Old State House, Freedom Trail, Boston, New England

Finish Lines, Fenway and the Freedom Trail: A Family Guide to Exploring Boston, Massachusetts

“Boston isn’t a city, it’s a family.”

-Chad Finn-

We have an affinity for historical cities.  There is something captivating about the architecture, character and deep rooted pride of a destination that carries with it the vibrancy of the past.  Boston, Massachusetts, is a culmination of curves and clean lines, as a 19th century church reflects its gothic mirror image into the blue tinted glass of a 60 storey skyscraper.  Narrow alleys run parallel to grande promenades and historical row houses display collections of modern art and fashion.  Boston is a blend of exquisite intricacy, delectable dishes, waterfront serenity, a bustling market life and hard core sporting fans.  And that accent.  So is Boston with kids a good idea? YOU BET!!

John Hancock Tower and Trinity Church, Boston, Massachusetts


One of the largest hurdles in travel planning can be deciding where to stay.   So how about Boston with kids?  What area is safest?  What location offers the best proximity to major sights?  Is there a metro nearby?  Restaurants?  Shopping?  When it comes to Boston with kids, or as a couple, we HIGHLY recommend the Back Bay area as a home base.   Drawing 10’s of millions of visitors each year, Boston is generally an expensive city to visit, especially during the months of June-November.  The cost of a hotel in the core of the city is among the priciest in the US, but we consider it worth the expense for one major reason:  walk-ability.  We chose to stay at the Fairmont Copley Plaza, and it was an investment in ensuring our overall experience was top notch.

Why stay in Back Bay?  This is a place you could easily spend your entire time in Boston exploring.  A protected historic district and famous for the exclusive row houses of Commonwealth Avenue, Back Bay was once a literal bay.  Since a massive filling project in the 19th century, it is now considered one of the best preserved examples of 19th-century urban design in the United States, and one of the most expensive residential neighborhoods in Boston.

Row Houses, Commonwealth Avenue, Boston

Running along the Charles River, opposite Cambridge, the area is home to the Copley Square Farmer’s Market, Boston Public Library, numerous historically significant churches and the prestigious Boston Marathon finish line.  Those looking to shop can choose from the range of stylish individual boutiques and high end fashion houses of Newbury Street.  Foodies can indulge in a multitude of creative cuisine options and even the most expectant traveler will have his luxurious requirements met by the upscale array of accommodations. Back Bay is quite simply the heart of Boston, its glamorous arteries beckoning you to stroll and connecting you to the best experiences the city has to offer.


Atlantic Fish Company, Boston, Massachusetts

For most travelers, food is an integral part of the overall destination experience.  We’ve learned that locals are one of the greatest assets in sourcing recommendations.  So where to start?  If there is one place we recommend visiting during your stay, it is the Atlantic Fish Co. on Boylston St.  This popular establishment has been serving up fresh seafood on a “printed daily” menu since 1978. It was so good we ate there two of our five nights in downtown Boston.  **Make a reservation to avoid disappointment!

So what else makes the list of local recommendations in the area?  Start your day by grabbing a coffee from Wired Puppy.  For breakfast, hit up one of the boutique gourmet stops in Beacon Hill such as Paramount or Tatte Bakery and Cafe.   Curb your sweet cravings with an artisan cupcake from Georgetown Cupcakes.  Indulge in an authentic east coast lobster roll or an amazing raw bar at Saltie Girl.  For those looking to enjoy a place where “everyone knows your name”, the pub that inspired the hit sitcom Cheers can also be found in Beacon Hill.


The 2.5 mile (4 km)  Freedom Trail is perhaps one of the most popular attractions in Boston, historic or otherwise.  It is a perfect family-friendly experience in Boston with kids.  The path winds it’s way through downtown Boston, passing 16 significant historical locations and landmarks.

Old State House, Freedom Trail, Boston, Massachusetts

Over 4 million people annually follow the iconic red line that traces 250 years of history.  The walk begins at the 44 acre Boston Common, America’s oldest public park, established in 1634.  Here you can choose to follow the trail for free (detailed maps can be purchased at the beginning) or you can choose from several informative tours.  Sites range from graveyards and churches, to the State House and the Old South Meeting House, well known for being the site where the Boston Tea Party began.  The Old State House stands as the oldest public building in Boston, having survived the Boston Massacre, Revolution and fire.  Referred to as the ‘home of free speech’, beautiful Faneiul Hall leads itself to a massive market.  Continue on to view sites such as Paul Revere’s House, the USS Constitution and finish your journey at the Bunker Hill Monument.  Even for those who are not history buffs, the walk is picturesque and the architecture alone makes the trek well worth it.

