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Things To See, Eat & Do On A Boston Weekend With Kids

Things To See, Eat & Do On A Boston Weekend With Kids

It’s easy to like Boston, especially with kids along. 

The city’s neighborhoods are compact and easy explore. There are a lot of things to do outside in both summer and winter. It has unique museums for rainy and cold days. And it’s bursting with historic land marks and good food.

Each time we visit Boston for a weekend getaway we have favorite things we revisit. And we always manage to discover new things to do; this is especially true since we began visiting with Tween Traveler. 

We did two weekend getaways to Boston; one in summer and another 6 months later in winter. Here are the four neighborhoods we visited, what we did and ate, what we liked and didn’t. And a few things we reluctantly missed.  

It’s more than a weekend’s worth of things to do. But perhaps you’ll make a few return trips, too, in different seasons.

Cool Things To Do In 4 Boston Neighborhoods With Tweens

History & More Around Boston Common

We spent quite a bit of time around the Boston Common, partly because it seems every walking tour in the city meets there.

A Break In The Common & Public Gardens

The Common is a good place for a sightseeing break or a picnic lunch with younger kids. It has as big fields for running around, an old but serviceable playground and Frog Pond, which children can splash around in when it’s hot. Our Tween liked climbing onto the Frog statues. 

A swan boat glides through boston public gardens full of springtime tree blossoms and greenery.

In summer, the adjacent Boston Public Gardens are a riot color and lush greenery and you can take a swan boat ride on the pond. Walking the winding paths and over the stone footbridge in these Victorian gardens make you feel a bit like you’ve stepped into an impressionist painting. 

Ice skating on frog pond on the boston common with the city in the background

In Winter we brought our ice skates so we could skate on Frog Pond, in the Commons. It was an exccellent ice skating experience.

The rink is huge. It’s in a nice, sunny outdoor setting, and it’s not very expensive. If you like to skate it’s an essential thing to do during a winter weekend visit.  But the rink can be windy; dress your warmest. 

Two Ghost Tours

We did a ghost tour on each of our visits. Both began at the burial ground in one corner of the Common. And each walked a mile-long route that took us past the Granary burial ground and ended near the Parker House Hotel. 

The graveyard at boston common has far more bodies than graves.

We did the Haunted Boston Tour in August, along with a good two dozen other visitors. The guide was an engaging story teller and he made himself heard even with such a large group.

His tales focused on how various poor Boston citizens met unfortunate ends and why they still haunt the burial grounds, the State House and the Boston Athaneum. 

One interesting tidbit: Between the war, epidemics and hangings there are far, far more bodies buried under the Common than there are gravestones in the burial ground, easily a few thousand.

One of the more haunting grave marrkers in the granary burial ground in boston

In February we met up with Boston Ghosts. There was only a handful of us on this tour, largely because the temperature was in the 20s. There was some overlap with the summer tour, but this time our tour guide focused on local ghosts and the people who had notable encounters with them.

Both were very good. Tween Traveler says she like Haunted Boston a bit better but she’d do either again.  

Post-Tour Dessert: Both tours wind up in or near the Parker House hotel, which has had many famous guests. It seems a few guests and at least one former owner never really checked out.

Parker House is the place where Boston cream pie was first served. After both tours we headed to Parkers Bar and ordered it. In the summer we had it with prosecco and in the winter with Irish coffee. Either way this combination of cake, vanilla cream and chocolate is an affordable splurge and an ideal way to cap off a day of sightseeing. 

A Great Freedom Trail Tour With Kids

A costumed interpreter guides visitors along boston's freedom trail

In February we returned to the Commons for a one of the Freedom Trail Foundation’s ghost-free, daytime walking tours. The tours, led by knowledgeable guides in period costumes, are inexpensive and well done.

They don’t walk the entire trail; instead, they wind their way from the Commons to Quincy Market, where the tour ends. 

