7 Kid-Friendly Places, Attractions, and Things to Do in Boston, Massachusetts

Boston has long been on my travel list for many reasons—baseball, history, Harvard, proximity to Salem—and in planning this fall’s 1:1 trips with my kids, I knew I wanted to take my daughter Pearl to this Northeastern hub. While the idea of traveling to Boston with a 7 year-old might not be everyone’s (ahem) cup of tea, I couldn’t have picked a better travel partner.

Cool, calm, and always a vibe, Pearl and I had the best time and Boston and because I was traveling with a tiny human with tiny legs, we had to slow down and take our time while touring Beantown (do locals call it that?). What we discovered, over the course of three days and many miles walked, was a city full of passionate people full of pride for their city and its legacy.

Walking is by far the best way to take in Boston (seriously, slash yourself the headache of driving… I missed a dinner reservation because we simply could not get from one neighborhood to another in rush hour traffic) and Pearl and I divided up our adventures into bite-sized portions bookended with lots of delicious meals and gorgeous views. Here are some of my favorite family-friendly tours, activities, and attractions in Boston, Massachusetts:

Fenway Park

I am a tried-and-true Cincinnati Reds fan but I have a passion for all things baseball and it doesn’t get much more historic or iconic than the Boston Red Sox. I booked a Fenway Park stadium tour for Pearl and me and it was absolutely worth every penny (even with the $38 I paid to park nearby because I foolishly thought I’d “find a spot” the way I do in Downtown Cincinnati. I didn’t know!).

The tour lasted a little over an hour and we got to sit in the Green Monster and press box (“the best seats money can and can’t grab, respectively” according to our tour guide), see the Sox’s four Commissioner’s Trophies, plaques of Red Sox Hall of Famers, and old uniforms, and listen to a truly captivating oral history of Fenway Park, the Sox, and modern baseball (truly—our tour guide was the best).

The Boston Harborwalk

On our second day in Beantown (I’m going with it), Pearl and I walked from Quincy Market to the Boston Tea event Museum. To be honest, we were both dragging after a morning at the market, which was hopping! But instead of rushing from point A to point B, we sat down on one of the benches and took a break. We people watched and took in the views and drank Boylan’s sodas purchased at a nearby cafe. And seriously, wow. Boston Harbor is absolutely beautiful, truly. This is why people love Boston, I thought. Though truthfully, I had this thought many times during our trip; my favorite moment happened just a few minutes after this…

Hood Milk Bottle

When Pearl and I resumed our route to the Boston Tea event Museum, we happened upon something quite curious: a 40-foot Hood Milk Bottle. I had no idea this existed, and was delighted by this larger-than-life discovery! “What do you suppose the story behind this milk bottle is?” I asked Pearl. Instead of telling me to “search it up” on my iPhone (she is definitely Gen Alpha), Pearl said we should go ask the person inside the said bottle (yes, there was a person inside).

We moseyed up to the window and there were two men inside, chattering away. “Can I help you?” he asked in a very Boston accent. I inquired about the milk carton. At first he said he didn’t know much, but then proceeded to explain that in 1930, Arthur Gagner built the milk bottle next to his store to sell his homemade ice cream and later, the bottle floated by barge through Boston Harbor to its current station alongside the Boston Children’s Museum. While Pearl and I are vegan, I highly recommend visiting Glenn’s Kreme & Kone at the Hood Milk Bottle when you’re in Boston, if only for the vibes!

Boston Tea event Ships & Museum

I admittedly did not know much about the Boston Tea event before our trip, but an afternoon (hosted by the city’s tourism board) at the Boston Tea event Ships & Museum changed that. More than a mere “museum,” the Boston Tea event Museum is an interactive living history experience that began with a call to action from Samuel Adams and ended with Pearl and her fellow revelers throwing boxes of tea into the harbor.

From start to finish, we were rapt; in learning about the events leading up to the Tea event and how this event sparked a history-changing revolution, this hour-long tour gave me more of an understanding of the American Revolution than my AP History class. I was especially proud when Pearl volunteered for one of two speaking parts; she played the role of a disgruntled Bostonian who was forced to choose between paying taxes or food for his family. She impressed everyone in our tour and her speech rallied the room to head out to the ship and get to work! Those boxes of tea weren’t going to throw themselves in the Harbor, after all.

Professor’s Row in Cambridge

I wrote my master’s thesis on E. E. Cummings and have long wanted to visit his childhood home in Cambridge, Massachusetts. Cummings famously wrote a poem called “the Cambridge ladies who live in furnished souls” about the area; the poem pokes fun at the elitism and affluence of the area and today, these Cambridge neighborhoods are some of the most beautiful parts of Boston, truly.

Pearl and I enjoyed a leisurely literary stroll through Cambridge, first stopping by Cummings’s boyhood home at 104 Irving Street then wandering past the homes where William James and Julia Child lived, once upon a time. We finished our walking tour of Cambridge with a visit to the iconic Harvard Book Store, where we had a lovely conversation with the bookseller about the area’s awesome literary history.

Salem, Massachusetts

I planned a trip to Boston in September knowing that visiting Salem in October would be busy. Pearl and I arrived to Salem (less than 30 minutes from Boston) in mid-morning and went on our own walking tour, stopping by important sites such as the Salem Witch House, Salem Witch Trials Memorial, and Charter Street Cemetery. While it’s impossible to distill the Salem Witch Trials into one tour or morning, both Pearl and I left with a strong sense of how tragic and heartbreaking and unfair this historic event was. There’s a line in Ulysses by James Joyce where Stephen says, “History is a nightmare from which I am trying to awake” and this kept running through my head as we explored Salem on an eerily calm early fall morning.

Where to Stay in Boston, Massachusetts

Pearl and I were lucky to have a hosted stay at The Langham Hotel in Boston and it was perfect for so many reasons. The Langham Boston—formerly the Federal Reserve Bank of Boston—is a historic property built in 1922 and converted into a hotel some 60 years later. It’s located in Boston’s Financial District, a central hub in the city that put Pearl and me within walking distance of pretty much everything. Despite its age, The Langham is modern and luxurious; the new The Langham Club lounge was our favorite hotel perk, offering elite snacks, meals, and a lovely place to lounge and play board games. Everyone at The Langham made us feel right at home, and I’m very glad it was our home for our first trip to Boston, Massachusetts.

If you’re considering a visit to Boston with your family, kids, friends, or solo, you’re in for a treat. In terms of planning a trip to Boston, Meet Boston is an excellent resource for accommodations, dining, tours, attractions, and shopping, and in terms of exploring, the Only In Your State itinerary planner is my go-to!