TIP: The city’s harborfront is a very short walk from Faneuil Hall and Market.


Boston Public Gardens, Boston

Established in 1837, this serene slice of greenery is hailed as America’s first public botanical garden.  Part of the “Emerald Necklace” system of parks, Boston Public Garden is known for its summertime swan boat rides.  The gardens are home to numerous fountains and monuments, including the George Washington Statue, a 4 acre pond, exotic imported trees and over 80 species of plants.  If you are exploring Boston with kids, children will love both the real swans who call this park home, as well as the popular “Make Way for Ducklings” installation, a happy bronze family featuring Mrs. Mallard and her ducklings.


There is something special about a city with sea views.  Landing at Boston’s Logan Int’l Airport is a visual feast, as the downtown skyline collides with the waters of the Atlantic.  Boston Harbor is a natural harbor and estuary off of Massachusetts Bay. Over the past three decades, roughly 40 miles of waterfront have been developed into a near continuous linear park, the Boston Harborwalk.  The harbor is a great place to catch a ferry, take in the city from the water, and visit sites such as Spectacle and Georges Islands. 

 The Charles River is another extremely picturesque spot to enjoy a water view.  The waterfront promenade made for an enjoyable walk between our hotel and the Museum of Science, offering scenic views of Cambridge, MIT, Longfellow Bridge and the many sailboats enjoying the calm of the sunshine.

The Charles River, Boston, Massachusetts


Boston is a seriously spirited sports city with a deep rooted legacy of legends and championships.  Year round, fans head out clad in team colors to cheer on the Celtics (basketball), Bruins (hockey), Patriots (football) and the Red Sox (baseball).  They drink beer, sideline coach, celebrate, suffer and sing along to the 7th inning rendition of ‘Sweet Caroline’.  If you follow us regularly, you know we are a family that loves live events, and I can honestly say that our experience alongside some of the most fanatical folks in North America was a privilege.

The entire reasoning behind our trip to Boston was to see the New England Patriots play at Gillette Stadium.  At 29 miles southwest of downtown, Patriot Place and an NFL kickoff are definitely not a “walk-able” experience, but as this is often a highlight and bucket list item for travelers, it deserves mention.  We chose to stay directly onsite for several nights around the game, and I would highly recommend doing so.  You can read all about our Patriots experience HERE.

FENWAY: America’s most beloved Ballpark.  Since the day it opened in April of 1912, Fenway Park has been home to the Boston Red Sox, but it has also been home to generations of families gathering in the name of baseball.  The park may be the oldest and fourth smallest in the league, but has seen some of the biggest home runs in history and houses some of the most passionate fans in the world.

We had the extreme good fortune of the Red Sox making the post season while we were in Boston.  An experience doesn’t get much better than a chance opportunity to see such icons as the Boston Red Sox take on the New York Yankees in the NLDS at Fenway Park.  You don’t even have to appreciate the sport of baseball to understand the significance of what you are witnessing.  We were able to secure tickets in the Coca Cola Pavilion with excellent views of the Green Monster and unobstructed views of the entire field.  It was perfect for our family.  Did we pay though the nose for resale tix?  Yes. Was it worth it.  ABSOLUTELY. 

For the record, the Patriots went on to win Superbowl LIII against the LA Rams and the Red Sox went on to win the World Series against the LA Dodgers.  Just sayin’.


Founded in 1848, the Boston Public Library is a masterpiece of architecture.  It contains roughly 24 million volumes and electronic resources, including 1.7 million rare books and manuscripts, making it the third largest public library in the United States.  Making a point to walk quietly along the corridors, passed the lions guarding the grand staircase and into the Bates Reading Room of the McKim Building, dozens of faces working diligently, is a highlight for anyone with even a slight literary appreciation.  Follow along history until your reach the stunning, Italian inspired courtyard in the centre, designed to look like an arcade in the Palazzo della Cacciatella in Rome.


