The only thing more fun to me than taking a big cross-country road trip… is planning a big cross-country road trip! If done effectively, the planning should take about 3,000 times as long as the actual trip itself. Once you’re out there on the road, you want to be optimizing your precious time and not sitting there wondering what to do, where to go, what to see, and where to eat. Now I’m not going to out on the road with a detailed step by step itinerary. I simply want to be fully aware of what all is out there so I don’t miss anything worthwhile. When I drove from Austin to South Dakota with John two years ago, I researched literally every single town between the start and end points; that way, if I time permitted and/or we were in the mood, we could stop off for a bite at a famous diner, or pose for photos at a big roadside statue, or take a quick tour of a presidential birthplace. We were not adhering to a strict schedule or anything, but we knew what options there were at any given time and place.

So, after the 2018 Black Hills trip, the aforementioned 2019 14-state extravaganza, and the March 2021 Gulf Shores trip, it’s back to the road in August. The Poulters are doing another Galena, Illinois reunion, and rather than us just flying in and out of Chicago, we decided to turn this into a whole thing leading up to the first day of the 21-22 school year.

Our plan involves me doing the first leg of the trip alone—driving from Austin to Chicago, likely with a couple overnight stops in there. Why? Well, we want to have the van, carseats, extra luggage space and whatnot for the trip, but the kids aren’t going to like riding for 20 hours through Arkansas and Missouri and Illinois. But guess who does like that sorta thing… yours truly. Going solo, I can stop at will at every piddly little roadside attraction, state border sign, and historical marker without annoying anyone. If a friend or someone really wanted to, I would welcome a companion to fly into Austin, ride that leg of the trip with me, and then fly home out of O’Hare. But I’m happy to do it solo as well.

In Chicago, I can pick up Lauren and the kids who have booked a one-way flight, and drive us all out to Galena. After that is over, I’ll drive us up to Minneapolis and drop Lauren at the airport so she can return home and have a luxurious week all to herself! I could only dream of such a thing. We might spend a night catching up with old friends in MN and then head out to the Glanzer farm so the kids can have some cousin time for a few days.

When it’s time to go home, the kids and I will make the long drive south back to Austin. I have attempted to talk a family member or two into riding back with us to help keep the kids entertained, and they can fly back to SD when we arrive in Austin. And then the next day John starts 2nd Grade.

Such a journey could look something like this…

Not saying it will happen just like this, but… I could see MLB games in St Louis, Chicago, Minneapolis, and Kansas City along the way, depending on the exact routes.