In 2020, I told my husband I wanted to do a big road trip in the summer of 2024. My husband, even knowing me and how far I plan into the future, was surprised I was planning so far ahead. But at the time I was on a long-term project and I suspected that it would end around that time (news flash, I was right). I also knew that it was at a time right before summer jobs and experiences would start to be important for my oldest’s resume. I thought it might be my last chance to have a full summer of travel with my kids. While I did have the summer, due to some circumstances (I did not know Taylor Swift would have an epic European Tour that summer) we did not have the whole summer to do a road trip. But I still wanted to get some of that experience in. Check out how I road-tripped the East Coast with my two teens and what we learned from the experience.
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Why We Did It
I have always wanted to do a long road trip with my growing kids. When they were younger, road trips were scary. They did not like to be in the car for more than 2 hours. I had to find ways to entertain them. They had more needs. And they could not help. But now they were 14 and 12. They could carry luggage. They could help with the plan. And they could be more involved in the process.
I promised myself I would do a road trip in the summer of 2024. I said that if my grandmother was still alive in the summer (she had been put on hospice care the fall before) I would take the kids to the east coast for a few weeks, and we would do a shorter road trip on the east coast as opposed to a longer one on the west coast. As my grandmother is still alive, we chose to go that route. The kids wanted to make sure to have plenty of cousin time as well, so we negotiated a route that took them to new places and prioritized plenty of cousin time.
Itinerary
- Day 1 – Drive to Small Town Connecticut in the evening.
- Days 2 & 3 –Small Town Connecticut
- Day 4 –Hartford / Drive to Boston
- Day 5 –Boston
- Day 6 –Boston / Drive to New Hampshire
- Day 7 –Hanover, New Hampshire
- Day 8 –Drive to New Hyde Park, NY
- Day 9 –New Hype Park NY / Drive back to New Jersey
Small Town Connecticut
We went to Small Town Connecticut with my sister and her kids to visit my godparents who were so excited (if not overwhelmed) by having us all come to visit. But I was excited to show the kids how cute Connecticut can be. We went to the local beach with a splash park. It was a quiet inlet where the kids could go out deep without worry. There were horseshoe crabs and hermit crabs they could see for themselves which they loved.
We also checked out the local art festival and library. The library had a fantastic children’s room with arts and crafts, a train table, and more. My niece and nephew enjoyed doing crafts and playing in the room. My oldest found the teen room and was trying to convince my godfather to check out a book for them and they “promised” they would finish reading it before we left. My daughter found the used book sale and perused the CDs and books to purchase.
Plus, we just had a backyard barbeque and enjoyed being together as a family. That is one of the things that is so important for me. Making sure my kids stay connected to their family and roots. My daughter and Cool Cousin A (my godparent’s daughter) ganged up on A’s girlfriend and my Oldest in a game of Blongo. We ate hot dogs and hamburgers and laughed until the sun went down. It was a beautiful way to spend time together.
The last morning, my sister packed up her kids and went back to New Jersey as they still had a few days left of school. Me and my kids headed out to Hartford, Connecticut.
Hartford, Connecticut
Sea Tea Improv Studios is an organization Cool Cousin A is involved with in Hartford. She informed us that every Sunday they had a family friendly improv show. My kids unanimously decided we had to prioritize going. We drove to Harford where Cool Cousin A walked us around the cutest street in the city. We were there during pride and were excited to see all the support for the community in the city. We ate at a local pub, checked out little boutique shops, and even enjoyed a float at an honest to goodness Soda Shop. Then it was time to see the show.
If you have never gone to an improv show, make it a priority. No two are the same. The show is driven by input from the audience and you end up with some hilarious skits and situations. You can also see how talented these comedians are as they have to come up with how to handle the suggestions given on the spot. Adult shows can get raunchy (as you can imagine) so it was nice that they cut out shows specifically for families. They even take volunteers from the audience. Of course, my daughter wanted to be in, but having Cool Cousin A on the stage pull her on was helpful.
After the show we hugged my cousin goodbye and headed to Boston to stay with her brother and his husband.
Boston
My cousin K and his husband J have a lovely home in East Boston and offered to host us during our stay. We were in Boston to see the sites, but it was also nice to have a place to stay and spend evenings with them.
We were in Boston for the Freedom Trail. Both kids had studied the revolutionary war, but, living on the West Coast, never got to really see any of it outside of books. Meanwhile, I grew up on the East Coast, so I had learned by visiting sites.
The Freedom trail is 2.5-mile trail of sites all throughout Boston. It starts at the Boston Commons and goes throughout downtown Boston, across the Charles River, and ends at the Bunker Hill Monument. We stopped at the visitors center in Faneuil Hall and got maps and downloaded the app. Walking the trail and most of the sites are free, but there are a few that require a purchased ticket to enter. Then we walked to Boston Commons and followed the path and visited the sites. Some of our favorites included…
- Granary Burying Ground – Here we saw the grave of Samuel Adams, the grave for the parents of Benjamin Franklin, and the grave marker for the victims of the Boston Massacre.
