A Cross Country Holiday Road Trip With A Toddler: Cool, Stupid, or a Little of Both?

I'm going to out-Griswold Clark Griswold, and you're invited along

In 2019, Josh and I did something that was, up to that point, the most ambitious holiday travel plan I’d ever embarked on. We flew from Los Angeles to Minneapolis, and then drove to my hometown, kicked it with my family for a spell, and then flew to his hometown of Pittsburgh on Christmas Day, where we stayed for a couple of days before flying back to Los Angeles. Did I mention we had his 55-lb dog Luca with us the entire time? 

It was hectic, especially thanks to the dog of it all, but thanks to no travel headaches behind the general low-intensity headache that is domestic air travel, we made it through without any disasters. 

We vowed that the next year would be more low-key. And it a fucked up monkey’s paw wish kind of way, I suppose “low-key” describes Christmas of 2020.

In 2021, we had a seven-week-old infant that we were still getting the hang of caring for. I know people travel by plane with tiny babies all the time, but I did not want to be one of them. We stayed home, again. 

This year, we’re doing something that is much more ambitious than even our 2019 Party Aunt and Uncle itinerary. We’ve skipped the last two years of holidays with our families, and who knows what next year will bring. We are going balls to the wall, full-on Clark Griswold in multiple senses of the word. 

We’re loading the aforementioned dog and baby (now almost 14 months old) into my car and driving all the way to Minnesota, and then Pittsburgh, and then back to the West Coast. We can’t fly with the dog anymore due to (understandably) tightened standards on animals on planes. We didn’t want to board him because he’s almost 8 years old and the thought of leaving him in a kennel over the holiday makes me Velveteen Rabbit-levels of sad. Besides, we have always enjoyed going on road trips as a family. And we don’t know how much longer both of us will have the luxury and curse of remote work– one of us can get stuff done while the other one drives, so long as we get flashes of cell service. 

We’ve got things covered back home. Somebody is staying at our house with our cat (who hates road trips) while we’re gone and we live on a very neighborly street and plus we don’t really have anything valuable to steal– Unless, that is, you want to steal our couch, because we’re replacing it soon and ugh the thought of moving the old one out and arranging all the resale logistics bums me out. But I digress.

We’ve done the drive from Los Angeles to Minnesota and back more than once. We’ve driven from LA to MSP to PGH and back once. 

We’ve never done the cross country drive during the winter, and we’ve never done it with a baby. 

I’m starting to worry that this might not have been a great idea. 

I mapped out how much ground we’re covering during the first leg of our trip, and the number of miles we’re driving is dizzying. I don’t even want to type it out here because I’m realizing now that to an outsider this plan might appear to be very stupid.

I don’t want my car to find out what we have planned for her. I’m clicking back and forth between this composition tab and a map tab and I feel the way I felt when I made the mistake of agonizing over the Chicago marathon map in the weeks before I ran it for the first time. Good grief. 

But bad decisions love an audience, and so I’m inviting you all along on the trip, sort of. I’ll be regularly updating what we’ve gotten up to and how the day went. Hopefully this dumb experiment can be instructive to others who may want to load their car full of family and attempt something similar. 

Wish us luck. 

Illustration by Jack Dylan