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  • Writer's pictureDr. Jessica Dello Russo, Ph.D

Vacation Liberation: The Kid-Friendliest Boston Tour

I spent my early childhood in close contact with monuments of Boston’s past. My home was a block from that of Paul Revere. My preschool had a large statue of colonial governor John Winthrop by its front door. The parish church I attended was located in North Square, one of the oldest designated public spaces in America. Traveling daily between home and school, I crossed Dock Square with a statue of Samual Adams at its center. I knew these men by name. 


Aside from putting names to faces, my preschool self could have told you that these peculiar-looking people and buildings were old. With some prodding, maybe that colonial homes had farm animals and weapons and big fireplaces and homemade butter (there’s always that first trip to Plymouth Plantation). 


In the end, though, what stands out in my earliest memories of Boston’s historic neighborhoods is childhood itself. Chasing squirrels. Drinking lemonade. Trying to climb up a lamp post (or one of the statues). The grand prize of somehow getting myself soaked (in a puddle, a spray pool, or even the Charles River). Yes, I was that kid who got into everything. But don’t tell me you were very different! Hands-on encounters with the rough and tumble fabric of a major city is absolutely a valid and lasting learning approach. Young children by and large are curious, adventurous, and open minded. They can rapidly absorb their environment and develop a strong sense of belonging to it - you would think that they owned the place! They are explorers who need to figure things out. As they make demands on your time and patience, they are testing their own ways to adapt and still be their curious, receptive selves.

You’ll see this playing out in high gear during the family vacation in a new, unfamiliar setting. There you are: parent, planner, and guide to the next snack bar, rest room, pharmacy, souvenir stand, any place in the shade!

There is your kidlet, possibly tired, hungry, bored, or otherwise distracted until they spot the way out. I’m assuming you have opted to go device-free. With qualified exceptions, hang in there! Pack a pair of binoculars instead, or invest in some type of malleable souvenir. If your smartphone is a last resort, try loading a GPS app or digital guide to your itinerary. Incidentally, hiring a living, local guide is a huge help in keeping everybody - yourself included - device free.


So why make all this effort to travel? I’m making it sound just like home! Exactly! Your kids in their hyper-distractibility are finding ways to belong. They won't catch on then, but their responsive, even fearless engagement with new surroundings won’t be just a memory. First impressions really are lasting.


As to where you are headed, here’s my advice. Instead of focusing all of your energies on the 2.5-mile long Freedom Trail, Boston’s best-known historical itinerary, I recommend (weather permitting) the Boston Harborwalk as the main route through different neighborhoods of the city. Very often the two routes are within a few blocks of one another and are one and the same between the North End and Charlestown. Boston’s earliest settlement in 1630 was on the harbor (although the shoreline today is largely made land). With Boston Harbor on one side of you, there are fewer streets to cross, more open spaces, and mostly level, pedestrian-friendly sidewalks. Because so much of the Boston Waterfront has been recently developed or repurposed, you are able to access all of its Chapter 91 (Massachusetts Public Waterfront Act) public amenities, including bathrooms, observation decks, snack bars, drinking fountains, visitor kiosks, and historical place markers. Best of all, if you need/want to use public transportation, it can be in a boat! 

The starting point for touring Boston with younger children really depends on the timing and weather during your trip.

One place to begin would be the pedestrian-friendly Charlestown Navy Yard. In addition to multiple vehicle drop off points around the perimeter, there is a year-round, public transit ferry from Long Wharf that brings you right to the nearest public dock.


The star attraction, of course, is the USS Constitution, “Old Ironsides,” the oldest commissioned warship in the entire world still afloat. The vessel, first built in 1797 and still today operated by the US Navy, is regularly open for free public visits (government-issued ID required of adults). Once aboard, you are on your own to climb up and down the narrow stairs and walk across the decks (not all levels are ADA accessible). The sailors on duty are extremely knowledgeable and welcome questions. At a neighboring dock is another historic vessel open to tour: the World War II-era Fletcher-class destroyer, USS Cassian Young. It offers a maze of corridors and an intimate look at the 20th-century naval experience. I have witnessed time and time again that boarding and exploring these ships is something that kids really enjoy. 


