Midwest Road Trips

Roll down your windows, feel the breeze and prepare for an adventure that’s as vast and varied as the Midwest sky. Welcome to our guide on the best Midwest road trips for families, where every turn uncovers a new surprise – be it a agricultural gem in Wisconsin, a construction loving kids’ dream in Illinois, a wonder filled aquarium in Iowa, a cascading waterfall in Minnesota, a sandy dune in Michigan, a bustling speedway in Indiana, or a majestic arch in Missouri. 

As we journey through these seven states, we’ll discover that the Midwest is not just “fly-over” country. No, my friends, it’s drive-through country! Buckle up, grab your snacks, and let’s hit the road. 

Prepare to experience the charm, beauty, and hidden gems of this remarkable region with our tried and true list of family-friendly Midwest road trips.

Sheboygan to Mackinac Island 

From Sheboygan’s lakeside charm to the timeless allure of Mackinac Island and beyond, this Midwest Road Trip itinerary stitches together several of Wisconsin and Michigan’s top destinations

Wisconsin Stops

The first stop will be in Sheboygan, home to the Bookworm Gardens, a magical, literature-inspired botanical garden where your children’s favorite stories come alive among lush flowers and whimsical sculptures.

As you journey onward, visit Titletown in Green Bay, where kids can scramble up Ariens Hill, conquer three playscapes, play ball on a full size football field and parents can relax with a local brew in hand.

Upper Michigan Stops

As the route carries you into Michigan’s Upper Peninsula, you’ll pass through Escanaba, a quaint harbor town where fresh whitefish is always on the menu. Stop into town for Swedish Pancakes at the Swedish Pantry and walk across the street to pickup some fresh homemade fudge.

Not far from here lies Kitch-iti-kipi, Michigan’s largest natural freshwater spring, where crystal clear waters offer a window into an underwater world teeming with trout. It is suitably nicknamed “mirror of heaven” and well worth the 30 minute detour it adds to your drive time. There is a small viewing raft you can ride to the center of the spring to gaze into the depths of the spring below. (Free.)

As you continue your journey, you’ll be in awe of the stunning beauty of Pictured Rocks National Seashore and the breathtaking power of Tahquamenon Waterfall.

And finally, you’ll arrive at the highlight of the trip – the incredible Mackinac Island. Imagine stepping back in time as horse-drawn carriages clatter along cobblestone streets, and the aroma of world-famous fudge wafts through the air. Reaching the island requires a ferry ride from Mackinac City.

Insider travel tip: If you are prepared to splurge, the Grand Hotel is the crown jewel of the island. It dons the world’s largest front porch.

The adventure doesn’t have to end there. This is a choose your own adventure decision point as it is about the same amount of travel time to turn around and return the same way. Or we’ll continue south and take a ferry across to Manitowoc.

Mainland Michigan Stops

If you chose the latter, the next stop is Petoskey State Park, where the kids can scour the shores for Michigan’s state stone, the Petoskey. My kids think they look like dinosaur eggs.

Then, it’s on to Sleeping Bear Dunes for a heart-pumping climb and a stunning view over Lake Michigan.

As twilight descends, pull into the Cherry Bowl Drive-In Theater for a dose of nostalgia and a family movie under the stars.

The journey concludes with a relaxing ferry ride across Lake Michigan from the Ludington Ferry Terminal, winding down a road trip that’s sure to etch itself into your family’s core memory bank.

What are you waiting for? Pack up the car and create some memories on one of our favorite Midwest road trips!

Milwaukee to St. Louis

Embarking on a road trip from Milwaukee to St. Louis is a journey filled with diverse landscapes, charming small towns, and iconic landmarks. The distance of about 375 miles offers a unique blend of urban hustle and rural tranquility with endless educational opportunities.

The Gateway City’s vibrant food scene and family-friendly attractions made St. Louis a laid back and unforgettable family getaway. 

