8 States in 7 Days: The Great Plains Road Trip that Replaced Our Cancelled Cruise

At the beginning of 2020, I had five trips planned for the year.

Even as a single mom traveling alone with my kids, I’ve always been ambitious about travel. I have this slightly delusional — but deeply sincere — goal of getting to all 50 states before they’re fully grown. I know how quickly the years pass, and I don’t want to look up one day and realize I waited for the “right time.” We haven’t hit all 50 yet, and the map still has gaps. But we built the habit of going early on — and we’re not done.

One of those five trips was a Caribbean cruise with my parents, my brother, and his kids. It was the first time in years all of us would have traveled together. We were genuinely excited. It would have been the kids’ first cruise — and a chance for them to hang out with cousins and grandparents beyond the typical overnight sleepover.

And then, like everything else that year, it disappeared.

As lockdowns stretched from weeks into months, we found ourselves at home — restless, disappointed, and more than a little stir-crazy. The cruise wasn’t just cancelled; it represented something we had been looking forward to during a season that suddenly felt uncertain in every way.

I could accept that we weren’t going to the Caribbean. What I couldn’t accept was losing the entire summer.

So I did what I always do when I start thinking about travel. I pulled out a map.

The “BORING STATES” PLAN

I announced to the kids that instead of the cruise, we were going on a week-long road trip. And not just any road trip. We were going to “knock out the boring states.”

You know the ones. The ones no one brags about visiting. The ones people assume are just flyover country. The states you usually drive through on your way to somewhere else. I didn’t fully know what we would do there. But I was determined to make it fun.

For weeks leading up to the trip, we joked that it might be boring. Maybe there would be nothing to do, and it would probably be wildly uneventful. But at least we wouldn’t be stuck at home.

The more I researched, however, the more I realized how wrong I had been. I found outdoor amphitheaters carved into hillsides, national parks with dramatic, otherworldly landscapes, historic hotels, quirky roadside attractions, and layers of American history I had only half remembered from childhood road trips with my own parents.

This wasn’t going to be a consolation trip. It was going to be an adventure.

THE NIGHT BEFORE WE LEFT

The night before we were supposed to leave, around 8 p.m., I ran out to Target for the final round of road trip supplies — snacks, toiletries, the usual last-minute things.

Two miles from home, my car broke down.

If you’ve ever planned a road trip, you know departure windows matter — especially when you’re covering a lot of ground. We were supposed to leave at 6 a.m. the next morning. I don’t tend to build in excessive margin. I build in optimism, and a willingness to adjust when things shift.

By morning, my mechanic confirmed what I already suspected: it wasn’t minor. It was significant. And because this was mid-2020, parts would take at least two weeks to arrive. We were delayed before we even started.

Sitting in my mechanic’s lobby, I opened my laptop and searched for rental cars. Options were limited and availability was sparse. The only affordable vehicle left was a minivan — a category I had confidently declared I would never drive. And yet, by 10 a.m. that day, we were loading our bags into that minivan and pulling out of town.

As it turns out, sliding doors, ample cupholders, and generous cargo space are not so bad after all.

ON THE ROAD

By late morning, we were officially on the highway — hours later than planned, but moving. There’s something fresh and exciting about the first stretch of a road trip. The snacks are still organized. The car smells new. The kids are cooperative. No one is tired yet.

We crossed through Illinois, but not the version we’re used to. We’ve done Chicago plenty of times. This was countryside — long stretches of farmland, quiet towns, and open sky. By the time we reached Dubuque, Iowa, and stood at the edge of the Mississippi River, it felt official. We were finally on “vacation.”

We made a quick stop at the Fenelon Place Elevator — a tiny, steep rail lift that climbs the side of a bluff. It’s quirky and short and exactly the kind of roadside stop that makes kids feel like something unusual is happening. Not everything has to be monumental to be memorable.

That first night, we stayed at a hotel in Prairie du Chien, Wisconsin, with a small indoor waterpark. It wasn’t glamorous. It wasn’t historic. But it was strategic. After a long driving day, letting the kids burn off energy in a pool is sometimes more valuable than a view.

That kind of balance became the theme of the week.

MINNESOTA: A RESET BEFORE THE PUSH

The next day was intentionally lighter. We spent a few hours at the Mall of America — something I had always wanted to see when I was younger but never quite made happen on my own childhood trips. Walking through it with my daughter felt beautifully full-circle.

We didn’t try to conquer it. We chose a few stores, grabbed lunch, and left while everyone was still in a good mood. That was deliberate. The heavier driving days were ahead of us, and pacing mattered more than squeezing in everything.

The following morning, we headed north to Brainerd to see Paul Bunyan. It was slightly out of the way, technically unnecessary — and completely worth it. The kids were a little unsure at first, but they posed for pictures anyway. That’s road trip tradition.

From there, we pointed the car west.

