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Our 4 Day Road Trip From Connecticut to Boston

Updated: Jun 15, 2021

New England is one of my favorite places in the U.S. Why, you ask? Well, it is incredibly full of history, being the homeplace of the Boston Tea Party and many other historic events. And not only this, but this region is home to some really neat cities, gorgeous foliage and FANTASTIC food! If you're a seafood junkie like I am, get ready for some of the best po boys and lobster rolls you've ever had!

Being someone who prioritizes travel as much as possible while also working a 9 to 5 can be tricky sometimes. Because of this, I tend to be someone who tries to cram as much as possible in a short amount of time. While mapping out my first trip to New England, we knew we wanted to go to at least 4 places: Connecticut, Rhode Island, Cape Cod and Boston.... so we spent one day in each place! I know, I know... this sounds a bit crazy at first and like we are biting off more than we can chew, but it actually ended up working out pretty well! So if you've been itching to head up Northeast and are on a time crunch, you can (hopefully!) find some ideas from our experience for planning your next trip.

--- Day 1: New London, Mystic & Higganum, Connecticut ---

Connecticut was our biggest motivator to go on this trip in the first place. My fiance, Chris, went to college in New London and also has family and friends around the area. So, we hopped on a plane and started our journey from the Hartford airport (We didn't get to see Hartford this time around, but I would love to check it out one day!)

After getting the keys to our rental car early in the morning, we started with an hour drive to Mystic. Everyone back home had told us to have lunch at Mystic Pizza, a restaurant that had it's own entire movie with Julia Roberts! FYI, we never actually saw the movie, but it still felt pretty cool to eat there! Inside they had the movie playing, paraphernalia on the walls, and some pretty good pizza, too!

Mystic was such a pretty place to get to check out, and it truly felt like I was officially in New England. The buildings were colonial-style, the sailboats were out and the ocean was glimmering in the sunlight. Think old-fashioned seaside town and that's Mystic for you! There's also a whole row of small businesses, from boutiques to confectionaries.

New London was next on our list, for a little tour of Mitchell College, Chris's alma mater. It's a small school, but so quaint and adorable! Every time he had something to complain about from his college days, I would always joke with him, 'At least you went to school right by the ocean!' But really though, even if you are just hanging around the area, it is a really pretty campus to check out.

Our last stop in Connecticut would be Higganum, a small, woodsy town where a family friend had invited us into their home to stay for the evening. After hanging out for a bit and taking a break, our next task was to find a spot for dinner. I always like to use my Yelp app to find unique, local spots to check out, and that is how I found out that we were really in a small town! I could count on one hand how many nearby options there were... But, we ended up stumbling upon a really neat restaurant, The Blue Oar. This little place sat right on the Connecticut River, with sand covering the grounds and boats tied to their docks next door. Thanks to here, I was able to try my first 'authentically New England' lobster roll!

--- Day 2: Providence, Rhode Island ---

The next morning, we hopped in the car right after breakfast to hit the road to Providence. The great thing about doing a New England road trip is that the destinations to each place can be so short, with how small the states are. It was an hour and a half trip up, and we stopped at Iggy's Doughboys and Chowder House for lunch in Warwick, RI. Nothing could beat having fish and chips right on the bay!

After checking into our hotel, it was time to hit up downtown Prov. I did some research prior to our trip and was immediately interested in: The Rhode Island School of Design museum. While visiting art museums can be a hit-or-miss for me, this one is pretty unique! Not only are there paintings and sculptures, but also fashion design and other quirky pieces. I feel like it is pretty diverse for just about anyone to enjoy.

A ton of walking around this multi-floor museum had us hungry once again, but this time we were meeting up with family friends who were local to the area. We let them pick out where we would go, and after a failed attempt of trying a burger joint (It was raining so bad that the streets were literally flooding!) We tried a safer option next door, Den Den Korean Fried Chicken. And as awful as it sounds, this was one of the first times I had tried Korean food... and most certainly not the last! I felt like trying the food here was a start of a new era for me!

And lastly in Providence, we were in the mood to nerd out. We're such suckers for barcades, (Bar + Arcade) and ended up finding one that would still be our favorite to this day: Free Play Bar Arcade. The neon lights, retro arcade machines and fruity drinks led for a heck of a good time here.

--- Day 3: Cape Cod, Massachusetts ---

It was time to hit the road again, but this time to Massachusetts. We had originally set aside 2 days for Boston, but thanks to my wild curiosity and spontaneous spirit, we took a detour to use one of those days an hour and a half away in Cape Cod. If you're not familiar with the area, it's an ultra-charming vacation spot that sits on a small Peninsula outside of Boston.

Another thing that we learned quickly was that a single road going up through the town meant god. awful. traffic.... ugh. Nevertheless, we made it out of the traffic and on to our next adventure of the day, which was a lobster roll cruise on the Cape Cod Bay. Let me tell you.... we were SO excited for this! I mean, who wouldn't want to be eating lobster on a big boat out in the ocean of New England? The food was absolutely fantastic... The weather, not so much. It was windy, rainy and made for a very rocky boat ride during our meal. But after returning to cruise near the shore, our experience was much more tolerable!

I think that out of all the places we visited during this trip, Cape Cod was the one I would have put more time aside for. Sure, we had a great time during our one day here, but it's definitely a town that requires more than that to be more satisfied. Before heading on to our next destination, we found a cute little place for seafood, Kream N' Kone. One side would give you a long list of seafood options, while the other was filled with a plethora of different ice cream flavors!

--- Day 4: Boston, Massachusetts ---

Alas, our New England road trip was coming to an end. But before that, we still had one more day to spend in Boston. We met up with one of Chris's friends, a local to Boston, who was a great tour guide for us and showed us all of the best spots of the city.

Boston's a big city, but there was one obvious stop we had to make, and that was at the Quincy Market. Like you would imagine, it's a giant one-stop shop to try all different kinds of foods! We were also pleasantly surprised to see a lot of street performers out front as well, making it even more exciting to visit!

After perusing around the market, we started to walk around and explore more... and this was when we discovered that Boston is a very walkable city! When we needed to head to longer destinations, the train was our best friend. This was actually my first time ever taking a city train in my own country... but it was definitely not as scary as it seemed initially. Heading out of the train station led us to Boston Common, a beautiful park that sits right in the center of downtown. Not far from there, we were highly encouraged to have lunch at Regina Pizzeria. The line outside of the restaurant was insane, but we were assured that it was worth it... and it was! If you want a true, New England pizza experience, this is your place to go.

One last adventure called for an impromptu visit to the New England Aquarium. This one has the coolest interior that I have seen from any other aquarium.... It is essentially one giant spiral with a large tank in the middle, and as you ascend you get to see all kinds of different species!


And so, that was the end of our 4 day adventure, crossing three new states off of our list. It felt like the perfect road trip; short distances yet so many big cities nearby. I was immediately hoping to make another trip up soon to take on the other three New England states: Vermont, New Hampshire and Maine. So, if you've been considering coming up to explore some of these awesome cities yourself, I am highly encouraging you to get out there and check it out for yourself!




Hey there, I'm Shelby! Traveling has been one of my biggest passions in life, and so I'm here to share all of my great finds, tips and advice that I discover along the way. When I'm not on a plane, you can find me in Kentucky with my husband and fur child, Zoe (My adorable kitty!) 

I have always loved to write, and after many attempts at blogging again, I find myself here and inspired to share the world. My husband and I both work a typical 9 to 5, but make it a priority to plan as many trips as possible each year. I want to show others that it is totally possible to live a travel-filled life full time or on the side!

Thank you for stopping by, I hope you enjoy!


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