I have a detailed post with all of our favorite stops along this route.  Check out our suggestions on how to break up the 6 hour trip between Milwaukee and St. Louis

Wausau to Duluth

This Midwest road trip itinerary starts from Wausau and you’ll make your way to enchanting Duluth, experiencing the natural beauty of the region along the way.

Get ready to explore stunning attractions like Copper Falls State Park, Apostle Islands National Seashore, and Amnicon Falls State Park.

But that’s not all! Our journey doesn’t end there. We’ll also visit Gooseberry Falls State Park and Split Rock Lighthouse State Park, just outside Duluth. And let’s not forget the vibrant cities we’ll encounter, like Duluth itself. Don’t miss out on the Lake Superior Railroad Museum and Great Lakes Aquarium!

This trip is perfect for both kids and adults, promising an unforgettable adventure through the Midwest’s charming towns and breathtaking landscapes. Click here for the full route and guide.

Milwaukee, Wisconsin to Holland, Michigan

I grew up on the west side of Lake Michigan and didn’t experience a sunset over the Great Lake until I was in my 30s. It is something to behold, I felt as if I was on a soft sandy beach on the Gulf of Mexico.

If you love sand, sunsets, beer, and charming towns, this Midwest Road Trip is for you.

Welcome to our road trip adventure from the bustling city of Milwaukee to the charming town of Holland, Michigan. Each stop along our journey offers its unique blend of attractions that both children and adults will adore.

In Holland, enjoy the town’s rich Dutch heritage, marvel at the authentic windmill at Windmill Island Gardens and savoring a pint or two from the local breweries, while the kids enjoy root beer and pretzels.

Saugatuck is famed for its Oval Beach, one of the top 25 beaches in the world, as ranked by Condé Nast Traveler, is a haven of golden sands and crystal clear waters.

South Haven and St. Joseph, with their picturesque lighthouses and serene beaches, offer a tranquil escape, while the Southwest Michigan Wine Trail is a feast for the senses, boasting some of the region’s finest wineries. The vineyards also offer grape juice tasting for the young ones, making it a fun-filled family experience.

Finally, the Indiana Dunes, with their towering sand dunes and diverse wildlife, offer a perfect mix of education and recreation. It’s a place where children can learn about nature while running free, building sandcastles, and splashing in the water.

Central Wisconsin Gems

Central Wisconsin, with its well kept secrets of natural beauty, rich history, and family-friendly attractions, is the perfect route for an unforgettable road trip.

Start your journey in Oshkosh, where you’ll find the delightful, free Menominee Park and Zoo, a favorite among families. While in Oshkosh, consider grabbing a lunch at a drive in diner with carhops on roller-skates; Ardy and Ed’s.

Just up the road, you’ll find iconic Wisconsin breweries, like Central Waters Brewing and Steven’s Point Brewery (one of the oldest in the country).

Next, immerse yourselves in nature at Schmeeckle Reserve’s tranquil trails and marvel at the mystically quirky Rudolph Grotto Gardens. Next, visit Jurustic Park, home to a fascinating collection of ‘prehistoric’ metal sculptures. Rudolph Grotto Gardens and Jurustic are both one of a kind attractions, so unique that they’ve been featured in Atlas Obscura!

As you head south, don’t pass Osseo without tasting the legendary pies at Norske Nook!

Experience the thrill of harvest season at Wetherby Cranberry Farm, then head to Wisconsin Dells, the “Waterpark Capital of the World“.

Continue your journey at the Ishnala Supper Club, offering mouthwatering dishes amid breathtaking views. You can expect to wait for a table so your best bet is to arrive when they open at 3:30 on weekdays. (Closed during the winter.)

Head next door to explore the serene beauty of Mirror Lake State Park and the magic of the Baraboo Circus Museum.

Go for a hike! Check out Parfrey’s Glen, Devil’s Lake, or Pewit’s Nest, each offering its own unique charm.

Don’t miss the Merrimac Ferry, Wisconsin’s only free ferry, before ending your Wisconsin Midwest road trip.

