Toddler trippin’: The four stages of dreaming big with toddler vacations

A cross-country trip with a toddler…how hard could it be?

Photo by: ldifranza

Step One: The Idea

“Let’s go to that ginger festival this year,” I said, diving into my pasta as Patrick and I settled down at the dinner table, toddler safely tucked into bed and–knock on wood, crossing fingers, crossing toes–sleeping.

“Sure,” Patrick said amiably. My good old always-up-for-adventure partner. “Where is that?”

“Uh,” I replied, taking a gulp of wine. “Chicago? Yeah, Chicago I think.”

I think Patrick raised an eyebrow in slight skepticism.

“It’d be fun!” I added. “We’ve never been to Chicago. We could see the city, see all the gingers, you know.”

If this were a movie script and not a depiction of something that happened in real life and I had more creative license, I’d have Patrick say here that redheads aren’t things to be ogled at. But in my defense, our daughter is a curly red-haired kid, so we’d be going with her to be part of the red sea.


More pasta, more wine, I’m getting into happy trip-planning mode. I mused about the long drive. “We could take the train,” I suggested. We could eat, walk around, it’d just take a little longer…

Step Two: Denial

After dinner, I grabbed the laptop and looked it up. Great, there’s a train from Richmond to Chicago, I figured there would be but good, good, we’ll just see how long….

“Yikes,” I said, almost choking on the wine I was still nursing. “Um.”

Patrick looked over my shoulder. The estimated trip time to get from DC to Chicago by train was 24 hours and 5 minutes. An entire 24 hours and five minutes. We could get a sleeper car for $705, or seats for less.

“Well…” I said, but Patrick shook his head. We were not going to spend 24 hours and five minutes on a train with a toddler, without even having our own room. Winnie wouldn’t even have her own seat, being under two, because we’re sure not going to pay for an extra one when we have an option to get her in for free.

“How long of a drive is it,” I mused, pulling up a new tab.

Pretty long, turns out. About 12 hours, and that’s not counting stops. I thought back to our trip to North Carolina last summer. True fact: I almost just typed South Carolina because that’s how long our trip to North Carolina took with stops. It’s natural with a kid; you need to change, stretch legs, eat. I need to pee about once an hour, you know. I’m not complaining, so much as facing a reality.

But I wasn’t quite ready to face Chicago reality yet.

We could do it, I thought. Maybe we could make it a two-day road-trip, split it up somehow, then see the city, ogle the gingers slash show off our ginger, eat some pizza, and go home…

Step Three: The Tipping Point

“When’s the festival?” Patrick asked.

I looked it up.

The Redhead Days Chicago page had just announced the dates were approved…for June 4th and 5th.

“That’s kind of soon,” we mused. I quickly tallied other responsibilities we had between now and then. There was a trip to Denver for me, a trip to Baltimore for him, a month of overlapping last rent and the new mortgage on our house…the usual flotsam and jetsam of things planned in the next month or two of a family.

I clicked out of Google Maps. I clicked out of Redhead Days.

“She probably wouldn’t get much out of it this year anyway,” I mused. It’d really just be for us, anyway. Maybe next year…

Step Four: Acceptance

The thing with planning trips with toddlers is that everything takes longer, and they’d probably realistically be just as happy staying home and knocking down block towers all day. Going places is awesome sometimes, but also exhausting, and often plans that we would have made easily on a whim at one point in life now never make it past the Google Maps tab.

But then when we do manage to haul ourselves somewhere, we feel so damn accomplished. I took my daughter with me solo on a plane to Indiana a few months back, and I felt like a BOSS by the time we got home. And during the trip back, I didn’t even have my Tula1 carrier! HORROR.

But it was fine, in the end. And it is slowly getting more fine. Packing a huge diaper bag for outings is becoming more a thing of the past. It’s getting finer and finer. So while we may still shy away from things that sound like they’re more trouble than they’re worth, I also want to remember that feeling when I think about larger trips. It’s a balance. Everything is a balance.

So next year when my little family–knock on wood, cross fingers, cross toes–visits Scotland, remind me of that boss feeling. I hear it’s a bit further away than Chicago…

  1. I am not affiliated with Tula. I just really like them. 
  • error

    Report an error

Hayley DeRoche

Hayley DeRoche is a librarian with a penchant for cardigans and corduroys. Luckily, her professional life revolves more around technology & information than fashion.

There are no reader comments. Add yours.