Taking a Midwest Road Trip? 26 Fun Family Destinations

Driving across the country along Route 66, up or down the Pacific Coast Highway, or the along the Road to Hana may be some of the most popular road trip itineraries, but don’t underestimate the options the rest of the country has to offer. Wayfinding TravelingMom Jennifer Kaufman is offering some of the best suggestions for Midwest road trip destinations.

You never know what kind of unique things you’ll find on a Midwest road trip… like the one-of-a-kind City Museum in St. Louis, Missouri! Photo Credit: Jennifer Kaufman, Wayfinding TravelingMom

Having lived in the Midwest my entire life, it’s sometimes entertaining to hear what other people think about the region. Heck, I get it. I grew up in Cincinnati, Ohio and still legitimately thought for much of my young life that the rest of the state was probably made up of towns with unpaved dirt roads. The Midwest may not be as flashy as some other vacation destinations, but there are things a Midwest road trip can offer that nowhere else can. Here are some of our favorite places to travel, as well as suggestions from other TravelingMoms.

Our State-by-State Guide to Rock Your Midwest Road Trip

Midwest Road Trip: Illinois Destinations

Chicago

We have taken countless trips to Chicago, and still I have no idea where to begin. I truly believe any Midwest road trip would be incomplete without a trip to the Windy City, but how you spend your time there is entirely up to you. Maybe you’d like to shop on the world famous “Magnificent ice,” Michigan Avenue’s shopping strip; don’t forget to stop in the American Girl Store, and maybe even grab a bite to eat in the American Girl restaurant. You could spend some time on the beach, or taking a boat tour on Lake Michigan – likely taking off from the family-friendly Navy Pier area. Check out some of TraveingMom’s favorite advice for a visit to Chicago.

Legoland Discovery Center

In Schaumburg, Illinois – a suburb of Chicago – you’ll find one of the country’s Legoland Discovery Centers. We were visiting friends in Chicago one year, when we quite literally stumbled on this gem. It’s not a full-fledged theme park like the Legoland parks you’ll find in Florida or California, but it was a super fun way to spend the day. We had fun building, racing lego cars, seeing how Lego bricks are made, and even riding a handful of great indoor attractions.

Midwest Road Trip: Indiana Destinations

Indiana Dunes

Indiana Dunes State Park has 15 miles of stunning beaches on the shore of Lake Michigan. The sand dunes and beautiful blue water look like something you’d see on the east coast – not in the middle of the Midwest. When you’re done playing on the beach, swimming, and going horseback riding, there are lots of craft breweries and local restaurants to hang out in during the evenings.

Indianapolis

Active TravelingMom Kimberly Tate loves Indianapolis’ White River State Park. She says, “It contains almost any activity a family could want. Head to the zoo, bike around the riverfront, or visit the NCAA Headquarters and Hall of Champions,” which Tate says offers some fun hands on play for tweens and teens. Indianapolis is also home to one of our family’s favorite children’s museums.

TravelingMom Tip: Don’t forget to check for reciprocity benefits if you have a membership to your local museum!

Santa Claus, Indiana / Holiday World

Spring break vacations might take you to Holiday World in Santa Claus, Indiana. — Holiday World and Splashin’ Safari make Santa Claus, Indiana a worthwhile visit! Photo: Sarah Gilliland, Twins TravelingMom

It’s Christmastime year-round in Santa Claus, Indiana. Write a letter to Santa at the post office, or spend the day at Holiday World – an entire theme park themed to Christmas! During the actual holiday season, visitors can find even more activities.

Valparaiso

Storyteller TravelingMom Mary Lebeau suggests you visit the college town that “caters to families, [including] popcorn festivals (as the birthplace of Orville Redenbacher), golf courses, and a drive-in movie theatre that’s over 60 years old.”

Midwest Road Trip: Iowa Destinations

Take a ride on the Boone & Scenic Valley Railroad in Central Iowa. — The Boone & Scenic Valley Railroad gives a unique perspective of Central Iowa. Photo credit: Renee Virata, Quick Weekender TravelingMom

Winterset

Traveling Grandmom Diana Rowe loves Winterset – the home of John Wayne, a super fun sculpture park, and fun, family-friendly railroad attractions. Central Iowa is also the inspiration for The Bridges of Madison County.