I’ve walked the Freedom Trail on my own and as an adult it’s certainly doable. But a guided tour is a much better way to do it, especially with kids. The stories and little-known facts bring people to life and add a richer dimension to what would otherwise be pretty old buildings with plaques on the wall. 

We went to the Granary burial ground, a stop on both ghost tours, but it was nice to see it in daylight and to walk around and see the several noteworthy graves.

Tip: The handy thing about FTF’s tours is that once you buy tickets you can show up at any of the several tours they do on most days. At 11:00 on a cold morning our group was still about 20 people. During the summer her I’d choose the first tour of the day or one later in the afternoon to avoid the biggest groups. 

If you’re looking for something more specialized, FTF also offers a tour that focuses African Americans in the Revolution. Another covers the roles of Boston women in the Revolution, abolition, the Civil War and the suffrage movement.

Discover The Boston Public Library

A band that looked like renegade Gryffindor students were playing a set on the plaza outside the Boston Central Library as we walked by. They did us the wonderful favor or drawing our attention to the library building itself, and we went inside to look around.

The marble staircases, murals and grand chandeliers at the boston central library

Good call!  The Renaissance-style building has vaulted ceilings, murals, frescoes, statues and a grassy indoor courtyard. We were all impressed with it. It also has a lovely café that’s a nice spot for morning coffee or an afternoon cup of tea. 

There are free tours of the building daily, but the times vary from 11:00 am to 6:00 pm, so check the website. We would make a point of seeking these out on our next visit to learn more about the building and all its artwork. 

The library is on Copley Square, at the cornes of Boyleston and Dartmouth streets.

Charles Street Restaurants

If you’re near the Boston Common and you get hungry, take a walk up Charles Street, which separates the Common and the Public Gardens. You’ll find take-out and small grocers for picnic fare, cafés, ice cream, and casual and trendy restaurants.

We liked the look of an Italian café and restaurant called Panificio at the far end of Charles Street. It seems to be a café with coffee, Italian pastries and sandwiches during the day and a full menu for dinner. 

They made plain gnocci for tween traveler and charged us half of the price for regular gnocci, making us all happy. Rich had ravioli with a good marinara.

 I had a daily special, which was roasted cod atop of a summery mix of tomato, corn, mango and potatoes.  It was all really good. We would have stayed for dessert but we were saving room for Boston cream pie

Boston doesn’t lack for good Italian restaurants but I’d see this dinner was as good or better than any I’ve had in the North End

Finding The Bar and Restaurant Gems Around Quincy Market

Quincy Market and Faneuil Hall can be fun to walk around if you want to do some light shopping or souvenir hunting. You’ll find plenty of the usual t-shirts and baseball hats.

But we found some unique jewelry at the smaller carts and you can find fun colonial-inspire bags and prints by artisans in a market building in front of the food hall

The colonial facade of quincy market and fanueil hall

But the main reason to go there is that there are a lot of places to eat and drink, both in the market hall and nearby. 

Classic Union Oyster House

Union Oyster House is probably one of the oldest and best known Boston Seasfood restaurants. At first glance it might seem old-school in a stodgy way.  But it’s not at all, and we’ve returned here several times over the years, including on our last visit. 

It’s a busy restaurant with frequent turnover so the seafood is fresh and the service is friendly and not rushed despite the busy dining rooms. I had mussels, perfectly cooked in wine and garlic while Tween Traveler was happy with her kid’s portion of fish and chips.

Rich went with traditional broiled scrod, topped with breadcrumbs and served with bright steamed vegetables.

If you like shellfish, don’t hesitate to order from the raw bar, or pop in at lunch time for a fried clam or fried oyster sandwich.  

A Fresh Take on Sam Adams

We popped into the Samuel Adams Tap Room next to Quincy Market when we had time to kill one afternoon. It’s a nice space; big but not loud.

It also has good pub snacks, like a warm giant pretzel with German mustard. They’re fine with kids in the afternoon and have wide tables that are ideal for settling in with cards or a board game.