- Old South Meeting House – Here we paid to enter, and got to listen to stories of different meetings that took place here, from the first meetings for the Boston Tea Party, to abolitionist groups during the Civil war.
- Old State House – Another paid museum, you get to see the King’s Council Chamber where the most powerful men in the colonial government met. We also got to see a temporary exhibit. At the time we went, it was an interesting take on the Boston Tea Party and other protests, it had you thinking about if property destruction helps or hurts the cause and re-thinking the story we were told about that event.
- Paul Revere’s House – Our final paid entrance, you can see the house where Paul Revere and his wife raised their 16 (yes, 16) children. There is also an exhibit at the silver shop and his Famous Ride.
We ended up stopping at the Old North Church because of how hot it was that day and we were done walking. But, I have been to the other Bunker Hill Monument in the past and it is worth the visit.
We also decided that we needed to do the famous Mike’s vs Modern’s Challenge. North Side of Boston is a famous Italian district and known for two famous Cannoli shops, Mike’s and Modern’s. In Boston, you have a clear favorite, it is a must. We decided to get Cannoli from each and figure out what we liked best. It was split. I liked Mike’s but my daughter liked Modern’s. My oldest, ever the diplomat, liked the vanilla from Mike’s and the chocolate from Modern’s.
On our second day, the kids wanted to visit the Museum of Science. We spent the morning exploring the different dinosaur, engineering, and robot dog exhibits in the museum. It is a fun museum and if you have science fans, it’s worth a visit.
After lunch, we headed to walk around MIT. My daughter has had her eye on that school for a while now, so we decided to check out the campus. We mostly spent the time walking the Infinite Corridor. This is a famous long hallway that connects multiple buildings on campus. We got to see the Memorial Lobby, the Laboratory for Advanced Materials (LAM) and colorful murals. I enjoyed walking past the posters for groups on campus. My daughter, the creative, was happy to see that a “science” school still had fun things like a South Asian Acapella group. My oldest quickly found the post for the Dungeons and Dragons group.
Afterward, it was time to head back to East Boston and collect our car and pack our bags. We had a short two hour drive up to New Hampshire.
New Hampshire
We went to New Hampshire to visit one specific place – I wanted to show the kids where I “grew up” – Dartmouth. I was lucky enough to attend this esteemed institution, and it shaped who I am as a person today. I still say that attending Dartmouth was one of the best decisions I made in my life. It was that pivot point that opened my eyes and led me down the path I am on today.
I had signed my oldest up for an official tour of the school, but that was in the afternoon. In the morning, we walked through campus as I pointed out where I had lived and ate on campus. We walked into town and I talked about the shops we used to visit. We ate breakfast at Lou’s, one of my favorite spots as a kid. We had hot chocolate at Dirt Cowboy, my favorite coffee spot. And we walked on The Green, where I spent countless hours studying and hanging out with my friends on a gorgeous day.
We went into the library, and a librarian was able to help me find my math thesis on the shelves, and I saw it was even checked out a few times in the last twenty years. My kids were so excited to see my “published” work on shelves, and to be honest, it made me proud to. My legacy was still there. We also walked through my favorite study room in Sanborn library, and the murals in the Orozco Room. Then we went over to the Math building, where I found a admin who had been around since I studied there. She caught me up on all my favorite professors and gave us some free Dart-Math merch
During the official tour, I got to learn a lot about how the institution has changed over the years. New buildings were there, new courses of study were available, and there was a significant effort I could see to provide alternatives to Greek life, something that was not as successful when I attended in the late 90s. I loved seeing the changes and the institution I love grow and change with the times. I also enjoyed talking with the student and seeing how much she loved being here. A few parents talked to me afterwards and I reiterated how much I feel like the experience affected my life. I hope that a few of those kids get in and choose to attend.
My kids let me know that they did not really see themselves at Dartmouth and believe it or not, I understand. I grew up in a small town without much world experience. I needed a small place with like-minded people to open myself up in a safe way. My Californian kids grew up with educated parents, diversity at every corner, and with access to a city and its services. They do not want or need a small school in New Hampshire. I however, have faith that they will be able to have an amazing experience wherever they choose to go.
New York
Driving down to New Hyde Park, we decided to make a stop in Rhinebeck. This cute town in upstate New York is known for having excellent food options, cute shops, and a sweets shop owned by Paul Rudd. We did not know that when we entered, but I can tell you we all LOVED the treats we got from the shop.
Afterwards, we went to Poughkeepsie where we checked out the Mid-Hudson bridge. We ended up not being able to walk on it because we went to the wrong spot and the path that led to it ended up being blocked. But I have walked it before and it gives a stunning view of the Hudson River.
We instead went to Shadows on the Hudson where we had a fantastic meal made by a Culinary Institute of America Chef, and got seats on the balcony, overlooking the Hudson. This was the fanciest meal we had on the trip, but since we knew we were in a foodie town we had to make the splurge.