Midwest Road Trip: Kansas Destinations

Kansas City

Jamie Bartosch, Suburban TravelingMom, says Kansas City is the ideal Midwest destination for multigenerational road trips. Check out her recommendations for things to do, see, and eat there.

Midwest Road Trip: Michigan Destinations

As a resident of the Buckeye state, it’s my civic duty to hate “that state up north.” I promise I do, during football season, but I simply can’t extend my disdain for Michigan any farther than the football field. The reality is, it’s an absolutely breathtaking state – especially if you’re looking for outdoor destinations. Whether you’re visiting gorgeous beach towns on Lake Huron or spending the winter with sled dogs in Traverse City, there are too many delightful towns to visit in both the lower and upper peninsulas. The state also offers a few really unique destinations for your Midwest road trip.

Holland

a field of orange tulips in the foreground, with other colored flowers in the background — If you’re in Holland, Michigan at the right time, you can catch the Tulip Time Festival! Photo Credit: Jennifer Kaufman, Wayfinding TravelingMom

Holland, Michigan may be the closest thing you can get to the Netherlands, without traveling to Europe. A large, authentic Dutch windmill is perhaps the highlight of a visit to Holland; there are also Dutch restaurants, architecture tours, and even wooden shoe carving shows. If you visit in May, you’ll be treated to the Tulip Time Festival, too!

Mackinac Island

This no-cars-allowed island between Michigan’s upper and lower peninsulas might be the epitome of relaxation. Mackinac Island is also home to the United States’ second-ever National Park; Mackinac Island National Park is 70 acres of forests, incredible rock formations, wildlife, and beautiful water features, as well as historical and cultural landmarks.

Midwest Road Trip: Minnesota Destinations

Duluth

Duluth, like many of the Great Lakes towns on this list, offers lots of outdoor activities for families. It is also home to Great Lakes Aquarium, the only freshwater aquarium in the US.

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Minneapolis

Home to the Mall of America (which may be reason enough to visit), Minneapolis has so much to offer visitors. Explore the largest mall in the US, or enjoy a number of theater performances. Hike to Minnehaha Falls or explore miles of nature trails along the Mississippi River. Check out some of the fun free things to do in the Twin Cities!

Midwest Road Trip: Ohio Destinations

Cincinnati

Like the other large cities on this list, Cincinnati offers far too large a variety of attractions to really cover here. Travel and Leisure has named it one of the “Best Places to Visit” the last few years; world-class museums, one of the best zoos in the country, several professional sports teams, and a vast historical significance are only a handful of the things that draw visitors to the Queen City year after year. Check out our favorite family destinations here. We’ve also rounded up where to beat the heat without breaking the bank, free activities around the city, and even how you can camp with the giraffes at the Cincinnati Zoo!

Cleveland

The most famous attraction in Cleveland, Ohio is probably the Rock and Roll Hall of Fame and Museum. If you like music at all, you’ll enjoy a visit there. Even my kids, who didn’t know half of the artists, found plenty of interesting things to see and do. While you’re in Cleveland, you should also check out the beautifully revitalized Little Italy neighborhood or catch a Cavaliers game.

Hocking Hills

Travel less than an hour from Ohio’s capital city, and you’ll find yourself at the beginning of Appalachia. Hocking Hills State Park has some of the area’s best hiking for families, as well as many other outdoor adventures such as zip lining and rafting. We’ve taken young kids there on paved trails, or spent time on more difficult hikes with older kids and adults. The area is also home to caverns, waterfalls, lakes for boating and water sports, and cultural and historic attractions.

Sandusky/Lake Erie Shore

Sandusky, Ohio is home to Cedar Point – the flagship park of Cedar Fair. There are also four indoor waterpark resorts, and beautiful beaches along Lake Erie. From Sandusky, families can take ferries to Kelleys Island or South Bass Island’s Put-in-Bay. On these islands families can take cave tours, go on fishing excursions, or climb the Marblehead Lighthouse for spectacular views.