The visit to Old Ironsides also includes an indoor exhibit on US Navy operations in the Charlestown Navy Yard Visitor Center, but for a fully interactive historical immersion head next to the USS Constitution Museum. The younger set will really - and literally - get into the “Sailor’s Life” experience and “Lego Brickyard”: the museum also provides special opportunities like “Sensory-Friendly Sunday” for those who might need a quieter environment in which to experience the museum.


The Charlestown Navy Yard is one of the terminal points of Boston’s Freedom Trail, a self-guided itinerary marked by a continuous red line. It brings you to many - by no means all - of the city’s Colonial-era buildings and memorials of the American Revolution. While you’re still in Charlestown, you might opt to follow the Freedom Trail around the Bunker Hill Monument and adjacent Bunker Hill Museum, both free to enter. As you might expect, it’s a bit of a hike to get there, and very much so if you elect to climb the monument’s two hundred and ninety four stairs to the top! That part is up to you, but be sure to see the monuments to Revolutionary War heroes General Joseph Warren and Colonel William Prescott and recognize their bravery and sacrifice for the love of country. Another thing to keep in mind is that the neighborhood is picturesque, but not touristy, so take snacks or stop by the ice cream cart that is often parked on the trail just below the last leg of the

climb (and starting this year, food trucks will also be allowed to park in the Navy Yard). The Freedom Trail continues back to Boston, but it might make more sense time and traffic-wise to double back through the Charlestown Navy Yard and return by ferry to downtown. The park right by the ferry has a playground and spray pool, and even a low-key Dunkin Donuts in the office building across the street.

 Long Wharf, next to the Charlestown ferry dock, is a hub of boat travel to different places around Boston. If you board the commuter ferries to Salem and Provincetown, you’ve already pretty much given your day over to those sites. If you are looking instead to take a short break from the sweltering summer heat without getting stuck in beach traffic, consider a full or half-day trip out to one of the Boston Harbor Islands from the Long Wharf terminal. Georges Island preserves the remains of the 19th-century Fort Warren (named for Joseph Warren!), while Spectacle Island has a public beach where swimming is permitted. As they are only accessible by boat, both islands enforce a carry on-carry off policy, but restrooms are provided and (usually) a snack bar: the ferries also have food on board for purchase. The best part is that National Park rangers and other expert staff are on site to provide excellent visitor services including activities for younger children.


If your family elects to stay on the mainland, Long Wharf is where the Norman B. Leventhal “Walk to the Sea” trail begins. This self-guided itinerary is one of my favorite historic trails in Boston because it is marked by illustrated panels mounted right on the sidewalk. A number of these are grouped together on Long Wharf. Hopefully you can steal a moment or two to study them, especially the one that shows changes to the Boston shoreline over four centuries. You might very well end up on Long Wharf at a time it is partly submerged - the puddle of all puddles! Speaking of puddles, if it is raining too hard to stay outdoors for very long, the New England Aquarium is right on the next wharf (Central), and a whole fleet of covered trolleys and Duck Boats depart from the bottom of Long Wharf. These are ways to stay high and dry for at least a couple of hours. I’ll get to the Children’s Museum in a bit.


From Long Wharf, it is about a five minute walk to a number of sites along the Freedom Trail (Faneuil Hall and the Old State House, plus the statue of Sam Adams I remember so well from childhood). While you’re here, be sure to pick up some free maps and historical brochures at the NPS Faneuil Hall Visitor Center on the ground floor of Faneuil Hall. If there’s time, take one of the ranger-led tours of the building or download the free audio tour. On weekdays until the early afternoon, the Ancient and Honorable Artillery Company Museum on the fourth floor of Faneuil Hall is also open to the public, and has a lot of interesting military paraphernalia that, like it or not, often gets kids’ attention. 


