

For another World’s Largest attraction, you could plan one of your Midwest road trips to see a giant boot. Red Wing Shoe Store and Museum in Red Wing, Minnesota, houses the largest boot in the world.

Such big boots will inspire you to tackle the area’s gorgeous bluffs on a hike. Back in town, enjoy craft beer, local wine, and unique Midwestern dishes.

On your drive out, swing by the Red Wing Arts Association in the train depot. Also, while on travel, it is a must to bring a travel cooler to stay hydrated.

Red Wing is by far one of the best things to do in Minnesota. It’s a charming small town located along the Great River Road scenic byway.

More Family Trip Ideas for Minnesota

The birthplace of the Mississippi River and known for its Twin Cities of Minneapolis and St. Paul, friendly Minnesota contains a trove of family trip ideas. One of the most classic Midwest road trips can take you along the North Shore of Lake Superior, from Duluth up to Canada.

North Shore, Minnesota | Top Things to Do [4K HD]
Watch this video on YouTube.

The roadway is designated as an All-American Road. Along the way, you’ll see the rocky, sandy beaches of dynamic Lake Superior, which is the largest of the Great Lakes. Find opportunities to hike at Lutsen Resort and at Gunflint Trail.

You can also plan stops at Gooseberry Falls State Park for a look at the gorgeous waterfalls, and at Devil’s Kettle Falls to see the phenomenon of the disappearing Brule River.

Your Midwest road trip will end at Minnesota’s highest waterfall in Grand Portage State Park at the Canadian border. Pick one of three decks for a breathtaking view.

See Related: Best Minnesota Family Vacation Ideas 

Michigan Family Vacations in the Midwest

Shores of Saugatuck Dunes State Park

The Southwest region of Michigan is another worthwhile Midwest road trip to take as a family vacation. The towns aren’t too distanced and there are lots to do for the whole family.

Plan to spend a couple of days exploring Saugatuck. There’s a beautiful beach at Saugatuck Dunes State Park. Hike the woods and climb up a sand dune.

You’ll be ready for a cold-water plunge afterward in bracing Lake Michigan. Spend the next day in town ogling fancy yachts, eating ice cream, and window shopping at the boutiques.

Pile back into the car and head up a short way to take in the charm of Dutch-themed Holland. Windmill Island Gardens and Holland State Park will win you over to the Dutch side.

Admission to both attractions is free. Your next stop is Sleepy Hollow State Park in Laingsburg. Its 2,600 acres contain a winding river and Lake Ovid.

There are plenty of activities here a family can enjoy, including bird watching and trails. You’ll end up in Lansing, Michigan’s state capital. Take a tour of the gilded downtown capitol or visit the Michigan History Center.

Another amazing Midwest road trip in the great state of Michigan will have a portion with no road at all. Mackinac Island is only accessible by ferry.

Once you’re there, it’s only bicycles, horses, and your own feet for travel. But the drive along I-75 to get to Mackinaw City and the ferry docks will take you through the rolling countryside and pretty towns of Michigan.

Mackinac Island as a destination is one of the best family vacations in the Midwest. On the other hand, we created the ultimate guide for your California road trip – if you have that in mind.

Weekend Getaways in the Midwest

Big family vacations aren’t always the answer to wanderlust. Sometimes weekend getaways in the Midwest are all you need to rejuvenate.

Best Midwest Cities for a Weekend Getaway

Pack some snacks, an overnight bag, and gas up the car. These weekend getaways in the Midwest will make great road trips. Make Wichita, Kansas, your final destination and enjoy a vibrant arts scene, great restaurants, and more than 100 parks.

You need a family picture at the Keeper of the Plains monument, of course. But after that, occupy yourselves with excursions to the Old Cowtown Museum and Botanica Wichita.

If you’re a family of foodies, you’ll want to steer southwest of Indianapolis to Bloomington. After sampling the fresh farm-to-table fare, you can take your exercise on one of the surrounding hiking and biking trails, like those in Hoosier National Forest.

Bring one of these travel kettles along on your journey.

Best Family Road Trips Midwest / Great Lakes Area for the Weekend

Kenosha, Wisconsin, sits prettily on the shores of Lake Michigan and is a weekender’s paradise. Relaxing and sailing is the preferred lifestyle here. But you can’t miss a ride on the electric streetcars or the sculpture walk.

Tell folks at home about the time you rode a bike on the oldest working velodrome in the US right here in Kenosha—the Washington Park Velodrome. Sample the famous cheeses of Wisconsin at Mar’s Cheese Castle. You’ll also want to save some time to visit the town’s museums and history centers.

Found on Lake Erie, Sandusky, Ohio, is well known for Cedar Point amusement park (the Roller Coaster Capital of the World), which is super fun for families.

But there’re other things to do when you don’t feel like spending your precious weekend hours waiting in lines. Take the ferry to Put-In-Bay and spend the day exploring, touring, sailing, golfing…whatever floats your boat. There’s also great dining and wine tasting.

Back in Sandusky, give the town’s other waterparks and amusements a spin. Learn about Ohio’s boating history at the Maritime Museum of Sandusky.

Finally, spend a delightful afternoon seeing how carousels are restored and riding a few of them at Sandusky’s whimsical Merry-Go-Round Museum.

See Related: How to Visit the Buddy Holly Crash Site

Best Road Trips in the Midwest Exploring the Ozarks in a Weekend

If you’re planning for a Midwest road trip in Missouri, you’re in luck. The Ozark Mountains provide a playground of trails, rivers, and lakes and simply beautiful scenery perfect for driving to or through.

There are more than 300 miles of winding, forest roads. The area was once covered in water and you can learn more about what this ancient sea looked like with a trip to the Onondaga Caves.

Rent a log cabin or tent camp in the Mark Twain National Forest and make sure to contemplate a portion of the Trail of Tears at the Indian Trail Conservation Area.  For another fun option, cue up your Andy Williams playlist and drive to Branson, MO, for family-friendly shows and museums.

Endless outdoor activities are minutes away in the Ozarks’ lakes and mountains. If you venture a couple of hours east on US-160E from Branson, you can scout the “Little Grand Canyon” of Grand Gulf State Park.

This natural wonder is a collapsed cave system, stretching for almost a mile between 130-foot high walls. The best viewing is from the trails at the top of the gulf. More adventurous types can scramble to the floor for a walk under the 250-long natural bridge.

See Related: Best Things to Do in Warsaw, Indiana

Many Great Places to See in the Midwest For Your Next Road Trip

Fly over this country? Not when gorgeous natural beauty spreads from Lake Erie to the High Plains before the Rockies rise and the West officially begins. The best way to see it all is by a Midwest road trip and these sights and places will show you all the Midwest has to offer.

Take a weekend at a time or block off a week, or even two, to visit the cities, towns, and villages that give the Midwest its friendly charm. Cool lakes and timeworn mountains provide limitless activity and entertainment, while sunny farmland yields the freshest flavors only miles from the dining table.

Whether you like slow, meandering cruises through rolling hills or high-flying roller coasters, the Midwest delivers.

There’s guaranteed to be something interesting to see and do for every member of the family. Hiking, swimming, camping, skiing, seeing museums, exploring lighthouses, or just soaking up the sights from the top of a gorge will leave you appreciating the wildness to be found between the coasts.

With so many great places to see in the Midwest, where will you go for your next road trip?

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