When planning our Boston with kids adventure, we asked fellow travelers and locals about the best activities for families.  Most highly recommended was a Boston Duck Tour.  So just what exactly is a DUCK?  It is a WWII style amphibious landing vehicle….and a ton of fun.  It is a unique spin on your average city tour, and ideal for all ages.  We began our fully narrated, 80 minute tour at the Museum of Science and passed roughly 3 dozen specific points of interest before heading into the Charles River for a pleasant cruise.  Duck Tours depart frequently from 3 separate locations (Prudential Centre, Museum of Science and the New England Aquarium).

Boston Duck Tours


A fantastic stop that will make the kids happy and keep the parents interested is the Boston Museum of Science.  It features a revolving schedule of temporary exhibits, IMAX films, and Planetarium shows, as well as more than 700 interactive permanent exhibits.  Make sure to hop on the “Thrill Ride 360“, a full motion simulator that was an absolute highlight for Littlest B.  A favorite exhibit of ours was the ‘Lightning’ show, a live presentation of indoor lightning bolts produced by the world’s largest air-insulated Van de Graaff generator (warning to those with noise sensitivity).

Like all great cities, Boston provides immediate gratification with its charm, passion and architectural blends, but requires time to fully appreciate the sheer scale of such diversity and history.  The above mentioned ‘Boston with Kids’ experiences I share with you because they were highlights for us.  There are so many opportunities we simply did not have time to explore and partake in, but it is the perfect excuse to return.  I went to Boston to watch a football game.  I left in love with river views, row houses, clam chowder and baseball.  Cheers Boston.  Next time you need a World Series title or shiny Superbowl ring, you know where to find us.

Go Pats!



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18 thoughts on “Finish Lines, Fenway and the Freedom Trail: A Family Guide to Exploring Boston, Massachusetts

  1. Oh my gosh! Your hotel was beautiful. We haven’t visited Boston yet but we’ll definitely seek out the back bay area when we do. We’re originally from an island in the Atlantic so I’ll definitely be trying the Atlantic Fish Co. The food looks delicious!

    1. Yes, The Fairmont Copley hotel was definitely the cherry on top of a perfect trip! The food was incredible, such variety, but you can’t really go wrong with fresh Atlantic seafood for sure!

  2. Great guide guys, we visited back in 2011 on day trip from NYC back when we were students. It was a bit of a whirlwind and it was in the middle of winter too so it was so cold!! But we fell in love with the city and always wanted to go back for a proper visit in warmer weather!! Hopefully we can do that in the next few years with a few more ideas of places to see now!

    1. Thanks for the kind words! I think even a whirlwind stop is a good enough taste to understand what an incredible city Boston is (even in the cold), and I hope you guys get a chance to explore again in the future!

    1. I LOVE the walk-ability factor of this city! So many incredible sites are so easy to get to, especially in a downtown core that is a bit more difficult to navigate by rental car. And I completely agree on the cleanliness and the green factor, they both really stood out to us as well!

  3. Is the Longfellow Bridge measured in Smoots? We (well Jenn) is going to Boston this summer so I’ll pass on the Freedom Trail. That looks like a super easy way to see the heart of the city. Solid post!

    1. I imagine it is fantastic year round (as Canadians we’ve learned to enjoy all seasons) but yes, the warmer months would making walking around and the other outdoor activities much more enjoyable for sure!

  4. I did Boston a few years ago, but didn’t stay nearly as long as I should have. I’m looking into family friendly places to visit that are easily accessible from NYC, so I’m glad I read through your post! There is so much more to do here than I ever would have imagined and I’m really looking forward to checking out things like the Harbor Walk and the Public Library (places I would have never considered looking into!) Great post!

    1. Thank you for such kind words! We tried doing our research before we left, but had no idea just how kid friendly and spectacular a city Boston would truly turn out to be. We had so much fun watching the action at the library out our window at the Fairmont, they were filming scenes for “Little Women” with Meryl Streep and Emma Watson!

  5. Love Boston … called it home for a number of years and go return regularly. Good choice on staying at Copley Place. Great hotel and very central. I also love the fact you pointed out the public library. So many people overlook seeing public libraries when they are traveling and yet so often, they are such amazing places to visit.

  6. The city that smells of cinnamon! Or it has when we’ve visited. Your hotel looks gorgeous, and I love how you did so many of the best things on your trip. We missed out the library sadly, but I can remember so many bits of the waterfront and the Freedom Trail. I can’t wait to go back!

  7. I took a short layover with only a night stay in Boston so could not see enough. Boston public garden and waterfront looks beautiful and worth.

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