Skip to Content

11 Best Midwest Road Trips [Getaways & Vacation Ideas]

We take pride in providing authentic travel recommendations based on our own experiences such as unique images and perspectives. We may earn a commission when you purchase a product or book a reservation. Learn more ›

The Midwest region of the United States stretches from Ohio to the Dakotas. It’s packed with monuments, parks, and lots of lakes, great and small.

Midwest road trips make great getaways for families, whether for multiple weeks or a weekend. Road trips are perfect occasions for everyone to make memories, strengthen bonds of family and friendship, and take fabulous photos which will be treasured for years.

There’s plenty to do and see throughout the Midwest, especially while observing the scenery from the comforts and freedom of your own’ family truckster.’ (A reference directly from “Vacation” — a favorite road trip movie!) Or you can rent a larger rig to get around, but it helps to do a lot of research when considering renting an RV.

Whether a weekend or a 7-day Midwest road trip, these vacations provide all sorts of freedom to be out on the open road, enjoying endless opportunities of things to see plus so many places to pull over and pull out the camera.

An upcoming exit promising the world’s largest rocking chair? Don’t mind if we do! You’re also free to eat wherever and whatever you want, including all sorts of tasty, hearty, and uniquely Midwestern culinary treats, including cheese curds, bratwursts, and lots of gravy.

If you’re ready for something more robust, Midwest barbecue is legendary and can be found just about anywhere. A good clue you’re in the right place is signage featuring a dancing, neon pig. Bonus if the pig is wearing a chef hat and sunglasses. You can’t get that kind of experience on an airplane!

A road trip is an essential part of any modern vacation experience as much as a local visit to the city zoo, a museum, a festival, or even grandma’s house. Midwest road trips pack all sorts of entertainment, education, and family time into one fun, mobile adventure.

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

So, where should you go on your next Midwest family vacation? What kind of Midwest road trip ideas do you have, and what natural wonders do you want to see?

And just as important, how do you avoid mistakes to ensure you have the best road trip with the kids? Continue reading for some super suggestions.

(If our list of ideas for the best Midwest road trips isn’t enough, we’ve compiled an even more comprehensive list of the best road trips anywhere you and your family can take.)

Midwest Vacations Road Trips

1. Travel Midwest starting with Wisconsin cuisine and the big rivers

View of the Mississippi River in Wisconsin

Consider using the Mississippi River as a natural starting point for excellent Midwest road trips. Launch your journey 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 Mississippi. If you have little passengers who might be tired of the scenery, we suggest you hand out travel-themed books for kids to keep them occupied.

Plenty of dining options are available along this route, 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 book series, is located a few miles away from the widest part of the river, at Lake Pepin.

Traverse the numerous organic farms nestled in green, rolling countryside and consider their contributions to the nation’s kitchens. Wine lovers will enjoy checking out some of the options for tastings and shopping on the Great River Road Wine Trail.

See Related: Cheapest Shopping Destinations in the World

2. Midwest Getaways in Illinois along Route 66

Beginning of Route 66 in Chicago

A classic way to motor through the Midwest is by taking Route 66, nicknamed ‘the king of all highways.’ This iconic motorway starts in Chicago and winds all the way west to the Santa Monica Pier in California.

Driving the Mother Road, another nickname for 66, is a memorable experience, whether you drive the whole thing or take segments, such as the 300-mile stretch through Illinois to St. Louis, where you’ll encounter nothing but pure Americana. Before you head out, be sure to snap a family photo at the “Begin Route 66” sign outside of the Art Institute in Chicago.

As you head west following your list of Midwest road trip ideas, stop by the Joliet Correctional Center, pictured at the beginning of “The Blues Brothers,” where Jake Blues was incarcerated.

Nearby is the Joliet Museum, the first of many roadside attractions, quirky museums, and famous birthplaces awaiting in the towns of Wilmington, Dwight, Odell, Pontiac, Bloomington, and Lincoln.

You’ll pass through President Abraham Lincoln’s old stomping grounds of Springfield, the state’s capital city.  Of course, your accommodations at the Abraham Lincoln Doubletree Hotel are definitely more luxurious than his early days in the family cabin.

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.

See Related: Best All-Inclusive Resorts Without a Passport

3. Can’t-Miss Midwest Vacation Spots in South Dakota

Sioux Falls, South Dakota Scenery

The Black Hills area in South Dakota, where many of the more prominent tourist attractions can be found, is best accessible from Rapid City. This area warrants a multi-day itinerary for Midwest road trips for families.

Cap your road trips in the Midwest with a visit to the majestic Mount Rushmore, where the faces of four past U.S. presidents are carved into the mountainside. Nearby is the Crazy Horse Memorial, another historical figure currently being chiseled out of rock.

From Rapid City, don’t miss a trip to Wall Drug, and then venture into the Badlands area for more tours. After your journey through this dramatic, rugged landscape of the Badlands National Park in South Dakota, there are many other awe-inspiring parks, hiking trails, and sites, including Wind Cave National Park, Hot Springs, and Mammoth sites.

