A Road Trip Through Iowa and its Unexpected Pleasures

When you least expect it, the heartland wraps its arms around you. I never imagined Iowa would make my list of must-see American destinations, but sometimes, family steers you toward the best discoveries. When my son’s future in-laws extended an invitation, I charted a two-week road trip through Iowa. Whether you are road-tripping solo like I did or looking for family fun at every turn, Iowa has surprises tucked into every bend of its byways.

An Unexpected Journey Through Iowa

I am a loop traveler at heart. Whether I am lacing up hiking boots, pedaling along a back road, or steering a rental car, the satisfaction of circling back to the beginning with new memories brings me inspiration. My loop began when I flew into Sioux City and picked up my rental car. I started by driving across the northern portion of the state, then back across the center, stopping in unique towns with timeless traditions.

There is a certain magic to the open road — especially when you have the Midwest’s endless skies stretching out before you and a map full of possibilities. Although my recent Iowa road trip started as a solo journey, I discovered along the way that this state is brimming with family-friendly detours, kid-approved adventures, and moments that could turn any trip into a cherished memory, no matter who is riding shotgun. My route truly began in Orange City, where my son’s future in-laws live, and I proceeded to traverse through charming towns, historic sites, nature escapes, and quirky Americana.

Orange City felt like walking into a storybook. The town’s Dutch heritage spills out onto every corner, from clog-shaped signs and windmills in the park to the annual Tulip Festival held every May — a perfect event for families, especially little ones who will love the colorful costumes and parades.

At the Dutch American Heritage Museum, I wandered through carefully curated rooms that walked me through the immigrant experience, from humble kitchens and handmade clothes to sports, music, and faith. It is an immersive lesson in resilience that would intrigue older kids and adults alike.

From Orange City, I veered toward Okoboji, Iowa’s quintessential lake town. Though I arrived in winter, I quickly learned that the locals embrace all four seasons with flair. The University of Okoboji Winter Games transforms the frozen lake into a wonderland: broomball tournaments, snow softball, human foosball, and even the “drill or die” ice auger races. As a solo traveler, I marveled at the sheer enthusiasm, but families would find this a can’t-miss seasonal festival.

For quieter adventures, ice fishing guides help newcomers and kids safely experience the art of dropping a line through the ice. Summer transforms the area with warm-weather alternatives: jet skiing, paddleboarding, and family picnics at Arnolds Park Amusement Park. The food trucks parked lakeside serve BBQ, melty grilled cheese, and other kid-approved snacks.

I stayed at The Oakwood Inn, which offered a cozy retreat each evening with luxurious touches, a Jacuzzi tub, and breakfasts crafted with genuine care. Meanwhile, a visit to Okoboji Classic Cars was an unexpected favorite, with vintage cars nestled beneath murals that made it feel like stepping into a living 1960s streetscape. Although I am not a “car enthusiast,” the displays here will pique everyone’s interest, even the kids.

Next up: Mason City, a town where art, music, and architecture converge. I checked into the Historic Park Inn, the last remaining Frank Lloyd Wright hotel in the world — a stunning piece of design history that feels like stepping back in time. Families traveling together might opt for a self-guided architecture walk or a visit to the Stockman House.

Daylight brought me to the Music Man Square, where Meredith Willson’s legacy invites visitors to wander through recreated movie sets, explore American music history, and even join a barbershop quartet or two. It is part museum, part nostalgic playground, and offers interactive exhibits that little ones will love. The blend of art, design, and Midwest charm made Mason City feel like a living museum tailor-made for families.

In Decorah, the fresh air is the main attraction. I hiked through Dunning Springs Waterfall and along the 11-mile Trout Run Trail, but this charming town is perfect for families, too. The park at Dunning Springs offers picnic spots, and the waterfall is a favorite for family photos and engagements alike.

Decorah’s outdoor lineup includes kayaking the Upper Iowa River in the summer or snowshoeing the trails at Kettleson Hogsback Wildlife Management Area in the winter. I arrived on a chilly day, so I checked out the town’s boutique-filled downtown and visited the Vesterheim Norwegian-American Museum, which offers kid-friendly activities with exhibits that bring immigrant stories to life in vivid, tangible ways.