NORTH DAKOTA: THE SURPRISE OF THE TRIP

By late afternoon, we had crossed into North Dakota and stopped to see Salem Sue — the world’s largest Holstein cow — perched above the prairie like a monument to roadside Americana. It was ridiculous in the best possible way.

And then we arrived in Medora. If this trip had a turning point, it was that evening.

We checked into the Rough Riders Hotel, a historic property in the center of town that nods to Theodore Roosevelt’s time in the region. It felt like stepping into a different era — wood accents, photographs, subtle reminders that this wasn’t just another overnight stop.

That evening, we walked to the Pitchfork Fondue. Steak cooked on actual pitchforks, lowered into vats of hot oil, served outdoors overlooking the Badlands. It sounds gimmicky until you’re standing there watching it happen.

Then we made our way to the Medora Musical — an outdoor production carved into the hillside. Musicians. Fiddles. Dancers. Fireworks at the end.

It was cinematic and truly magical. I would go back to North Dakota just to attend the Medora Musical again.

North Dakota wasn’t a filler state. It was the moment — and it was surprisingly beautiful.

The next morning, we explored Theodore Roosevelt National Park. That’s where the prairie dogs stole the show. It was the kids’ first time seeing them up close. Entire colonies popping in and out of the ground, chirping, darting, standing upright. The kids were obsessed. We lingered longer than I expected, just watching them move in and out of their little tunnels.

Later in the morning, we decided to lean into the Western experience and booked a horseback ride through the Medora trails. It was scenic. Quiet. Expansive.

My daughter was not impressed.

She tolerated it more than enjoyed it, and by the end she had firmly decided that horseback riding was not her thing. Wes, on the other hand, had a great time. That’s road trip reality — not every activity lands equally for every kid.

SOUTH DAKOTA: ICONS, WILDLIFE, AND A HAUNTED HOTEL

We crossed into South Dakota that evening and made our way to Mount Rushmore just after dark. I’m glad we went at night. It felt more dramatic somehow — the faces lit up against the sky instead of blending into it.

The following morning, we decided to extend our stay in Rapid City. We had arrived late the night before and checked into Hotel Alex Johnson, a historic downtown property..

When my son and I went down to the lobby to ask about staying another night, we noticed something we had completely missed the previous night: an entire display about the hotel’s haunted history. Apparently, it’s considered one of the most haunted hotels in South Dakota. At that stage of life, my daughter was deeply afraid of ghosts. She had insisted on taking the separate bedroom in our suite the night before — which my son had graciously allowed her to have. We extended our stay. We said nothing. We did not mention the ghost stories until we were driving out of town the next day. She was not amused.

But staying that extra night changed the pace of the trip in the best way. Instead of rushing out early and trying to cram everything into one long day, we had room to ease into it. We could take our time the next morning. That space is what allowed Custer State Park to feel less like a stop and more like an experience. And Custer might have been one of our favorite days of the entire trip.

In one stretch, wild burros walked straight up to our car. You can actually get out and feed them carrots — something that feels almost unbelievable until you’re standing there holding one.

In another section, massive bison roamed close enough to remind you that this is still wild land.

The contrast was surreal. Feed one animal. Absolutely do not approach the other.

We stopped for pie. We always stop for pie.

We detoured to Devils Tower in Wyoming because we were close enough and because some landmarks are worth the extra miles. Standing at its base with my kids felt strangely familiar — I had been there as a child with my own parents.

Later, we wandered through Deadwood’s Main Street and ended up at Mustang Sally’s for dinner.

Nothing about the day felt rushed. That was the point.

BADLANDS AND THE LONG DRIVE HOME

Badlands National Park looked like another planet. Layered rock formations in muted tones, carved by time and weather into something both harsh and beautiful.

We drove the scenic route, stopped at overlooks, and let the kids climb carefully where permitted. There’s a stillness there that feels different from the energy of Custer.

Wall Drug was kitschy and crowded and exactly what you expect it to be. The Corn Palace in Mitchell was quick and quirky — another box checked, but in the best way.

By the time we reached Nebraska and then Iowa again, we had logged nearly 2,800 miles.

We stopped in the Amana Colonies — small shops, historic buildings, and one final meal before turning home.

It wasn’t the Caribbean — and it didn’t have to be.

IF YOU’RE CONSIDERING THIS LOOP

Over the years, I’ve had so many people ask how I plan these trips — especially the less obvious stops, the pacing decisions, and the hotel choices that make the week feel manageable instead of overwhelming.

So I turned this exact 7-day route into a structured itinerary with:

• Where to stay (and when to choose experience hotels)
• Wildlife stops and lesser-known highlights
• Drive sequencing and pacing notes
• Optional detours
• An interactive route map

If you want to skip the research and use the framework we followed — including stops highlighted here and many more — you can find my full Great Plains 7-Day Itinerary here.