Continue to Keystone to start your exploration of Custer State Park, which provides illumination into a significant 19th-century battle.

After exploring 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, the first of many Midwest road trip loop opportunities.

4. Must-see Midwest Family Vacations in North Dakota

North Dakota Badlands Scenery

A Midwest road trip through North Dakota affords your family an amazing experience they’ll always remember, including Jamestown, home to the National Buffalo Museum.

Here, kids (and maybe parents, too!) can boast about seeing the World’s Largest Buffalo Monument on the edge of the Old West-styled Frontier Village. The place pays tribute to the importance of bison and Native American culture to North Dakota and the Midwestern United States.

Fort Seward, also in Jamestown, was active from 1872 to 1877, and today, many artifacts remain on display inside the fort. The buffalo statue, Frontier Village, and Fort Seward are free to visit. The Jamestown My Place is nearby, making planning your North Dakota sight-seeing easy.

See Related: Ways to Book the Cheapest First Class Flights

5. Family Trip Ideas for Minnesota

St. Paul, Minnesota Night Lights

The source of the Mississippi River, known for the Twin Cities of Minneapolis and St. Paul, Minnesota, contains a trove of family trip ideas, and there’s also no shortage of items vying for the title of the best things to do in Minnesota.

A classic Midwest road trip loop takes you along the North Shore of Lake Superior, from Duluth to Canada.

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

Your best Midwest road trip list can include stops at Gooseberry Falls State Park for a look at gorgeous waterfalls and Devil’s Kettle Falls to see the phenomenon of the disappearing Brule River.

Unless you’ve brought your passport, you’ll have to turn around from your northern journey at Minnesota’s highest waterfall in Grand Portage State Park, right at the Canadian border. Pick one of three decks for a breathtaking view.

If you continue checking off all your “World’s Largest” attractions on your Midwest road trip itinerary, prepare for The World’s Largest Boot, which is found only at the Red Wing Shoe Store and Museum in Red Wing. (It’s size 638-D if you were curious.)

Perhaps getting about big boots will inspire you to get your own to tackle the area’s gorgeous bluffs on a hike. Be sure to bring a travel cooler to stay hydrated.

Then, when you’re back in town, enjoy craft beer, local wine, and unique Midwestern dishes. You’ll find that Red Wing is a charming small town located along the Great River Road scenic byway. Stay overnight at the St. James Hotel, and on your drive out, swing by the Red Wing Arts Association, located in the train depot.

See Related: Minnesota Family Vacation Ideas 

6. Michigan Family Vacations in the Midwest

Shores of Saugatuck Dunes State Park

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

Plan to spend a few days exploring Saugatuck, including 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. Holland State Park will provide plenty of scenery to appreciate.

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

Plenty of activities here, including birdwatching and walking and hiking trails. You’ll end up in Lansing, Michigan’s state capital. Tour the gilded downtown capitol or visit the Michigan History Center.

Another amazing Midwest road trip in Michigan doesn’t even have a road to get to: take the ferry to Mackinac Island. Once there, you can get around with bicycles, horses, or your feet. The drive along I-75 to Mackinaw City and the ferry docks takes you through the rolling countryside and pretty towns.

Mackinac Island is considered one of the best family vacation spots in the Midwest. (Of course, there are certainly other parts of the country with unique charm, especially this ultimate guide to California road trips.)

7. Midwest Weekend Getaway Ideas can include Kansas

Topeka, Kansas Cityscape

Extended family vacations or even a 7-day Midwest road trip aren’t always the answer to wanderlust. Sometimes weekend getaways in the Midwest are all you need to rejuvenate.

Pack some snacks and your overnight bags, 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 over 100 parks.

You need a family picture at the Keeper of the Plains monument. After that, occupy yourselves with excursions to the Old Cowtown Museum and Botanica Wichita. Bring one of these travel kettles along on your journey.

Kansas City is also worth seeing, both the Kansas version and the Missouri one. Kansas City, Kansas, also boasts the Kansas Speedway, a NASCAR track. Remember, Dorothy wanted to return home to Kansas even after seeing the wonders of Oz!

8. Check out the Great Lakes Area

Kenosha, Wisconsin Scenery

Kenosha, Wisconsin, sits along the shores of Lake Michigan and is a weekender’s paradise. Relaxing and sailing is the preferred lifestyle here, and there isn’t much better locally on the electric streetcars or the sculpture walk.

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

The attraction of the Great Lakes extends to Ohio, including Sandusky, right on Lake Erie. The city is also known as the home of Cedar Point amusement park and the title of the Roller Coaster Capital of the World.)

If your schedule doesn’t accommodate waiting in theme park 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 or learn about Ohio’s boating history at the Maritime Museum of Sandusky. You can even combine fun with lodging since some nearby hotels have indoor water parks, such as the Cedar Point Castaway Bay Hotel.