COVID and my parents’ collective health kept me close to home for a couple years which gave me the opportunity to explore my home state and discover gems I’d never expected; many of my favorites are on this route.

Milwaukee to Dubuque

A road trip that combines the charm of small-town America, the thrill of outdoor adventures, and the childhood excitement of interactive museums.

As you drive west through Wisconsin, the landscape transforms from urban sprawl to scenic countryside, with the Toy Train Barn Museum being your first stop. Featured in Atlas Obscura, this hidden gem houses a fascinating collection of miniature trains that will ignite your children’s imaginations. The best part about it is chatting with the couple who owns the museum. The man is a genius and the wife a saint.

Next, defy the laws of physics at Gravity Hill, a mysterious spot where your car will seem to roll uphill. It’s a strange phenomenon caused by optimal illusion.

Prepare to laugh with your whole family during your unusual hiking experience with goats in Galena, IL.

The Alpine Slide near Rice is a thrilling ride down a 2,050-foot track. Dubuque’s River Museum and Aquarium offers an immersive look at the Mississippi’s aquatic life.

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On a rainy day, the Creative Adventure Lab in Dubuque provides the perfect indoor escape with interactive exhibits designed to spark creativity.

And for a touch of history, take a ride on the Fenelon Place Elevator, one of the world’s shortest and steepest scenic railways.

A detour to the Field of Dreams movie site is a must for any baseball fan. And when you arrive at the Quad Cities, where the Family Museum in Davenport and the John Deere Pavilion in Moline offer educational and entertaining diversions.

End your day with a meal at Twin Span Brewing, recommended for its craft beers and kid-friendly atmosphere.

The final leg of your journey takes you back to Milwaukee, with a pit stop at the Children’s Museum in Rockford.

Join me as we delve deeper into each destination, uncovering more of what makes this Midwest road trip a fantastic choice for families looking for educational and unforgettable memories.

Milwaukee to Minneapolis

Minnesota’s Twin Cities, Minneapolis and St. Paul are chock full of family friendly attractions that won’t break the bank. 

There’s much to see along the Midwest road trip route to the Twin Cities so consider breaking up your journey with one or more of these kid-approved stops packed with intrigue, energy busters, and delicious food. 

Roadside Stops:

Run out some energy at Aztalan State Park near Johnson Creek before cranking out a big chunk of the route.  While the little ones are running, big kids and adults can soak in the rich history of one of the state’s most significant archaeological sites.   

This National Historic Landmark showcases  an ancient Middle-Mississippian village that thrived between A.D. 1000 and 1300. The settlement was mysteriously abandoned sometime between 1200 and 1300 CE, leaving behind a wealth of cultural artifacts and historical intrigue. The name ‘Aztalan’ was given by early settlers who mistakenly believed the site had links to the Aztecs.

Restock your car snack supply and taste the abundant cheese and fudge samples in this fun Wisconsin shop with a giant mouse called Mousehouse Cheesehaus.

Madison, Wisconsin

Take a brief detour to find Madison Family Fun. You’ll find a handful of family-friendly activities that can be completed in less than two hours.

A quick stop at the Henry Vilas Zoo, which offers free admission, is a must-do. It’s home to hundreds of exotic species from around the globe and also includes a children’s zoo and a carousel. Spend an hour or two at the Madison Children’s Museum, a hands-on learning experience that encourages curiosity and imagination with exhibits on art, culture, and science. For outdoorsy families, a stroll through the Olbrich Botanical Gardens offers stunning visuals with a variety of beautiful themed gardens.

Lastly, you could treat the kids to a scoop of homemade ice cream at the Memorial Union Terrace, while enjoying lakeside views of Lake Mendota.

Wisconsin Dells, Wisconsin

Family fun is plentiful in Wisconsin Dells. With so many options to choose from, it’s a challenge to pick just one destination for a road trip stop. However, here are a few places that have been excellent pit stops for our family while passing through.

Go Karting – Give your adrenaline loving kid a thrill that doesn’t consume much time at all!  Stop by Adare or Big Chief Go Karts for a quick race.

