A Midwest Road Trip- Hit 4 States with this easy Route!
I have driven across the country twice, and somehow both times I completely skipped the middle. Visiting all 50 states has always been a goal of mine, so when the Women in Travel Summit was held in Kansas City, it felt like the perfect opportunity to finally plan a Midwest road trip.
After researching the highlights of the region, I mapped out a simple Midwest road trip itinerary that would cover four states in less than a week. Missouri, Kansas, Nebraska, and Iowa are surprisingly close together, and the longest drive we had was just three hours.
Midwest Road Trip Itinerary: 4 States in 6 Days
This Midwest road trip is ideal for families or anyone looking for an easy, manageable route. With short drive times, fun cities, and unique stops along the way, it is a great introduction to this part of the country.
Midwest Road Trip Map

First Stop: Kansas
From Boston, it was about a 2.5 hour flight into Kansas City International Airport. After a quick shuttle ride to pick up our rental car, we officially kicked off our Midwest road trip.
One thing that can be confusing is that Kansas City actually spans two states. The airport is located in Missouri, but within minutes you can cross into Kansas.
Our first stop was Kansas City, Kansas for one very important reason… BBQ.
We went straight to Joe’s BBQ, a local favorite located inside a retro gas station. The line out the door tells you everything you need to know. The must-order item is the Z-Man Sandwich, made with slow-smoked brisket, provolone cheese, crispy onion rings, and a toasted Kaiser roll. It completely lived up to the hype.
If you have extra time in Kansas, head to Prairiefire in nearby Overland Park. This area combines shopping, museums, and a scenic wetlands trail, making it a great stop for families.
After lunch, we made our way back to Kansas City, Missouri where we spent the next two days exploring.







Next Stop: Nebraska
The next leg of our Midwest road trip took us about three hours north to Omaha, Nebraska.
This ended up being my favorite stop of the trip. Omaha is clean, easy to navigate, and packed with family-friendly activities. You could easily spend two to three days here.
The biggest highlight is the Henry Doorly Zoo, which is often ranked among the best zoos in the country. If you plan to visit, set aside an entire day because there is so much to see.
One of the most unique experiences in Omaha is walking across the Bob Kerrey Pedestrian Bridge. Halfway across, you can stand with one foot in Nebraska and the other in Iowa. The kids loved “bobbing” back and forth between states.





Next Stop: Iowa
After spending a few days in Omaha, we continued our Midwest road trip east to Winterset, Iowa.
Winterset is best known for the Bridges of Madison County. There are six covered bridges remaining, and exploring them feels like stepping back in time. Only one of the bridges is open to vehicles, but all are worth visiting.
We spent the day driving through the countryside, stopping at each bridge and taking in the peaceful scenery. It is a slower pace here, which made it a nice contrast to the city stops earlier in the trip.
Winterset is a small town, so one night was the perfect amount of time before heading back.






Wrapping Up the Midwest Road Trip
From Winterset, it was just under a three hour drive back to Kansas City International Airport for our flight home. In six days, we visited four states without ever feeling rushed.
Going into this Midwest road trip, I will admit my expectations were low. I ended up being completely surprised by how much there was to see and do.
What stood out the most was the people. Everyone we met was genuinely kind and welcoming. Coming from the Boston area, it took a minute to adjust, but I quickly adjusted to the kindness.
A Midwest Road Trip with Kids
One of my favorite traditions is taking a solo trip with each of my kids. On this particular Midwest road trip, Harry was my travel buddy.
Last year, Andrew’s trip was to Paris. Harry went to Kansas. When I tell people that, they burst into uncontrollable laughter. Harry is always confused about this and finally asked me “Is Paris really nice or something?”
His confusion comes from how much he loved the Midwest, making it hard for him to imagine anything better.
I already ordered the Snapfish album from our trip, which is another tradition of ours. He flips through it every night before bed. Those memories will last a lifetime.
Tips for Planning a Midwest Road Trip
- Keep your route simple since the states are close together
- Plan for short driving days to avoid burnout
- Spend extra time in Omaha if traveling with kids
- Try local BBQ in Kansas City, it is a must
- Allow time for scenic stops like the Bridges of Madison County
If a Midwest road trip is not already on your bucket list, it should be. It is easy, affordable, and filled with unexpected highlights that make for an unforgettable family adventure.
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