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

See Related: How to Visit the Buddy Holly Crash Site

9. Explore the Ozarks and Other Missouri Sights

Ozark Mountain Views

You’re in luck if you plan a Midwest road trip in Missouri. The Ozark Mountains provide a wonderful natural playground of trails, rivers, and lakes. Its beautiful scenery is perfect for driving to or through, with more than 300 miles of winding forest roads.

The area was once covered in water. You can learn more about this ancient sea’s appearance with a trip to the Onondaga Caves.

Rent a log cabin or tent camp in the Mark Twain National Forest and contemplate a portion of the Trail of Tears at the Indian Trail Conservation Area.  Cue up your Andy Williams playlist and drive to Branson in Missouri for family-friendly shows and museums.

Endless outdoor activities and natural beauty 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 scramble to the floor for a walk under the 250-long natural bridge.

One highlight of Kansas City in Missouri is the National WWI Museum and Memorial.

10. Take a Trip to Indiana

Indianapolis Cityscape

Don’t forget that there are great things to the east of the Dakotas and Wisconsin, like… sand dunes? Yes, you’ve heard it right! You’ll find these unique geologic features on the southern edge of Lake Michigan in Indiana Dunes National Park.

The park boasts 15 miles of beaches, dunes, breweries, and restaurants. There’s also lovely architectural history throughout the region that’s perfect for Midwest road trips.

The Century of Progress homes are also nearby the Indiana Dunes National Park, built after the Chicago World’s Fair in 1933. The fair also inspired the boxy International Style homes. Take a peek to see great examples of these beach-front vacation escapes of wealthy families from that era.

Then, explore the old homesteads of Swedish immigrants who settled in Northern Indiana in the mid-1800s. If you’re a family of foodies, steer southwest of Indianapolis to Bloomington.

After sampling the fresh farm-to-table fare, you can exercise on one of the surrounding hiking and biking trails, like those in Hoosier National Forest.

See Related: Things to Do in Warsaw, Indiana

11. Iowa Beckons with Lots of Midwest Charm

Des Moines Cityscape

A deep appreciation for corn and pork is just the starting place for fun in the Hawkeye state. Iowa ranks high in overall friendliness and scenery, including the capital of Des Moines.

If you’re planning a future Midwest road trip for families, consider doing so in August, when the state fair in Des Moines occurs. It’s one of the oldest and largest events of its kind at the national level.

It lasts over a week, so you can stay for a couple of days at the nearby Hotel Fort Des Moines Curio Collection by Hilton. It’s also close to the Science Center of Iowa, Pappajohn Sculpture Park, and other mainstream attractions in downtown Des Moines.

Movie buffs will love visiting Iowa for different reasons. Iowa locations have been prominent in a variety of films, including “The Bridges of Madison County,” “Field of Dreams,” and (in a way) “The Music Man”. River City was based on Mason City!

The state always looks good, including the gold on the Capitol Dome. If you’re not heading through this part of the state, stick to the western or eastern borders. To the west, the Loess Hills make for a unique excursion into the not-so-flat plains.

To the east, Dubuque sits on the Mississippi River, offering a historic old port packed with activity. Be sure to visit the National Museum of the Mississippi River!

So Many Great Midwest Road Trip Ideas

If you fly over the American heartland in a plane, you’ll miss out on many gorgeous natural wonders of the Midwest, which spread 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 or even a Midwest road trip loop to see a lot and then head back home while seeing more along the way.

Take a weekend at a time or block off a week for a 7-day Midwest road trip, maybe two (three?) to visit so many special cities, towns, villages, and state parks that give the Midwest its friendly charm. Cool lakes and timeworn mountains provide limitless activity and entertainment, while sunny farmland yields the freshest flavors.

Whether you like slow, meandering cruises through rolling hills or high-flying roller coasters, the Midwest delivers. There’s guaranteed something interesting to see and do on Midwest road trips for families when you start thinking of your Midwest road trip ideas.

Hiking, swimming, camping, skiing, seeing museums, exploring lighthouses (yes, they are a thing!), visiting a special state park, or just soaking up the sights from the top of a gorge will leave you appreciating the wonder found between the coasts.

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


How cold does it get in the Midwest?

Be sure to pack your cold-weather gear. Except for Alaska, the wide-open plains lead the U.S. regarding cold weather resources. States like Wisconsin and North Dakota also make lists of the coldest cities, with an average daily temperature of 41 degrees throughout the year. A national park in the Midwest may be warm in the daytime but can cool down fast in the spring, fall, and even late summer.

What is Midwest food?

It depends on the state, but this style of food is often described as hearty, perhaps inspired by the meals cooked by early farmers and homesteaders. So, lots of butter and gravy. Each town may have its special place, be it BBQ or brats.  

What’s the best museum in the Midwest?

The venerable institutions in New York usually sweep these advertising competitions out of tradition and elegance. But few people realize that the Cleveland Museum of Art is one of the best-regarded institutions in the Midwest.

Related Product Guides

Related Resources

Leave a comment

Your email address will not be published. Required fields are marked *

    ↑ Top