Warren County

North of Cincinnati, visit Mason, Ohio. Stay at Great Wolf Lodge and visit Kings Island amusement park next door – home of the “Best Children’s Area in the World” almost 20 years running.

twin girls walk alongside a cobblestone road in Historic Lebanon, Ohio — Historic Downtown Lebanon is filled with charming shops, world-renowned antiques shopping, and historical landmarks. Photo Credit: Jennifer Kaufman, Wayfinding TravelingMom

You can also take a scenic train ride to Lebanon, the county seat of Warren County – “Ohio’s Largest Playground”. Here you’ll find a charming downtown area with some of the country’s best antiques shopping. You can even dine – or stay overnight – at the Historic Golden Lamb Inn & Restaurant. Opened in 1803, the Golden Lamb has hosted 12 US presidents and dozens of other US and world dignitaries.

Midwest Road Trip: Missouri Destinations

Branson

DebtFreeTravelingMom Kathy Penny loves Branson, Mo because it’s “a fun and affordable vacation destination with something for everyone from beautiful lakes and mountains to fun shows and theme parks.” Silver Dollar City is a family-friendly theme park themed to an old mining town. Kids and adults of all ages can choose from more than 40 rides and live entertainment.

Lake of the Ozarks

Lake of the Ozarks has something for every kind of vacationer. “The Strip” offers your typical tourist fare: gift shops, arts and crafts, fudge and candy factories, and the like. But it’s the beautiful lake (with more than 50 marinas), collection of golf courses, horseback trails, boat tours through caverns, and tours of mansions (both current and historic) that will keep you busy for as long as you want to stay.

St. Louis

St. Louis is one of our family’s favorite getaway spots. Less than 6 hours from Cincinnati, Chicago, Indianapolis, Kansas City, Des Moines, Milwaukee, Louisville, Nashville, Tulsa, and Memphis, it may be the most centrally located destination on this list. Families should check out the Gateway Arch, but also Forest Park (larger than New York’s Central Park, and home to a free zoo and a number of free museums), the Anheuser-Busch Brewery and Grant’s Farm, and the eclectic, one-of-a-kind City Museum.

Texas TravelingMom Jill Robbins agrees, adding that St. Louis has “a really fun and trendy waterfront area (Laclede’s Landing), plus lots of stuff for the sports lover.”

Midwest Road Trip: Nebraska Destinations

Omaha

Dana Zucker, Luxe TravelingMom, recommends the Omaha Zoo – and touts Omaha as a must-do for foodies. Candid TravelingMom Patti Holliday adds, “The city is one of the nicest, cleanest, and most hospitable places – especially in the spring and summer, when the weather is perfection!”

Midwest Road Trip: North and South Dakota Destinations

Badlands National Park

Badlands National Park offers beautiful landscapes and protected wildlife.

Black Hills & Mount Rushmore

Black Hills, South Dakota, — The Black Hills offers plenty of hiking options, but National Parks TravelingMom Catherine Parker suggests exploring it by ATV. Photo Credit: Catherine Parker, National Parks TravelingMom

Mount Rushmore is carved into the side of the Black Hills Mountains, and draws more than 3 million visitors every year.

Midwest Road Trip: Wisconsin Destinations

Madison

Road Warrior TravelingMom Nasreen Stump says Madison, Wisconsin is her all-time favorite Midwest destination. She says it combines elements of Burlington, Vermont, Boston, MA, and Austin, TX into one location. Check out her suggestions for free family-friendly ideas in Madison!

Milwaukee

Milwaukee, Wisconsin combines a beautiful beach on Lake Michigan with the hustle and bustle of a growing city. Motorcycle fans can visit the Harley-Davidson Museum, and visitors can take part in several festivals throughout the year – including Summerfest, one of the world’s largest music festivals.

Wisconsin small town getaway adds walks in the woods to downtown village events. — Elkhart Lake is a beautiful, natural haven not far from the city of Milwaukee, Wisconsin. Photo Credit: Christine Tibbetts, Cultural Heritage TravelingMom

While traveling through the Milwaukee area, plan a trip to Elkhart Lake (about an hour east of the city). Maria Smith, TravelingMom of Many says it’s one of the best lake spots in the Midwest. With all of the beautiful towns along the Great Lakes, that’s saying something; she shares her extremely convincing argument here.

Wisconsin Dells

Wisconsin Dells has been dubbed the “water park capital of the world”, but there’s more to do there than just water slides. Much like a visit to Branson, Missouri or Gatlinburg, Tennessee, you’ll find a plethora of go-kart tracks, live dinner shows, and boat tours. Away from the hustle and bustle of those tourist destinations though, you’ll also find plenty of water sports and hiking in the Dells’ three nearby state parks.

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