A Northeastern US Road Trip: Part 1
Days 1 & 2
Last summer a friend, my daughter, and I ventured out on a 5 day road trip, leaving from NY. It was quite the experience and I was able to mark off 4 states from my bucket list: New Hampshire, Maine, Rhode Island, and Connecticut as well as revisit two states: Massachusetts and Pennsylvania. We started in New York and headed out…
Warning: This road trip itinerary is far from relaxing, but it was designed specifically for what we wanted: to do and see as much as possible. Many long days with night driving were involved, but it was well worth it in the long run.
Stop 1: Cambridge, Massachusetts (Day 1)
Our first stop was Cambridge, MA, a short 15 minute drive outside of Boston. We set out to see the Harvard University Campus first thing in the morning. We decided on touring the campus on our own in the interest of time, but be aware that there are options for guided tours if you want to take in more of the history of the campus. These tours are timed but free of charge. We spent about two hours walking around the campus admiring the architecture and envisioning what life as a Harvard student must be like before continuing on to our main destination for the day: Boston.
Stop 2: Boston, Massachusetts (Day 2)
We drove the 15 minutes and arrived at our main destination for the day: Boston, MA. We decided on a parking garage located near the USS Constitution instead of attempting to find street parking. Immediately on leaving the garage we were met with downpour, a bit of a disappointment. We spent the first few minutes desperately trying to track down ponchos and were finally successful at one of the museums near the USS Constitution. We spent a quick few minutes touring the USS Constitution before continuing on the Boston Freedom Trail. We made our way to the Bunker Hill Monument (and the rain finally stopped). On our way to Bunker Hill we enjoyed strolling down some beautiful Boston streets.
From Bunker Hill we continued on the Boston Freedom Trail, seeing many historical sites including Copp’s Hill Burying Grounds, Old North Church, the Paul Revere house (stopping for lunch at an Italian restaurant near this location), Faneuil Hall, site of the Boston Massacre, and the Old State House. I won’t get into the details about each of these sites in this post, but each has a significant relevance to American history.
Freedom Trail Sign 
Site of the Boston Massacre 
Freedom Trail Path Marker 
Bunker Hill Monument 
USS Constitution
The Freedom Trail continues for a few stops after the Old State House, but we did not complete it as we had to make it to the Boston Harbor for a whale watching excursion (which would become the highlight of the trip). We made our way down to the harbor and found our way to our dock. We boarded the boat and patiently enjoyed the cruise out to the Stellwagen Bank Marine Sanctuary, anticipating whale and other sea mammal sightings. While ourt on the water we encountered another rain storm, but once again did not let this ruin our experience. We did not spot any dolphins, but we did have three whales hanging out around the boat for about 40 minutes. This cruise was a big hit with my then 2 year old daughter (parents keep this in mind when visiting Boston with toddlers!)
After the whale watching cruise we headed back towards the car, making a stop near Quincy Market. This is a must for any trip to Boston, whether at night when most shops are closed, or during the day for some shopping. We visited at night so we didn’t get the shopping aspect, but we were able to watch many street performers, which was well worth the visit. Such diversity! This concluded the first day of our road trip and we made our way to our hotel for the night.
Stop 3: New Castle, New Hampshire (Day 2)
The next morning we were up and on our way by about 8am. We drove the approx. one and a half hour drive to New Castle, New Hampshire to visit Fort Constitution, an old military fort with the nearby Portsmouth Harbor Lighthouse (our main reason for visiting). We spent about an hour or so exploring the old fort (free of charge). We took in some great views of the harbor and Portsmouth Lighthouse while we waited for the tours of the lighthouse to begin.
When it came our turn to tour the lighthouse we were greatly disappointed. My mini-me did not meet the height requirement to climb the lighthouse. We were therefore turned away, but we did get some good views of the lighthouse. (Parents-keep this in mind if traveling with young children-to this lighthouse or any lighthouse for that matter, make sure you always check the requirements).
After visiting Fort Constitution we continued on to Portsmouth, NH’s Prescott Park where we spent the early afternoon.
Stop 4: Portsmouth, NH Prescott Park (Day 2)
Prescott Park is a water front park in Portsmouth that features gardens, harbor views, and festivals/concerts throughout the summer. We spent some time enjoying the gardens and walking near the water, a nice relaxing break from the busyness of the day before.
After enjoying the gardens we grabbed a bite to eat and headed on to Kittery, Maine.
Step 5: Kittery, Maine (Day 2)
After spending the morning and early afternoon in the sun, we drove the 20 minute drive to Kittery, Maine to spend some time at the beach. We spent the afternoon at Fort Foster, which is home to a beautiful beach and the ruins of an old fort that kids now use for exploration. We spent a couple hours enjoying the cool water and exploring the ruins.