A flight of beers at the sam adams taproom

In addition to the original lager and their usual summer and winter beers, they have quite a few beers they only serve at their taprooms. Some seem pretty experimental, like smoked Scotch Ale, spruce lager or piña colada IPA.

We shared a flight so we could try a few and liked most of what we tried, even the more esoteric ones—though I admit we skipped the spruce beer.

We’d go back again because there’s always something new to try and it’s a good place to relax with a card game, drinks and snacks.  

Lunch at Faneuil Marketplace

I have to say up front that I don’t love the food hall at Fanueil Hall because it’s tourist central and always mobbed.  There is a second floor that has more empty tables than you’ll find downstairs. But in the nice weather you can dine al fresco.

The busy two-story food hall at quincy market

But it’s handy with a family because you can agree on a place to meet up and then let everyone go and get their favorite thing. And there are some gems to be found if you pay attention.

We ate lunch here because it was a convenient place to warm up between our Freedom Trail tour and ice skating. Tween Traveler had very good macaroni & cheese from a stand the specializes in it. 

I got a cup of rich, chunky lobster bisque from Legal Seafood, perfect for a frosty day. Apparently, they’ve closed their stall there, which is too bad.

But there are plenty of places at the market to get lobster bisque and New England clam chowder. Prices and no doubt quality vary, so look around. Who knows, maybe Legal Seafood will return when tourism picks up again.

A North End Italian Dinner

On our last evening we made the short walk from Quincy Market to the North End, Boston’s Little Italy neighborhood. It was a cold, rainy night and a homey Italian restaurant was just the thing. 

A street of restaurants and caffes in boston's  italian north end.

We found Antico Forno, known for its brick-oven pizzas and red-sauce pasta and thought it looked kid-friendly. It is, but we had a bit of a mixed experience.  

Tween Traveler was very happy with roast chicken, roast potatoes and green beans.  Her dad’s saltimbocca came with the same roast potatoes and she liked them enough that she ate most of his, too. The saltimbocca itself was on the salty side but his mushroom sauce was good.

I spotted ribbollita on the menu and thought this flavorful bread soup would be ideal for a winter night. It was chock full of beans and vegetables but was soupier and less bready than I’ve had before and not quite what I had in mind. The side of broccoli rabe I had with it was perfectly cooked and garlicky, though.

On balance we’d go back. Next time I’d what everyone else was doing: order pizzas, pastas and salads. And roast potatoes.

Wherever you eat, skip dessert and go find an Italian bakery to indulge in biscotti and espresso, cream-filled lobster tails and cannoli. 

You’ll find plenty of debates about the best North End cannoli but we always just go into the first place we see that doesn’t have a long line (which is anywhere on a rainy night in February). 

This time we happened upon a bakery that doesn’t fill their cannoli shells until you order—the sign of a very good and proper cannoli.

We could build our own pastries with the choice of a chocolate-dipped or plain shell, plain or flavored sweet-ricotta fillings and toppings such as nuts or chocolate chips. (We think it was the legendary Mike’s, but we’re not positive).  

Tween traveled went all out with a chocolate shell, Nutella-flavoted filling and chocolate chips. Here dad went with the classic shell and filling (plain but not boring). I took the middle ground, choosing a chocolate shell and citrus peel in my cannoli cream.

Need More New England Travel Ideas?
An Easy Weekend in Newport With Kids
The Best Things To Eat and Do For Fun on Cape Cod.
A Kid-Friendly Summer Weekend in the Berkshires

Things To Do and Eat Around Fenway 

Even when the Sox are not in season there’s quite a bit bubbling up around Fenway these days and we were glad to check some of it out.

An afternoon at Landmark Park

We walked over to Landmark Park, a relatively new shopping and dining area near Fenway Park, for lunch and more ice skating.

Time Out Boston is an urban food hall that its namesake magazine opened in a converted factory building here. The idea is that they bring noted chefs from across city together so you can sample the best of Boston’s food scene in one place.  

