Maybe you remember this phase of teenagedom, but for a while, we used to laugh and say, “Pics or it didn’t happen.” This was the era of posting 945 photos on Facebook from one night out and it was half blurry, candid digital camera images and half various groups holding skinny arm poses. Then of course, came Instagram, and “doing it for the ‘gram.”

Alllllll the blurry jumping pics, circa 2010.
I think in some ways, social media = the internet = culture since pretty much 2005. Sean Monahan neatly lays out the eras of the Internet in this post, and Anne Helen Petersen does something similar in this phenomenal post. Both of these made me feel seen and made me think about how the internet leaks into every aspect of real life, too.
Because for millennials, social media is culture, it’s not surprising that this kind of ethos shaped how I do everything, including travel. For years I’d chase “the best” of everything, conflating it with what was the “correct” way to visit a given destination. I mean, I worked at Tripadvisor—that was our whole mission! But it also means I have lined up for viral cupcakes and donuts and cronuts and cookies. I booked an Airbnb in Portugal solely off the fact that it had a rooftop with a gorgeous view of Lisbon’s iconic Alfama district, so we wouldn’t have to compete for photos.
The point is, even though I don’t do those things anymore because I have learned that chasing aesthetics isn’t the same as chasing experience,1 I think social media has conditioned us to believe that you can and should get the “best” of everything when you travel. A toddler just blows that right up.
With a toddler, you can’t chase “the best.” But you can chase “the best for your family.”
Roadtrips aren’t always aesthetic, but they are very doable with a toddler.
Some babies scream the entire time they’re in the car, and I feel very, very lucky that wasn’t us at the beginning. Still, there’s so much *stuff* to cram in your car at the beginning that it can feel daunting to try to go somewhere at all, even if it’s via car. But roadtrips opened up travel for us as we got started. I know plenty of people just rip the band-aid off and take a cross-country flight with a newborn but that just wasn’t me. When we started out, we scaffolded our trips like this:
- 30 min drive to my parents to stay overnight
- 1.5 hour drive to grandparents for an overnight
- 2 hour drive to in-laws for 2 days
- 3 hour drive to grandparents for 3 days
- 2 hour drive staying in a condo for 5 days
The roadtrip gear that makes it a little easier.
I still bring way, way too much stuff on roadtrips, mostly because we can, but also because I’d rather just have it than not have it, and yes, I have an SUV. Here’s what we always have in the car:
- I started with the UPPABaby stroller (the Suburban of strollers, truly) and the matching carseat and now we have this massive car seat that holds my 99th percentile toddler and this foldable travel stroller instead.
- This mirror kept me from turning my whole head around—we used it until we switched to forward-facing.
- Car A/Cs are just not meant for carseats. This fan has helped get some of the cooler air back to my toddler.
- A portable high chair makes going to any restaurant easier.
- For babies, we used the same crinkle toys we always played with, plus this fun thing-y.
- For toddlers, this writing tablet always stays in the car, and so do a selection of interactive books like this one (we’re in a big Encanto phase at the moment.), plus these spinners which we STILL play with years later.
- SNACKS, ALL THE SNACKS. And I keep them up front instead of packing them away!
Now, we follow a single rule whenever we roadtrip, which is most often to visit family.
The roadtrip rule I always follow…
2 hours of driving, 1 hour stop. Repeat.
There is no “pushing it.” There is no, “well maybe we can…” What we have learned is the max for us is 2 hours of driving, but ideally it’s 1.5 hours. We time these legs either with a nap/quiet time (which has changed over time) if we can.
For example, I just got back from a trip to Maine (a 3 hour drive, so very doable.) I drove 2 hours to Portland, played at a Deering Oaks Park playground for ~2 hours, and then drove the final hour during naptime around 1 PM. Not me trying to stay awake during that windy drive to some very mellow cello music!
The only exception to this roadtrip rule for me is that sometimes I make a bedtime run if I really have to, or if it’s not a destination I can make easy stops for, or if it’s the type of highway or traffic-y driving that makes timing impossible. Then, I’ll do our full bathtime and bedtime routine and hope we get some shut-eye at some point.
Sample Toddler-Friendly Roadtrip Itineraries
Two of my all-time favorite roadtrips are up in northern New England. First, Acadia National Park in Maine from Boston:
- Drive 1.5 hours to Portland, ME: Grab salads at LB Kitchen or sandwiches from Forage Market and then stop at East Promenade Playground. (There’s also food trucks and a beach at the park right there.)
- OPTION 1: Drive the “long way” up Rt. 1, stopping in Camden for sandwiches at Camden Deli and an easy hike up Mt. Battie Trailhead. (If you must have the “best”, pick up lobster rolls ahead of time at Red’s or McLoon’s, both on the way…another example of “best” vs. “what’s best for your family.”)
- OPTION 2: Drive the “short way” on 95, stopping in Waterville for wiggles out at North Street Playground, across from Dairy Cone. (If you need real food, stop in town instead for burgers at Mainely’s and then you can wiggles out along the riverfront.) It takes another
- It takes another 1.5 hours to get to Bar Harbor from there.
Second, a trip around the White Mountains of New Hampshire, also from Boston (I’m sorry readers from other places, I’ve only roadtripped from my own house!)

- Drive 1.5 hours to Lincoln, NH and stay overnight. Don’t sleep on the Loon Gondola to get you up high without needing to hike with little legs! But there’s also great easy hikes around here: Flume Gorge, Franconia Waterfall, and Discovery Trail were the best with toddlers that want to hike with you. Don’t miss breakfast at nearby Polly’s Pancakes. (Though get there right when it opens, it’s a well-known spot.)
- Then, take the scenic Kancamagus Highway to North Conway and stop at Sabbaday Falls on the way for little hikers or if you’re carrying, Mt. Osceola is the easiest 4000’ and my toddler’s very first in the pack. North Conway gets you close enough to Mt. Washington to do the Cog Railway but you are also close to Storyland (it closes in the fall so check times). It’s a great home base for a few days.
- If you’d like to stay overnight in one more place, Crawford Notch is actually my favorite spot in the Whites. It’s 30 minutes to stay at AMC’s Highland Center. From there, you can do several toddler-friendly hikes (Red Bench Trail, Mt. Willard, and Willey House Dam Loop) and/or pick up the scenic railroad, which my train-obsessed toddler loved watching.
Thanks for being here.

Am I immune to “the best” mentality even after having a toddler? Absolutely not. On a recent (childfree!) roadtrip to my friend’s wedding in New Jersey, we immediately found an iconic deli that had been featured on several t.v. shows that was only 30 minutes out of the way for lunch.
Cut to me at the Vince Lombardi rest stop after an extra hour of unanticipated traffic, crushing a Shake Shack chicken sandwich instead. I wanted to have a Big Travel Moment but what I got was lots of laughs, an uninterrupted nerdy podcast on the history of Nintendo, and a chance to stand up for a few minutes before diving back into gnarly Jersey traffic, which I promptly forgot about as soon as I got on the dance floor later that weekend. We got there, and that’s what mattered.
To getting there,
Kayla
If you liked this post, please consider supporting my work. I’m just a mom in the thick of the toddler years trying to create core memories for our whole family while minimizing meltdowns—I sincerely hope this helps you do the same.
This post was originally published on Travel with Toddlers. Subscribe for more real-talk travel advice, toddler-friendly itineraries, and tried-and-true gear recommendations.
More from FamilyVacationist:
- 8 family roadtrips you haven’t tried yet (but should)
- An epic family roadtrip guide to the Grand Canyon
- 10 unforgettable RV roadtrips for the whole family








