A road trip involves diligent planning and a flexible mindset. It also involves a change in perspective. No longer does the vacation start when you arrive at your final destination; instead, it begins the moment you shift your car into reverse and leave your driveway. A road trip vacation is all the moments between here, there, and in between. Different from a traditional vacation where the destination is the point, the road trip itself is the point. With careful planning and a commitment to flexibility, which may seem like a juxtaposition, road trips can be a new favorite option and offer so many different ways to experience the country.
My family and I drove from Indianapolis to Osterville, Massachusetts, the summer that our daughter turned two. Osterville is located on the southwest side of Cape Cod, the peninsula of Massachusetts that juts off into the Atlantic Ocean, and is most famous for the Kennedys, hydrangeas, being the ferry point for both Martha’s Vineyard and Nantucket, and lastly, Provincetown, located on the very eastern tip of the Cape, where the Pilgrims arrived in 1620. Osterville is also very far from Indianapolis, about 16 hours and 1,000 miles away. We had a CR-V (still have, love Honda and their long-lasting cars!), a 4 ½ year-old, a 23-month-old, and a destination. We also had one of the best times of our lives.
Our perspective for this road trip centered around flexibility. We had a destination we were going to reach and a general time frame by which we were going to reach it. But really, those two parameters were the only solid plans. Everything else, for the sake of our happiness and, at times, sanity, was on a “to be determined” basis. Here is how it worked:
My kids are used to being in the car for two to three-hour stretches due to the fact that my husband and I are the only members of our families who moved away from where we grew up; therefore, meaning that for every birthday, holiday, or visit to grandparents, we get all loaded up and head north. Using this, we broke our sixteen-hour trip up into basically 2-3-hour increments. Our itinerary thus looked like: Indianapolis to Columbus, Ohio. Columbus to Pittsburgh, Pennsylvania. Pittsburgh to Harrisburg, Pennsylvania. Spend the night. Harrisburg to Philadelphia, Pennsylvania. Philly to New York City. NYC to Providence, Rhode Island. Spend the night. Providence to Osterville. Two days in the car, eight states crossed.
To keep the trip fun for the kids, we planned ahead so that every stop was a park we could visit that was unique to what Indy had to offer, with a special emphasis on splash pads since it was July. We ended up having to revise this plan because, well, it stormed our entire first travel day until we got to Pittsburgh. So, what we decided was to look for malls, especially malls that had little indoor play areas. Malls were a saving grace on our road trip, and we ended up stopping at one in Columbus as well as the King of Prussia Mall outside of Philly, which is the third-largest mall in America. The kids loved being able to stretch their legs, have their choice from the food court, and generally escape from the confines of their car seats and play (a major favorite was trying out all the tents inside recreational stores). The parks that we stopped at were incredible, too. We played a life-size version of “Chutes and Ladders” in Harrisburg with giant spinners and slides. We found a kid-sized two-story town in Cleveland, a blue concrete patch that the kids could slide down using cardboard in Pittsburgh. It was such a unique way to see new places as we traveled.
On our way out, we did not stick to our itinerary. For one, it was exhausting. The kids got to play and then sleep in the car. They enjoyed resting while watching movies, they had their books and their toys, and they generally had a peaceful time back there. In the front seat: we got to drive (and by we, I mean my husband…). Because of our flexible perspective, however, this was ok.
On the first night, we decided to stop between Pittsburgh and Harrisburg at a city called Bedford (historically, where Washington stayed during the Whiskey Rebellion. I feel like I need to do a sidebar here and say that I teach ACP US History, so this trip had many thrilling elements for me that for others would be less than interesting. We used the Hilton app to just find a hotel with a pool and free breakfast. This is how we traveled both on our journey out and on our journey back. The kids loved swimming, and we loved how they absolutely conked out at night, allowing all of us to get a full night’s sleep before the journey began again. The next day, we stopped in Harrisburg, took a break outside of Philly, and then, our greatest mistake, went through NYC at rush hour. Because of this, we stopped not at the Brooklyn Bridge Park as I had aspired, instead, at the New Jersey Turnpike just to get a bit of a break from the aggressive NYC traffic (but ironically, our son won a fox from a claw machine there that is still one of his favorite stuffies-the small things!). We then went under the Bronx via the Hudson Bridge and, sigh of relief, were eventually on the evergreen-lined interstate of Connecticut.
Our stay in New Haven, CT, which was not what we had initially been thinking, was one of the highlights of the trip. We unwound from the car ride and the next day, before getting on the road, spent a few hours playing in the Long Island Sound and admiring the horseshoe crabs. We then, to my husband’s delight, stopped by the Pez Factory located right up the road. Strangely, this was one of the most memorable spots as well, for me because of our pictures of the kids with their faces on top of a Pez dispenser so they looked like one, and for my husband because he bought literal small buckets of Pez. From New Haven we stopped at Providence which was pretty rough, then finished our journey to Osterville. We had arrived!
We stayed for about four days with our friends and enjoyed a kind of backstage edition of a very touristy area. They listened closely to the details of our trip since they themselves would likely be driving back to Indiana to visit family and had kids the same ages as ours. At our destination, we rested, we wore sweatshirts on beaches (new for us who were used to the south Atlantic beaches during the summer!), and we spent some absolute top quality time catching up with our friends. Then, we hit the road again.
On our way home, we took the quicker but unarguably less scenic route, and, since our kids were tired from the beachcombing and Hyannis pirate cruise (highly recommend!), we were able to really push it. (This was the northern route through Massachusetts, New York, Pennsylvania, Ohio, and Indiana.) From when we left Cape Cod, we did not stop until we were in northern New York state where we found a truck stop with a Chik-Fil-A and a play area. Then we stayed the night in Buffalo, once again, just finding a pool, a hot tub, a free breakfast available, and a Hilton room off the app once we got near the city. The next day, since we were so close, we made a pit stop at Niagara Falls, then our next playground was in Cleveland, followed by a long stretch to my parents’ house in northeast Indiana where my kids jumped out of our car and into their pool and my husband and I handed over the parenting responsibilities while we took a much needed break.
This trip was one of my most favorite vacations in my life. By road tripping, my family and I got to spend so much time together, and we were able to be intentional instead of being rushed. Plan a road trip with flexibility in mind. Plan a road trip where the hours on the road are a part of the vacation, not the challenge to get through before the vacation begins. This spring, we are going on a road trip to Duluth, Minnesota, so the kids can see Lake Superior. This trip will only be nine hours, not sixteen, but I know we will have just as many memories as when we went all the way East.