Across the street from Faneuil Hall and Dock Square  is the much larger Boston City Hall. It is all massive and modern, but don’t overlook the fully accessible playground on the side of the complex facing the Boston Public Market and New England Holocaust Memorial. It’s what locals now call “Cop Slide” Park, and while your kids are clambering about, you can take a moment on your phone to learn why. 


The Paul Revere House is also not far from Long Wharf if you opt for a North End detour. Like the Freedom Trail’s Bunker Hill loop, the North End part also gets you out of the big city setting and into a neighborhood - specifically, one of the oldest surviving urban residential enclaves in the entire country. I have found that younger children are very open to roaming the historic burying grounds along the trail, and the North End has one of these on Copp’s Hill. This particular district also has a number of historic churches of different denominations, which are definitely worth checking out for their architecture and furnishings, both inside and out (particularly the Peace Garden attached to the church of St. Leonard of Port Maurice and garden patios next to Christ Church, the “Old North” of Paul Revere fame). 


Almost the entire North End neighborhood is now bordered by the long strip of parkland known as the Rose Kennedy Greenway, and each one of its parcels is distinct. The Rings Fountain and North End Park sprinklers are meant to get people wet, so if that’s the last thing you need to deal with, or you just don’t feel comfortable letting your kids run around in close proximity to traffic, head over instead to the Tiffany Foundation Grove, home of the Greenway Carousel. Its hand carved characters represent local animal species (rats, pigeons, and seagulls excepted). The Greenway provides food trucks in season, and there are year-round food services in the nearby Boston Public Market, where seating is much less formal than in a restaurant and you can mix and match cider donuts with other local treats: for grownups, this could be a George Howell coffee (he invented the Frappuccino, but you’ll have to order it from him as “the Original”).


If you continue on the Boston Harborwalk southward from Long Wharf, you are taking a very scenic route to arrive at one of Boston’s ultimate kid meccas. On the way, you will pass boat docks, curious public sculptures, and possibly the largest flag display in all of Boston at Rowes Wharf (usually American, but Irish on St. Patrick’s Day). If at all possible, stop by James Hook & Co. for the fishy aroma and the Boston Harbor Hotel to see the historic map collection in the lobby (also a bathroom break).


Soon after entering the Fort Point Channel, the Boston Tea Party Ships and Museum come into view, as well as a 40-foot tall Hood milk bottle marking the entrance to the Boston’s Children’s Museum. These places, along with the undulating and climate resistant Martin’s Park, can capture a young child’s attention for a good amount of time. Nor is anyone likely to go hungry. As you might expect in a waterfront location, several nearby eating establishments specialize in seafood, like The Barking Crab, but there are also burger and taco joints in the nearby Seaport district, as well as many different foods to try in Chinatown. 

You’ll come across many other iconic children’s experiences in Boston (like the Swan Boats, Charles River Esplanade, and Boston Common with its overly attentive squirrels). The real plan is to make Boston part of your own history. For that, your kids will lead the way.  


In addition to the tour company services already mentioned, a great child-friendly tour of the Freedom Trail is the one-hour “Boston by Little Feet”, specially designed for children ages 6-12 (I occasionally lead these tours). The Freedom Trail’s “Walk into History” tours with guides in 18th-century costume are popular with school groups and families. Another Freedom-Trail focused experience is Walking Boston’s private family tours. Tour companies and individual guides can also tailor private tours to the needs of families with young children. 

About the author. Jessica Dello Russo, Ph.D., is a Boston-based author and historian. She is executive director of the North End Historical Society and regularly leads tours of Boston and other parts of New England. Follow on Twitter.

We would like to thank our friend and colleague Dr. Jessica Dello Russo for sharing her insightful experiences and suggestions about touring Boston--particularly for kids! Jessica shares our belief about educating young children to learn more of our collective past. We encourage you to visit Boston and learn more about where our American Revolution began! Thanks, Jessica...

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