Like Quincy Market, it’s handy with kids because picky eaters can stick to pizza or bagels while you experiment with Armenian kebabs or a gourmet hamburger.

Rich and I shared clam chowder and a Cuban sandwich while Tween Traveler tucked in to Greek chicken wings.

For dessert it was tough to choose between the creative fillings and frosting at Union Square Donuts (Vietnamese coffee, anyone?) or the creamy goodness at Gelato & Chill.  In the end, chocolate gelato won the day and I can’t say it was a bad choice.  

On your way out, stop by the camera that projects onto the way a pixelated image of you that tracks your movement (top).

A seasonal ice rink in landrmark park near fenway park.

In 2020 they set up a very small temporary ice rink on the green outside the food hall. On the day we were there, temperatures had popped up into the 40s and they ice was a little slushy, to be honest. 

I noticed they didn’t reopen it this year, mostly likely because of Covid. I hope they bring it back again, maybe with a stronger icing machine. It was a nice addition to the area. 

During the summer the ice-skating area is a sizeable green space. Trillium Brewing Company has a taproom to one side with a big glass window and outside patio. It seemed to me like a good spot to settle in for a good pint and fun people watching at any time of the year.

Cambridge With Kids: Bookstores, Museums & Restaurants

We had planned to take the T to Harvard Square and spend a good part of a morning perusing the area’s many bookstores. But we emerged from the train station into a downpour that continued to a greater or less extent all day.  

No matter; we still found interesting things to do.

Books and Comic Books

The facade of harvard book store in cambridge, ma.

We did manage to visit Harvard Book Store, which has a well-curated children’s section and plenty more besides. Tween Traveler picked up a book about coding on Scratch.

We also popped in to Newbury Comics, which is hidden on the second floor of a quirky mini-mall. 

Newbury is a fun store that sells weird stuffed animals, slightly subversive card games, many-sided dice and figurines for roll-playing-games, vinyl records, silly t-shirts and more. Somewhere in the store I think they also have comics. 

Comic book fans should also seek out New England Comics and Million Year Picnic. All three stores are within a block of one another.

Raven Used Books and Grolier Poetry Book Store are on opposite sides of Harvard Square (Raven is closer to the T), but we didn’t get to those. Maybe next time.

Head down Massachusetts Avenue just as we did and halfway to MIT you’ll come across Pandemonium Books, which has the most boring, non-descript façade a bookstore can have. Go in anyway.

Pandemonium specializes in science fiction, horror & fantasy books. If you bypassed Newbury Comics it’s also another place to stock up on dice, Magic: The Gathering cards, roll-playing-game manuals and boardgames. 

I think I’m lucky that we couldn’t tell from the outside what the store was about; if we had stopped in Rich and Tween Traveler would have stayed all day.  Next time, for sure.

Check Out The MIT Museum

Our destination at the other end of Massachusetts Avenue was the MIT Museum, which features some of the innovation coming out of the university. 

Tween Traveler, who brings a Fuji Instax everywhere she goes, liked an exhibit the showed how instant cameras have evolved from the 1950s until now. She even got to hold a couple of (huge and heavy!) antique models that they had out for visitors.

A motion machine is moveable art a the mit museum in cambridge, ma

We all also liked a room full of motion machines, essentially moving sculptures that merged art and physics. Some were fun; some were odd. They were all interesting.

A room with robotic body parts was less hands-on than Tween Traveler would have liked. There was a classroom for kids, but the day’s hands-on activities were too young for our tween. 

Tip: The kids’ actities aside, I think this is a science museum better suited to tweens and teens who are outgrowing the typical kid-centered science museums.

It wasn’t the overwhelming success I hoped it would be with my STEM-loving kid. But it’s one of those museums that’s always worth stopping by. It’s small enough that you can see everything in an hour or two, and the handful of exhibits change constantly.