Stop 6: Salem, Massachusetts (Day 2)
We concluded day 2 in Salem, Massachusetts with a Hocus Pocus Walking Tour. Salem is a small, quaint town in Massachusetts that forever has my heart. We spent some time exploring the streets of Salem and grabbing dinner at a local pizzeria before our tour began. We were only in Salem for a short amount of time, but the tour gave us the opportunity to see much of the town. If you are interested in the history of the Salem Witch Trials as well as a big movie fan of Hocus Pocus this tour is the perfect way to explore the town. It took us to many of the filming locations of the movie as well as many historic sites related to the witch trials.
After the tour we headed back to our hotel for the evening, concluding the second day of our road trip. (Stay tuned for Part 2: days 3-5).
Before I go I want to give you a couple of great road tripping tips:
1-Be prepared but spontaneous at the same time! Have a plan for where you want to go, but don’t be afraid to stop and see something that catches your eye! After all, that’s what life is all about!
2-Budget, budget, budget! Make sure that you have budgeted all the essentials before leaving-including gas, accommodations, food, tolls, and activities! You don’t want to run out of money and be stranded. Oh…and a big one if going to any major city…Parking! Prepare for the unexpected!
3-Make sure you have everything you need before you go-check out this road trip packing list!
As always-happy travels!
About Me
I’m Melissa, but you can call me Missy. I continuously crave a new adventure and love sharing those adventures with you! My sidekick is my 5 year old daughter. Together we are conquering the world, one city at a time! Find family travel tips and guides that will help you plan your next adventure!
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Wow, amazing post! The pictures work really well and compliment everything perfectly! Boston harbour is by far our favourite. Thanks for sharing and keep up the great content.
Thank you! I’m glad you enjoyed it! I absolutely love Boston and the harbor was one of the highlights!
Lovely post! and it looks like your toddler really enjoyed it too! I have never made it to the US, so no east or west coast knowledge here, but I will be writing down you itinterary as future inspiration!
Thank you! It was quite the trip, we had many not so great moments, but that made it all the more fun! I would highly recommend a road trip on either the west or east coast if you are able to make it, or even a cross country road trip! That is my next adventure
I love a road trip! And we tend to jam pack our days too! I’d definitely have to do the whale watching tour. That looks like so much fun! We love the northeast part of the USA- what a wonderful trip.
Me too! So much exploring in one trip! The whale watching was probably the highlight of the trip, especially for my then 4 year old! I would definitely recommend it if you have the chance!
Yay, I’m glad you got to do so much in Boston! That’s where I went to school and I really loved it. I can’t believe I never did much day-tripping around the area, like WHY did I not go to Salem, it’s so close and the dark history is right up my alley. Guess I was too busy sTuDyInG or something. Dumb. What’s the best food you had there? Did you get a chance to hit up Little Italy, Newbury Street, or Legal Seafood?
Thanks for the suggestions in Maine, I’ve never been and I’ve been thinking a lot about how I’d love to visit Acadia NP, but I’m not very familiar with the other attractions there. Now I’ve got some ideas!
I love Boston! A big city, but yet it has such a different feel than NYC. I wish I could explore more! I hear you, there’s so much around my hometown that I never visited, I now regret that! I used to be a nerd when it came to school, if only I had focused more energy on traveling! I will honestly say I didn’t get to experience to much of the food, but my favorite was probably a small Italian restaurant near the Paul Revere house. I had some form of garlic and cheese pizza that was delicious, and bruschetta. But nearly every restaurant we passed smelled amazing! When I return I will have to check some more places out. Any recommendations for local places to visit with great food? I did stop in Little Italy briefly, my last visit they had some sort of festival going on. But we did not spend much time there and I haven’t had the chance to visit the other two. More places to add to the list!
You’re welcome! I want to visit Acadia so bad! I would love visiting at the perfect time to view the Northern lights, but I hear that is very, very rare. So many great places to visit!
Yeah, it really feels insular and cozy compared to other big cities. Right?? – I was pretty nerdy too, I had life all wrong lol. That pizza sounds amazing! It’s hard to find bad food in Boston, and some of my favorite places are probably closed now (there used to be this hipster spot across from Newbury Street called The Other Side Cafe I loved that’s not there anymore), but I liked Pavement Coffee, Trident Booksellers Cafe, and Mike’s Pastry!
I had no idea you could see the Northern Lights from Maine! Now I really need to go!
This sounds like such a fun trip. I took my daughter to New York just the two of us and we loved it. It’s so special to make memories together!
It was! We had our ups and downs, but a great experience for both. It is! I love traveling with her and showing her new things! It teachers her so much! I would recommend family travel to anyone!
Such a lovely post! Your little one seems to enjoy the road trip a lot. It is never easy to go for a road trip with toddlers but I think you did a great job 😀
Thank you! I agree, traveling with a toddler is NEVER easy! But it is a great experience for everyone and if you take it at their pace and make sure you are adding in activities they will enjoy it certainly doable!