Decorah’s B&Bs and Victorian homes take visitors back in time. I thoroughly enjoyed my stay at the B&B on Broadway. Built by Norwegian immigrants in 1910, the home’s lovingly restored charm told stories all its own.

On my way to McGregor, I enjoyed driving through the countryside and naked cornfields. I made a side trip to see the formations referred to as Chimney Stacks, running along the Upper Iowa River. They are best seen from the seat of a kayak. However, when it is too cold to navigate the river, drive to the tiny town of Bluffton and view them from the bridge. The Upper Iowa River is recognized as one of the most beautiful places to kayak in Iowa and the United States as a whole. I drove the back roads, enjoying the countryside and naked cornfields on my way to McGregor.

The road unwinds along the Great River Road toward McGregor, where the Mississippi River whispers stories of steamboat towns and frontier life. The town’s history museum and quirky shops add layers of charm.

The Old West vibe, complete with saloons-turned-inns, offers both historic appeal and hearty hospitality. The Backwoods Bar & Grill serves up pizza and BBQ. I arrived on a day when a young woman and her friends were celebrating a birthday. They invited me to join in the fun, and later, I retired to my period-decorated room upstairs at the Backwoods Bed and Bath.

The Indie shops and galleries scattered along Main Street proved irresistible, offering local crafts, vintage books, and artisan foods to fill my picnic basket for the next day’s adventures on the road.

McGregor’s streets may be quiet in winter, but come summer, the Driftless Region’s dramatic landscapes beckon outdoor enthusiasts to Pikes Peak State Park. There, families can hike to a 500-foot bluff as I did to watch the Mississippi and Wisconsin Rivers collide. Here, I found myself imagining Huck Finn and Tom Sawyer as I explored Pikes Peak State Park’s panoramic overlooks. The local trails offer an excellent excuse for young explorers to burn off road trip energy.

In Dubuque, the National Mississippi River Museum & Aquarium is an interactive treasure trove for visitors of all ages. I spent hours learning about the river’s impact on America’s growth and watching kids delight in the touch tanks, where they could pet baby stingrays.

Dubuque also offers riverboat cruises, bluff-side hikes, and plenty of kid-friendly dining and entertainment, making it an ideal multi-day stop on any family itinerary.

Cedar Rapids was my next stop — a city alive with arts, history, and parks. I wandered through the Grant Wood galleries at the Cedar Rapids Museum of Art, but for families, the true highlight is the Czech and Slovak Museum & Library. The exhibits bring immigration history to life, and nearby, the NewBo City Market serves up artisan eats and space for kids to roam.

Bever Park, another local gem, offers everything from skating and swimming to farm animals, perfect for travelers with little ones looking to stretch their legs. The Cedar Valley Nature Trail invites cyclists, joggers, and strollers alike to soak up Iowa’s scenic countryside. I spent a good hour on the trail looking for wildlife and stopping to listen to the stream rush by.

My last stop on the loop before returning to Sioux City to fly home was in Pella, another Dutch-rooted town that shines in springtime when the tulips bloom. Jaarsma Bakery alone is worth the trip, serving legendary almond pastries known as “letters” — a sweet sendoff.

My solo trip through Iowa was a deep dive into America’s cultural quilt, stitched together by welcoming communities, rich history, and playful stops that appeal to both lone wanderers and families. Whether you are chasing waterfalls in Decorah, digging into Dutch pastries in Pella, or watching the sun set over the Mississippi in McGregor, Iowa offers a slice of Americana perfect for every season and every traveler.

If you are planning your own journey, map your route loosely, leave room for detours, and savor the little surprises along the way. Whether you’re exploring solo or surrounded by kids in the back seat, the heart of Iowa will always make room for more travelers.

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About the Author: Tracy Ellen Beard is a freelance writer, editor, and photographer. Tracy’s writing focuses on luxury and adventure travel, spas, fine dining, wine, outdoor activities, and delicious libations. Her favorite pastimes include hiking, kayaking, meeting new people, and experiencing different cultures worldwide. Tracy shares a unique perspective on the world from her personal journeys and excursions as the founder and past president of an international children’s nonprofit. Her 20-plus years of experience writing in various genres, and her culinary training in San Francisco, California, add to her knowledge and expertise.

Find more from Tracy on her website.