Tip:  From September to June admission is free on the last Sunday of every month.

Sample Harvard’s Many Museums

Harvard has a half dozen museums on campus and you could make a day of exploring all of them.

The one we missed and want to go back for is the Collection Of Historical Scientific Instruments At The Putnam Gallery. It include mathematical, medical, astronomical, navigational and time-keeping devices dating from the late 1600s to early computers and radios. 

We did go to the Museum of Natural History, which connects to the Peabody Museum of Archeology and ethnology and the Museum of Comparative Zoology. 

Despite encompassing three museums it felt small.  If you’ve been to the Natural History museums Chicago, Washington, DC and New York it will seem underwhelming. But its size makes it’s manageable with smaller kids.

Realistic and scientifically accurate glass flowers at harvard's natural hstory museum.

The unique, can’t-miss thing to see is the gallery of glass flowers. Made by Czech artisans in the late 19th and early 20th centuries, the flowers are meant to be scientifically accurate renderings of nearly 800 kinds of plants. Some even show depict how fruit decays. 

It really is cool. It’s also the kind of thing I could spend a half hour perusing while my kid is ready to move after a few minutes. Luckily, I could send her ahead to the planetary sciences gallery while I lingered.

The university also has several small art museums focusing on Asian, European, American and German art, respectively, and the Museum of the Near East, which delves into the history, culture and languages of countries along the Eastern Mediterranean and north Africa into Iraq.

Kid-Friendly Restaurants in Cambridge, MA

Massachusetts Avenue has the full variety of ethnic and vegetarian restaurants you expect to find around college campuses. They’re casual and definitely kid-friendly.

The rain and cold make us crave something heartier than Thai or India and we found what we wanted at the Asgard, an Irish Pub closer to MIT.

Tween Traveler went directly for spiral pasta in an oozy cheese sauce; she says it’s some of the best mac & cheese she’s tried. I had tomato soup and grilled cheese on sourdough, the classic rainy day combo. Rich went traditional with a shepherd’s pie.

A few blocks back toward Harvard is New City MicroCreamery, your spot for small-batch locavore ice cream. In addition to the usual flavors try seasonal specials like cran-cherry or pecan-pie, made with molasses.

If you need a pick-me-up after all those Harvard museums, head to Zinnekin’s Belgian Waffles for coffee and waffles topped with bananas, berries, chocolate, Nutella and whipped cream, among other things. They’re impressive and shareable. It’s a few blocks from campus at the top of Massachusetts Avenue.

Discovering Fort Point & The Seaport

Each time we return to Boston we visit Fort Point and the Seaport District, across the channel from Downtown. Each time there seems to be more restaurants and things to do, especially with kids.

Kid Fun On the Waterfront

When we were visiting the city with a Tiny Traveler, The Childrens’ Museum was the thing we had to do. It’s one of the best Children’s Museums in the country.

The giant factory space that is now the boston children's museum.

The fun offered across its three floor includes a giant climbing structure, an authentic merchant’s house from Kyoto, a hands-on STEAM lab and a room full of Keva planks for building.

Read More: The 10 Best Children’s Museums in the U.S.

Next Door to the museum is the Children’s Wharf Playground, which is an awesome playground. Long metal slides, a large atom-like climbing structure, rocks, steps and a wooden ship will keep kids up to ages 10 or 12 occupied while you enjoy the harbor views.

Winter Activities at Snowport

Part of Boston’s Seaport district turns into Snowport during the winter with curling, outdoor art and light displays, igloos and a wandering Yeti.  Be sure to wander down the side streets to find coffee, snacks, lunch if you need to warm up after some outdoor winter fun.

In some years there’s ice skating. It seems to be suspended for this year in favor of a more low-key experience. 

The Boston Tea Party Experience

Over the summer we booked tickets for the Boston Tea Party Experience, which takes place on a period ship in the middle of the Fort Point Channel.

