Ultimate Midwest Road trip
A Family-Friendly Midwestern Road Trip
Who doesn’t love a good road trip with the family? I remember growing up traveling with my family, stopping at parks on our way to our destination to play and eat my grandmothers famous sub sandwiches and pasta salad. Core memories were made on the roads of the Midwest. Just think of the funny stories, enjoyable moments, and memories that are created as you travel through the roads exploring the beauty surrounding you. America’s Heartland is full of charming and quaint towns with a perfect backdrop of beautiful natural landscapes for a family photo. History buffs, outdoor enthusiasts, and foodies alike can come together and use this road map to guide you to the Ultimate Family Road Trip.
If you are anything like me, having a visual of where you are going. Here is a Google Map of the road trip you and your family could embark on. Whether it is a family as big as ours or just you and your spouse, an ultimate Midwest Road trip like this is enjoyed by all.
Day 1-2: Chicago, Illinois
Kick off your adventure in the Windy City. Chicago offers a blend of iconic attractions and cultural experiences. Start with:
The Art Institute of Chicago: Home to masterpieces like Grant Wood’s American Gothic and Van Gogh’s The Bedroom.
Millennium Park: Snap a selfie at Cloud Gate (The Bean) and stroll through the lush Lurie Garden.
Deep-Dish Pizza: Visit Lou Malnati’s or Giordano’s for a slice of Chicago’s famous pizza.
Wrap up your visit with a sunset architectural river cruise for stunning views of the skyline!
Day 3: Milwaukee, Wisconsin
Drive north along Lake Michigan to Milwaukee, a city known for its beer and lakefront charm. Check out Bradford Beach for some fun in the sun as well!
Harley-Davidson Museum: Explore the history of this iconic motorcycle brand.
Milwaukee Public Market: Sample local flavors like cheese curds and bratwurst.
Lakefront Brewery: Take a quirky brewery tour and enjoy craft beer with a side of humor.
Day 4 & 5: Door County, Wisconsin
Continue north to Door County, often referred to as the “Cape Cod of the Midwest. It is really such a beautiful part of the country, especially driving in the fall with the colors of the trees. Quite the remarkable backdrop.
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Peninsula State Park: Go hiking, biking, or kayaking with stunning views of Green Bay.
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Fish Boil Dinner: Experience this local tradition at places like White Gull Inn.
Charming Villages: Stroll through Ephraim and Sister Bay, filled with boutique shops and art galleries. Find a hotel in Sister Bay
Day 6: Minneapolis-St. Paul, Minnesota
Head west to the Twin Cities for a mix of urban culture and natural beauty. There really is so much to do in Minneapolis, it was difficult to only put 1 day for this trip.
Minnehaha Falls: A picturesque waterfall located within city limits.
Mall of America: Shop, dine, or enjoy the indoor amusement park.
Walker Art Center and Sculpture Garden: Home of the famous Spoonbridge and Cherry sculpture.
Day 7: Badlands National Park, South Dakota
Shift gears to explore the rugged beauty of the Badlands. Outdoor enthusiasts will have a blast with the amount of trails and outdoor activities that are had at the Badlands.
Scenic Byway: Drive through stunning landscapes of layered rock formations.
Hiking Trails: Take a short hike like the Door Trail or Notch Trail for incredible views.
Wall Drug Store: Stop at this kitschy roadside attraction for souvenirs and homemade donuts.
Day 8-9: Black Hills and Mount Rushmore, South Dakota
No Midwest Road trip is complete without visiting these iconic landmarks. It may feel out of the way but will be well worth it visiting a few iconic landmarks in the United States.
Mount Rushmore National Memorial: Marvel at the monumental carvings of four U.S. presidents.
Custer State Park: Spot wildlife like bison and elk on the Wildlife Loop Road.
Crazy Horse Memorial: Learn about Native American history and culture at this massive sculpture in progress!
Day 10: Omaha, Nebraska
As you head back east, stop in Omaha for a dose of Midwestern hospitality. Do not leave Omaha without visiting Henry Doorly Zoo and Aquarium. Taking a summer trip? Stop and check out the College Baseball World Series!
Old Market District: Explore cobblestone streets lined with shops, galleries, and restaurants.
Henry Doorly Zoo and Aquarium: A world-class zoo featuring an indoor rainforest and desert dome.
Steaks: Indulge in a perfectly cooked Nebraska steak at a local steakhouse.
Tips for the Perfect Road Trip
Pack Smart: Include essentials like a first aid kit, snacks, and a reliable GPS. Check out this one here!
Be Flexible: Allow time for unexpected detours and hidden gems.
Plan Accommodations: Book in advance, especially during peak travel seasons.
Stay Connected: Download offline maps and playlists for long stretches of road.
The Midwest is more than just flyover country; it’s a region brimming with charm, history, and adventure. This road trip itinerary highlights the best of the Midwest while leaving room for you to explore its countless surprises. So, pack your bags, grab your keys, and hit the road for a journey you’ll never forget!
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