Our Favorite Street in Boston
Tom and I were in Boston last month and boy, is it our kind of place. Equal parts history and charm with so much to do and we did a lot on our trip. I’ve created a full guide to our trip to Boston that you’ll find at the bottom of this post, but there was one simple, unexpected highlight that I wanted to share with you.
A little background: we stayed in two hotels while we were in Boston. We were there for a convention and Tom’s company put us up in the first hotel. After the convention, we moved to a second hotel, The Liberty, in Beacon Hill.
Beacon Hill, as you probably know, is a charming, historic, mostly residential neighborhood in Boston. And Charles Street, the subject of this post, is a busy street full of restaurants and shops used by locals and tourists alike that runs through Beacon Hill.
Charles Street in Beacon Hill is a destination in and of itself, but since our hotel was at the base of it and so many places in Boston we wanted to visit were at the top, for us it became the most charming route that we walked several times a day.
Charles Street in Beacon Hill
You know by now, that Beacon Hill Books was at the top of my list of places to visit in Boston and it is right in the middle of this stretch of Charles Street. I’ve already shared a lot about this beautiful bookstore, including this post and this Instagram reel, so I guess the only thing left to share is what I bought while I was there. I knew going in that I wanted to get a copy of Make Way for Ducklings for Madeline, and Tom insisted that we also buy her Paige of Beacon Hill, a book about the mascot of Beacon Hill Books, and Paige the stuffed squirrel to go with it. For myself, I picked up a copy of The Library Book, a book I’ve read and loved but didn’t have a copy of on my shelves.
Other places we shopped on Charles Street included gift shops, chocolate shops, stationery stores, and a children’s clothing shop where I bought a ridiculously overpriced outfit for Madeline that I regret not at all.
But our favorite places were the shops, markets, and even the post office (with a window box!) where the locals shopped. There’s something about these tiny, everyday places in the city that we were so taken with. Case in point: we watched a girl walk with her dog into the Charles Street Supply hardware store and pop out a minute later carrying a cooking strainer that she must have needed for dinner or some other task. City life!
As far as eating on Charles Street, our first stop was The Paramount where we arrived starving and sat on the front patio and ate burgers and drank beers and Sangria as we watched people going by. This was also our last stop where we killed time after our delayed flight home. (A true crime detail: we learned that one of the apartments above The Paramount was where the last victim of the Boston Strangler lived and was killed. A less charming detail, but still fascinating.)
Our anniversary fell while during our trip so we made reservations at 75 Chestnut, just a couple of blocks off Charles Street, on Chestnut (obviously). The restaurant was lively and the food was good, but what we especially loved was our window seat looking out onto Chestnut. (FYI, our favorite Boston dining experience in terms of a food + atmosphere + service trifecta was The Florentine Cafe in the North End.)
Back to Charles Street, we got cones from J.P. Licks (twice!) and sat on a bench out front to eat them. And on our last night in Boston, after a nighttime trolley tour and Charles River cruise, we had the Uber drop us at The Upper Crust (their motto: Sort of Famous) where we waited for a pizza and walked with it back to our hotel.
At the top of Charles Street you run into Beacon Street and at this intersection sits the Boston Common on one side of Charles Street and the Boston Public Garden on the other side.
The Boston Public Garden was another highlight of our trip. We stumbled on it (as much as you can stumble on a large city park) on our first evening staying in this part of Boston and it felt like something from a movie. The weather had cooled off and people were walking, jogging, pushing strollers, reading on blankets, and sitting on benches overlooking the pond. We visited the Make Way for Ducklings statue which is just inside the Charles St./Beacon St. entrance to the park and made our way to a bench where we watched people and ducks.
As you can see, Beacon Hill was the most charming home base for us in Boston. Thanks for letting me share it with you.
The Creating This Life Guide to Boston
If you’re planning a trip to Boston, or are just curious about all we did, I created a Boston Guide for Creating This Life subscribers with where we stayed and ate, plus everything we did on this trip. It’s full of links and you can view it, download it, or print it. Enter your email address below and it will be delivered right to your inbox!
Have you been to Boston? What was your favorite part?
I love Boston! Haven’t been there in years though. I loved Back Bay. Best Italian food I’ve ever had in Little Italy. Enjoyed Paul Revere House, Freedom Trail, and really loved everything I saw. We went to Cambridge and walked around Harvard and had pizza and MIT. Watched rowers on the Charles River which seemed like it was right out of a movie. I loved everything about Boston area.
Fern! I loved so many of those same things! Such a great town.