How to Road Trip With a 2-Year-Old . . . and Actually Enjoy It

The decision to drive instead of fly to New York from Chicago should have been an easy one to make. By the time we would have gotten to the airport, taken off, landed, gotten our car rental, and driven to the Catskills, flying would have only saved us a few hours of travel time and cost about four times as much. Despite all the practical reasons not to fly, the thought of driving 28 hours round-trip with a 2-year-old who isn't used to the car was not a comforting idea.

We don't drive a lot in Chicago, since thankfully we live in a walkable neighborhood and I like the exercise. The longest my son is in the car is the 20-30 minutes it takes to get to the aquarium or museum. So naturally, I needed to find a way to keep him happy in his car seat for much longer, unless I wanted it to be a miserable drive. Thankfully, with a lot of planning and a little good-natured luck, not only was my long road trip with my 2-year-old a success, but I actually enjoyed getting to see the country with him.

  1. Know your route. There are a lot of times where the free-spirited nature of a road trip can be invigorating and part of the adventure. I'm not saying to be inflexible as to how you get there, but it will help immensely if you know how you want to get where you're going. This will allow you to plan for interesting, scenic, engaging activities along the way. Even the best toddlers — and adults, for that matter — need to get out and stretch their legs every so often. Map out potential playgrounds and rest stops, and check ahead of time to make sure everything is still open when you want to stop. I didn't do the latter, and one of our planned rest stops was closed due to construction, with the next one another 25 miles away. When you have to pee and your toddler wants to run, those extra 25 miles can seem like forever.
  2. Get your kid hyped, not hyper. Having a planned route means you can talk up the rest stops. Plan a small activity at each stop that you can get them excited about during the drive. Whether it's eating a sandwich, buying a new toy, seeing the world's biggest ball of yarn, or setting up a small obstacle course, your kid will be excited for the next leg of the drive. When we were approaching the hotel that we were staying at along the route, I started telling my son about this amazing pool we were going to go in. As soon as we got there, the swim diaper was on and he was splashing away while my husband unpacked the car. He had something to look forward to, and he understood that the end was almost near.
  3. Stick to your schedule as best as you can. I'm a bit obsessive about sleep, and even though we normally do not let him sleep in the car, while road tripping, I had to be more flexible. Just before his usual naptime, we made a quick stop so he could stretch his legs and get a fresh diaper, and once we were back in the car, the electronics and toys had already been hidden and replaced with his blanket and lovey. Believe me, after listening to kids' songs, obnoxious toys, and TV shows for hours, a little bit of quiet time will do everyone some good.
  4. Hide all electronics until absolutely necessary. I screwed up this one. Being the occasionally Type A person that I am, I wanted to get the car ready the night before we embarked. This meant that I had hooked up the charged iPad into our brand-new backseat car organizer and filled all the storage cubbies with new toys and games. It didn't even take him two seconds in his car seat to see the iPad, also known as the way he gets to watch Thomas and Sesame Street, and, using his best whiny-toddler voice, demanded for it to be turned on. I had planned to not bust out that bad boy for at least a couple of hours, but no such luck. Had it been hidden, I may have gotten a few hours free from the weird morality of Thomas and Friends.
  1. Download, charge, and always have a backup. Netflix and Amazon really have parents' backs with their downloading options. Favorite TV shows and movies can be stored onto your devices and enjoyed without stripping you of all your data. If your car doesn't have a way to charge electronics, I'd recommend going with a portable charger just in case. The last hour of our road trip to the Catskills was unsurprisingly without service, and our iPad had crashed. If it hadn't been for my husband's ability to talk about all the cool things we were going to see once we got there and my secret stash of toys, it would have been a rough last leg.
  2. Have Mama's present bag. Like most toddlers, my son loves little cars and trucks, books, and crayons. A couple days before our journey, I went to the store and bought 20 bucks' worth of small toys that were then individually wrapped. If I felt like things were getting rough, out came the magic bag of presents, where he got to pick a new toy. From the choosing to the unwrapping, playing, and tossing aside, it bought us at least an hour of happy distraction.
  3. Make things easy to grab. Since we only have one kid, we were able to use the rest of the back seat for storage of snacks, toys, diapers, and spare clothes. However, what didn't work was that we stuffed everything in one gigantic tote bag, which quickly became a jumbled and unusable mess. For my next road trip, I plan on buying a plastic container with smaller drawer organizers inside and placing that on the seat. If you're driving by yourself, place a container on the front seat for you to have easy access. Have a couple gallons of extra water in an easy-to-pour location so bottles can be refilled without stopping.
  4. Be aware of all things pee. My son is not potty trained yet, so I figured that driving with him in diapers would be kind of amazing. Except that sitting in one position for such a long time meant that his normal ability to go a few hours had dwindled down to two. Placing a booster pad in his diaper helped the dryness a lot and allowed us to stretch him farther than we could have otherwise. If your toddler is potty trained, now is not the time to forget your portable potty. Bringing it will help mitigate the risk of accidents because the lines at some rest stops are way too long, and holding it is hard.
  5. Take a lot of photos. Vacation photos are some of my favorites. Not only do they capture you at some of your most excited, exhausted, and memorable times, but I also find that they help ease any bad moments that might have happened. No road trip is going to be perfect. You'll probably snap at your partner at least once and your toddler might cry, but looking at the photos at the end of the day, and even months later, might help encourage you to do it all again. Plus, you can't embarrass your toddler later in life with awkward family vacation photos if you don't have them.