Mini Golf – Play a round of themed mini golf at Pirate’s Cove Adventure Golf to get the whole family some sunshine, movement, and healthy competition.  Lunch or Dinner – Choose a place with fun and unique vibes for a meal break.   We like The Grateful Shed (indoor food trucks) and Buffalo Phils (food delivered by model train with a massive Lego city).

Eau Claire, Wisconsin

As you approach Minneapolis, consider making one final pit stop in Eau Claire. Take in the Sculpture Walk, boasting a collection of over 150 sculptures and recognized as one of the largest in the nation. Additionally, don’t miss the opportunity to explore the riverwalk in Phoenix Park.

For an engaging indoor experience, the Eau Claire Children’s Museum or the newly renovated Public Library are excellent destinations that offer young children ample opportunities to explore and discover.

Frequently Asked Questions about Road Tripping with Kids

1. How can I ensure safety during our Midwest road trips?

Safety should always be your top priority. Make sure all car seats are installed correctly and that seat belts are worn at all times. Plan your route in advance, and consider road conditions and weather forecasts. Keep an updated first-aid kit in the car and be aware of where hospitals or clinics are along your route. Pack your insurance card and know your login so you can check for in-network urgent care clinics should the need arise.

2. What’s the best way to keep kids comfortable during long drives?

Comfort is key on Midwest road trips. Dress kids in loose, comfortable clothing. Bring along pillows for longer drives and plan regular stops to stretch legs and burn off energy.

Also, keeping the car clean and clutter-free can contribute to overall comfort. Easier said than done, I know, but I have a few tips for car organization in this post.

3. How can I maintain a peaceful atmosphere in the car?

Set expectations before you start your journey. Explain the importance of being respectful and patient. Create a playlist of everyone’s favorite songs or listen to audiobooks that the whole family can enjoy. Remember, your attitude sets the tone for the trip.

I ensure each kid that we are doing one thing each day specifically with their interests in mind.

4. How do I keep the kids entertained throughout the trip?

Creativity is your best friend here. Pack travel-friendly games, download movies or shows on tablets, or play classic car games like “I Spy” or “License Plate Game”. I have tons of my favorite road trip activities listed here.

Consider creating a travel journal where they can document their Midwest road trip.

5. Should I pack meals or plan to stop for food?

A mix of both works well. Pack plenty of healthy snacks and drinks to curb hunger between meals and pass the time. For meals, research kid-friendly restaurants along your route. Trying local cuisine can be one of the highlights of Midwest road trips.

6. Are there any recommended apps for road trips? Absolutely! Apps like Roadtrippers and Waze are great for planning your route and getting real-time traffic updates. For entertainment, consider apps like Libby (for e-books and audiobooks) or Netflix and Disney+ (download shows/movies for offline viewing).

7. How often should we take breaks?

For comfort and safety, plan to stop every 2-3 hours. Use these breaks for restroom visits, meals, and to explore attractions along the way. This break-up makes Midwest road trips more manageable for kids. If you have an infant in the car, pediatricians advise not to leave them in their car seat for more than 2 hours at a time at risk of impacting spinal development.

8. What are some essential items to pack for kids? Apart from clothing and toiletries, consider packing items such as blankets, favorite toys, wet wipes, hand sanitizer, sunscreen, hats, and reusable water bottles. Don’t forget chargers for electronic devices!

9. How can I make the trip educational for my kids? Midwest road trips offer ample opportunities for learning. Research each destination beforehand and share interesting facts or play podcasts/Youtube videos about the destination en route. Visit historical sites, museums, and nature reserves. Encourage kids to read road maps or calculate distances.

National Parks and State Parks have ranger and naturalist programs. Inquire when you arrive.

Final thoughts on Midwest Road Trips

The Midwest is packed with family-friendly attractions. Remember, every family is different. Tailor your Midwest road trips to suit your family’s interests and needs. Happy travels!

Midwest Road Trips Family Friendly Pin

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