A Weekend in Boston 2020 (with Kids)

If you’re from New York / New Jersey / Connecticut looking for weekend getaway ideas that are kid-friendly, consider taking a trip to Boston. At the moment, you wouldn’t be subject to quarantine either in Boston or back at home, which is obviously important, and many of the tourist attractions and restaurants in Boston are open. Some restaurants are even open for indoor dining, although since the weather is still nice you might as well take advantage of the outdoors. Boston also has a ton of great playgrounds, which is key when traveling with kids. I do have to say the city does feel very empty, probably even emptier than New York, but with the current covid situation, that probably isn’t the worst thing. The following two-day outdoor weekend Boston itinerary focuses on locations close to Downtown, the Seaport District and Harvard Yard in Cambridge.

Day 1 – An afternoon in Downtown Boston

Playtime in Boston Common
Tadpole Playground (Boston Common)

Neighborhood: Downtown
131 Tremont St, Boston, MA 0211

Tadpole Playground, which is located inside of Boston Common, the oldest city park in the U.S., is ideal for those with toddlers. The slides and play structures are manageable for younger kids in that they aren’t too high and have good guardrails in place. There’s also a small but nice fountain area which the kids will love. It’s not the newest or nicest playground–it is in the oldest city park, after all–but it’s centrally located in Boston and it gets the job done.

Dinner at Peach Farm
Peach Farm
Neighborhood: Downtown
4 Tyler St, Boston, MA 02111


If you went to school in Boston, you probably spent a few or many late nights at the Chinese restaurant Peach Farm. But even when you’re sober, the food at Peach Farm is really good. Things to get include the shrimp with mayo, the salt and pepper squid, the Peking style pork and the pea shoots. There is outdoor dining available for parties of up to 6 people.

Day 2 – A day in Seaport / North End / Cambridge

Breakfast pastries at Flour Bakery + Cafe
Flour Bakery + Cafe
Neighborhood: Fort Point
12 Farnsworth St, Boston, MA 02210

Joanne Chang, the pastry chef in charge of Flour Bakery + Cafe, is like the Dominique Ansel of Boston. I’ve been obsessed with her ever since my friend sent me her cookbook a few years ago, and I was so excited to taste her pastries in person. She has several locations in Boston, but I like the scenic walk across the channel to the Fort Point store. Her pastries taste way better than the ones I made in my kitchen (obviously). They’re all amazing, but I would say my favorites are the sticky buns, the brioche donut (only available on the weekends), and the chunky lola cookies.

Playtime at Martin’s Park
Martin’s Park at Smith Family Waterfront
Neighborhood: Fort Point
Wharf on Congress St on the Fort Point Channel

Martin’s Park, a wonderful playground near the Boston’s Children Museum, is just a short walk from Flour Bakery + Cafe’s North Point location. I love the playground at Martin’s Park for several reasons: a) it’s new, b) it’s clean, c) it’s big, and d) it’s fun. There’s a bit of a sad history behind the park, in that it was named in honor of Martin Richard, the youngest victim of the Boston Marathon bombing, but his legacy lives on in a joyful way. The nautical design is a big driver of the fun factor. Kids will gravitate towards the toy ship on the top of the hill and take turns navigating the steering wheel. On the other side of the play area is a huge swing set that is also popular, as well as several slides that let kids go down super fast. Every city should have something like this.

Lunch at Neptune Oyster
Neptune Oyster
Neighborhood: North End
63 Salem St # 1, Boston, MA 02113

Neptune Oyster is a culinary institution in Boston. Pre-covid, people used to line up and wait for hours for the seafood here. Nowadays, you can easily get one of the outdoor tables. The North End neighborhood is a little nuts and is the one section of Boston that still feels touristy, and parking is impossible. But it’s all worth it for the lobster roll and the amazing Johnny cakes, the standout dish at Neptune Oyster. If you’ve ever had a blini, which is essentially a pancake with caviar and smoked fish on top, the Johnny cake is a rich, over-the-top version of that. My son loved this one.

An afternoon of play in Cambridge

Playtime at North Point Playground
North Point Playground
Neighborhood: Cambridge
6 Museum Way, Cambridge, MA 02141

At first, I thought we were driving to an office park, not a playground. We parked and I wasn’t quite sure what we were doing here. But lo and behold, there is a low-key playground that is great for toddlers. The playground is in good condition and the bi-level structures have good guardrails that protect the young and uncoordinated. The fountain area is nice and spacious, and I like how everything is padded down with foam so that the kids won’t get hurt if they fall down. A random location, for sure, but a great playground.

Harvard Square
Neighborhood: Cambridge
Brattle St, Cambridge, MA 02138


Are you one of those people who went to school “in Boston”? Or maybe you push it say you went to school “in Cambridge”? We all know you went to Harvard, you don’t have to be shy about it! Harvard is a big part of Boston’s identity, and no trip is complete without a walk through those ivy doors. Harvard Square was still bustling with activity, and parking was still hard to come by. If you do find a space, stop by JP Licks for some ice cream before heading into one of the gates that take you through the undergrad campus.

Dinner at Myers + Chang
Myers + Chang
Neighborhood: South End
1145 Washington St, Boston, MA 02118

Not only can Joanne Chang bake, she can also cook. Some people have all the luck! You can try out her savory dishes at Myers+Chang, her Asian fusion restaurant in South End. You’ll find familiar Chinese, Taiwanese, Vietnamese and Thai dishes here, but with a twist. I was a big fan of the mussels on toast, a very unique, Asian spin on the French classic. Instead of sopping up the toast with buttery garlic sauce, I was sipping a rich, lemongrass one. The eggplants and dan dan noodles were also good. You can also find some of Flour Bakery + Cafe pastries for desserts on the menu here, which is obviously a great way to end the meal.