The Tea Party fun starts with a town meeting about the tea tax issue in a colonial meeting hall. We were all given identities of people who were known to participate in the tea party and we had the opportunity to speak up in character if we wanted to.

Known personalities of the day, like Samuel Adams, got the group riled up and indignant about unfair taxation from England. Huzzah! Then we headed out to the ship. The captain assured us we’d get no trouble from him. Huzzah! Then we got to throw bundles of tea (attached to ropes) overboard. Huzzah! 

It was a fun way to experience a moment in history we’ve all heard about, and it clears up some of the apocrypha around this event. I’d been wanting to do this for a while because it’s a great way to learn more about the Boston Tea Party with kids.

But I do wish we’d gotten to it sooner.Third through sixth grade is the sweet spot for the historic reenactment. My rising seventh grader was too cool to “Huzzah” with much enthusiasm And there was a bit of eye-rolling when I got too carried away.

We liked the (inevitable) gift shop. I even bought some nice tea that was thought to be a typical colonial blend.

Lunch at the Barking Crab

If it’s a nice day, lunch at the Barking Crab is the perfect way to follow a morning playing at the Children’s Museum or protesting the tea tax.  And we’ve done it after both.

This popular seafood restaurant has a huge tented outdoor space right on the water. On a warm day it’s hopping. When we visited over spring break a few years ago we managed (just barely) to get an outdoor table (below).

A lucky dad and daughter at an outside table at the barking crab in boston.

In summer, even on a weekday it wasn’t happening without a wait. We did get a table inside pretty quicklu. It was suitably nautical, we had a nice water view and truth be told it was a bit quieter than outside.

On our first visit Tiny Traveler asked for mac & cheese off the kids’ menu.  This time around she eagerly tucked into fried calamari.

Rich and I just indulge in New England shellfish when we come her and share some combination or raw or grilled clams, steamers, seafood chowder and crunchy crab-filledcrab cakes.  And of course, we drink pints of Harpoon because, what else would you drink eating clams on the waterfront in Boston?

More Things To Do!
Book a historic Beacon Hill home or cool Cambridge flat for your family
Save on admisson to the Boston Zoo, Aquarium & Science Museum with CityPass.
• Or save time with skip-the-line tickets for the Aquarium

Boston Hotels

On both of our visits we stayed at the Back Bay Hilton. We had free-room points with Hilton and this was the only Hilton hotel downtown with a pool. 

But we often stay in the Back Bay area anyway because it’s easy to get anywhere in the city from there by foot or by T. It stretches into a more residential area, too, so there are plenty of restaurants and shops around.  

On the first visit we had corner room, which provided extra room for us to spread out our luggage. The second time around the room was more standard; comfortable but not quite as roomy.

The pool is on the small side but deep enough for adults. The water was pretty chilly on both visits and, especially in the winter, we really wished they had a hot tub alongside it.  But any pool is a good pool as far as Tween Traveler is concerned so we were happy with the choice.

We didn’t bother shelling out for hotel breakfast because local coffee chain Flour Bakery & Café had a store right across the hotel. We were very happy with its croissants, chocolate brioche and scones. They have egg sandwiches and avocado toast if you want something more.

On a previous visit when our main purpose was to visit the Childrens’ Museum, we stayed at the Westin Boston Waterfront, on the Fort Point side. It has a good size pool with a comfortable deck. Our room has space to walk around even after they added a roll-away bed. 

It has a Starbucks in the lobby and all of Fort Point’s restaurants and coffee bars right nearby as well as its parks and attractions. The hotel had a shuttle service to Quincy Market which made is eay for us to explore downtown.

The Westin connects to the convention center. When there isn’t a big event going on you can find good rates there and at other nearby hotels.

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Photos by FamiliesGo!© except Public Gardens, Common Burial Ground (Visit Boston), Public Library (BPL), Boston Childrens Museum (BCM), Harvard Book Store (Adam Fagen/Flickr) and North End (Wikipedia).