The next day we headed to Val Kill. The Franklin Delano Roosevelt National Park Complex actually consists of three homes, FDRs home, a Vanderbilt summer mansion, and Val Kill, Eleanor Roosevelt’s “cottage”. This was the home that FDR bought for her and where she spent most of her time and lived after FDR’s death. My sister worked for the estate and this was my favorite place out of the three. We were able to make it in time for the 11 AM tour. Here the guide walked us through the home, where we learned about its history as a woodworking shop, and saw some of the furniture in the home. But this home looks lived in. You could see the mismatching chairs and China in the dining room. You see how crowed it is and know what it must have been like to have a meal with this woman. You can see the cozy reading corner where she and John F Kennedy met and first talked about the Civil Rights Act. You can see the mixture of pictures on the wall of places she had been mixed in with pictures of family and friends. The kids loved the stories of parties at the pool and Eleanor holding all in her presence to the same high standard, whether it was her own family or the children of the “help”.
After the tour and walking around the grounds, we headed to the Culinary Institute of America. There we ate at the Apple Pie Bakery Café, which is the casual café that does not require reservations. We had some fantastic focaccia, and desserts that were to die for. We also got to talk to a student/server who told us about the different courses and training they give at the institute. We chose to not take a tour, but we did find the hallway dedicated to my travel hero, Anthony Bourdain.
Tips
- Let the Kids Plan – We sat down and talked about what direction to go, what cities to visit, what to see in each place. We spent so long in Connecticut because the kids wanted time with family and cousins. We went to the Museum of Science in Boston because they cannot pass up a science museum. Instead of exploring more of small-town New Hampshire we choose to spend the afternoon in the pool and have fun. Sure, I had a lot of suggestions and provided guidance but having them in the process made them want to engage.
- Assign Roles –They could not drive but they could help. My oldest was the navigator and in charge of the radio and entertainment. My daughter was on snack duty, required to give out snacks and drinks when needed. It was all discussed beforehand and they got to choose their roles.
- Audio Books for the Win – This is one we have been doing for years but is still a winner. For this trip, since we were preparing for our Poland trip, we listened to “We Were the Lucky Ones”, an epic novel about a family of Jews in Poland who were all separated over the course of WWII but somehow all survived. It is now a mini-series on Hulu that is highly faithful to the book. This book, however, can have some difficult scenes so I do not recommend it for families with younger kids. The advantage of having teens however, is that you can listen to some more mature, interesting stuff.
- Pace the Driving – Since I was the only driver, I decided that there would be no more than four hours of driving in a day. We considered going all the way to Niagara Falls, but to fit it into our time limitations, it would have required me to drive longer than I was comfortable. Understand what your limitations are and how many drivers you have when planning a route.
- Use Family and Friends Where You Can – Boston is expensive! I’m so thankful my cousin offered to host us. We were there at mid-week so we made sure to get out in the mornings so they could work in peace. But we got to have dinner every night with them and still get some quality time together while exploring a new place!
- One big suitcase is better for packing – I am normally a carry-on only girlie and encourage the same. But it is different when it is a road trip. You have more room. We decided to put all our clothing and stuff in one giant suitcase, and each have a small backpack or day bag. This way, there was less stuff that needed to be taken out and packed back in the car every time we changed locations.
What to Bring/Wear
- Small Cooler and Snacks – What is a road trip without snacks? We used a small cooler to hold a few drinks and some fruit while driving. We had another bag that held road trip snacks. We would often just stop at a convenience store to stock up so we did not have too much at once.
- Proper Footwear – We did a lot of walking everywhere we went, so for us, comfortable walking shoes were necessary. I did the whole trip in my Bob’s Slip in Sketchers with memory foam. The kids love their Sketchers Go Walk Sneakers. If you are including some hard-core hiking, make sure to bring comfortable hiking boots.
- Selfie Stick/Tripod – I am always nervous about giving my phone to a stranger to take a family picture. I have found that the selfie stick, while annoying, can get in the whole family with a nice background in the distance. But I really like this Self-Stick/Tripod, that allows you to set up your phone with a tripod so you can take pictures from a distance with a Bluetooth remote, and it does not feel as intrusive as a selfie stick.
- A Good Day Bag – You need a bag that will carry all the essentials for the day (hand sanitizer, your phone and wallet, snacks, etc.) I used the Pincnel backpack which held snacks, a battery backup, and any other essentials we needed for the day.
- Handheld Fan – The East Coast is hot in the summer. I saw many with these portable neck fans and I wished I had one. If you can find one, and are going anywhere in warm, bring it.
- Duffle Luggage – I ended up getting is Delsey Duffle Suitcase at Costco and loved it for this trip! It was big enough to hold all our clothing for a week, but the handle on the side made it easy for lugging in and out of the car everyplace we went. It is my new favorite road trip bag.
A road trip with teens is a totally different experience than a road trip with little ones. We got to listen to a mature book and have meaningful conversation about it. We got to explore places on the fly that they found interesting. We checked out food that we might never have done when they were little. And we also sometimes caved to our desire for a fast-food quick hit. We listened to tunes, and the kids learned how to use Google maps to find restaurants, stores, and other things near where we planned our next stop. We laughed at jokes and made memories together. As my kids grow, I understand that my time with them is shortening and I want to make these memories while I still can. Pull out Google Maps, sit down with your teens and plan that road trip. It is fun and an experience you will not regret.
Edited by: SKS