One of the best things about living in Connecticut was being so close to so many cool places, one of those being Boston. While we didn’t go there nearly as much as we went to New York City (my true love), we went plenty and it’s actually Austin’s favorite spot up there.
We made sure to go whenever my parents visited me up there, too. Since it was only about 1 hour and 50 minutes from Bristol, it was a super easy drive! If you haven’t been, well, you need to. I try to go every time I go back to Connecticut.
It’s a perfect city if you love history, a walkable footprint, the ability to be on the water, and want a city-feel without feeling as crowded or large as Manhattan. Honestly, most people that I’ve met (especially up in CT) prefer Boston to NYC. It’s a slower pace, but still gives you everything I said above.
Don’t forget – Boston is also just about an hour to an hour and a half from Cape Cod (realistically more with traffic…). If you have a decently long trip planned, you must make time to go to the cape. You MUST. 🙂 I’ll do another post on that, but I truly love Cape Cod as well.
Things to do
Boston Common
I may just have too much of a love for parks and walking around in cities, but the Boston Common is one of my favorite things to do in Boston. It’s right in the Back Bay area of town, and such a great place to go and sit with a cup of coffee, walk around, or just hang out.
Boston Harbor
Go check out the harbor area! You can go down to the waterfront and take a boat ride – I highly recommend this – there is so much to learn about Boston! My friends and I went on one that took about 2 hours, and it was so informative, picturesque, and just a great way to see the city from the outside looking in. The one we went on took us out to Georges Island, which I had never heard of until this ride, but the history about it was so interesting!
The North End
This is Boston’s oldest neighborhood, and honestly one of my favorite places to hang out. Just hanging out there, you can feel the history that has taken place there.
-Faneuil Hall: Home of America’s first town meeting – there is SO much history that has taken place in and around this building. You can go inside to get souvenirs, look around, see the rooms, etc. It’s pretty fascinating.
-Old State House: This is the oldest surviving building in Boston (built in 1713) and, to me, the most striking of all the historic buildings.
-There are typically street performers outside of Faneuil Hall…and they are typically great! Every time I’ve been there have been different dance groups that are so impressive that you can’t help but stop and watch.
-Walk across the street from the Boston Public Market to find some of the best Italian food you’ve ever had. Paul Revere’s house is also right over here.
-Walk along the waterfront! Just being on the water is so nice and then you can say you’ve been to the Boston Harbor (and use the accent, of course).
Freedom Trail
This is a trail that is about 2.5 miles long and goes to over 15 historical spots in Boston. I would definitely recommend this if you have any interest in history and seeing some of the oldest spots in Boston (and the country)!
Red Sox game
If you’re there during baseball season, head over to Fenway to take in a Red Sox game! Even if you’re not a Sox fan, it is so fun just to go to the iconic stadium and see the Green Monster in person.
Transportation
Public transportation is big in Boston, and while my favorite mode of transportation is by foot, you can definitely check out the Massachusetts Bay Transportation Authority (MBTA). It offers options like the subway, bus, trolley car, and boat. The “T” which is the subway system there, is probably the most popular and the only one I’ve actually ridden – and it was pretty simple!
Food
I had the best grilled shrimp that I’ve ever had in my life at Legal Seafood (Boston-Long Wharf). It is so delicious and is central to the city.
L.A. Burdick Handmade Chocolates is out of a storybook. You step into the building, and you feel like you’re in a quaint French town. While they have assorted chocolates that are to die for, what I always recommend to people is the hot chocolate. It’s hands down the best I’ve ever had in my life. They have milk, dark, and white, but the white chocolate is by far my favorite. Located in the Back Bay area, it’s also walking distance of the Boston Common.
If you think of an iconic Boston show, I would think and hope that Cheers comes to mind. If you want that Instagram shot or to feel like you’re hanging out with Sam Malone in an underground bar, make sure you add Cheers to your list of places to go! It’s located on Beacon Street just northwest of the Boston Common, directly across the street from where you’ll find Make way for the Ducklings. If you drive here, there is meter parking along the streets just in back.
If you want the whole historical vibe, make sure to check out the Bell in Hand Tavern – America’s Oldest Tavern, which has been around since 1795. The cobblestone streets outside take you back in time, and there are even statues along the street of men in their revolutionary garb. When I walk around this area, I genuinely feel like I’m in a different place and time. It’s so cool.
Faneuil Hall Marketplace has a ton of food options all in a food court style of place. If you want a legit lobster roll or lobster mac and cheese, check out the Boston & Maine Fish Company or Wicked Lobsta. For some good New England clam chowder, try Boston Chowda. If you can’t decide, just stroll up and down the marketplace – you’re bound to find something that you’re in the mood for.
Regina Pizzeria: We would go here before we went to Red Sox games or a few other times we went! The pizza is SO good and authentic! It’s right on Boylston Street.
Hotel
The Boston Park Plaza! It’s centrally located in the city and gives a very historical feel since it was built in 1927. You are in walking distance of the Boston Common and the Back Bay area. (Again, clearly I like the Back Bay area quite a lot).
I truly love the northeast. While Bristol, CT, wasn’t necessarily my favorite place to live, I love that it allowed me the opportunity to go and explore so much of the surrounding area! Everything is so close — the furthest being Washington D.C. which was about a 5 hour drive. Boston and New York City were very frequent trip spots for us, and I just love them so much that I hope to get to go back to the northeast every few years just because I know the great things it has to offer.
Keep in mind, at this time (March 2021) there are still quarantine restrictions in place for visitors coming from high-risk states. If you’re someone from those 45 or 46 states, you must still quarantine for two weeks – so I would put off the trip until you can explore freely!
I hope you’ll head to Boston to see for yourself!
Courtney















