Revolutionary Monuments, Missing the Ship, and a Surprising Bit of Inspiration on the Freedom Trail

Bostonians do not, as a rule, walk the Freedom Trail. It’s the same as New Yorkers who don’t ascend the Empire State Building or Los Angelenos who don’t hang out in front of the Hollywood sign. We’ll do it—maybe—if friends are in town and have nothing to do.

To break the pattern, Flyby decided to embark on the 2.5-mile historic tour of Boston to experience our (well, neighboring) city from the point of view of an outsider—so you don’t have to.

The Freedom Trail is a path that snakes through downtown Boston from the Common to Bunker Hill, passing 16 historic locations. Of course, you can sign up for an official tour led by a guide in traditional colonial wear and inevitably a thick Boston accent, but it’s pretty easy to walk the trail by yourself too. The visitor’s booth on Boston Common sells maps for $3, and that provided me with enough guidance for the trek. Plus there was always Google to help me out.

I don’t want to spoil the ending of the American Revolution, so I won’t go into too many specifics, but here’s a brief rundown of the best historic locations and what to avoid.

The first stop on the tour after Boston Common is the Massachusetts State House. While I appreciate a nice gilded roof, it does make you question where all our tax dollars are going.

After Park Street Church comes the Granary Burying Ground, which is a tourist hotspot even for those who aren’t walking the whole trail. Bostonian legends like Paul Revere, John Hancock, and, inevitably, Tom Brady are/will be buried here.

From there you go to King’s Chapel, the first Unitarian Church in America. The chapel, unlike many of the landmarks on the tour, mentioned its “complicated” relationship with slavery. While the family of Charles Sumner—the senator who was brutally beaten for his anti-slavery stances and a member of the Class of 1830—sat in the 74th pew, the chapel never took a firm stance on slavery.

Though the Freedom Trail mostly focuses on well-known revolutionaries and glosses over other Americans, there is a Black Heritage Trail that offers free guided tours and tells the story of early America from a different and necessary perspective.

The next few stops were old meeting and state houses. One dad, after noticing that a meeting house had an entrance fee, turned and said to his children, “We got it: It’s a room.” Flyby approves of his attitude.

We then stopped at the historic Sephora on North St. to thank the Founding Fathers for the blessings they have provided to their posterity.

If you really wanted to dive into the colonial experience, there are plenty of old taverns and pubs around where you can sing the national anthem until you’re red in the face. Instead, I, like any good millennial, went to the restaurant Saus, best known for its french fries and sauces.

It was about here, more or less halfway through, that we discovered a literal brick trail that leads you through the monuments. It’s like Google Maps but, you know, tangible, visible, and physically in the ground.

The next few stops were houses and graveyards, again. I passed the U.S.S. Constitution without really noticing the giant ship because we were too preoccupied with our fear of bridges, but you could spend at least a few hours just visiting the museum there.

The last—and my favorite—stop was Bunker Hill. While misinformed pseudo-Bostonians like pre-Freedom Trail me might mistake it for a replica Washington Monument, the 221-foot Bunker Hill monument contains quite a bit of history.

The Battle of Bunker Hill was one of the bloodiest fights of the American Revolution, leaving over 200 dead and more than 800 wounded. The monument, which you can walk up, stands to honor those fallen in the first major battle of the Revolutionary War.

Be warned: Climbing up that monument is hard. It’s 20 flights of stairs, which is a lot of stairs. It is also a bunch of sweaty people, no windows, and very little light. If you’re really craving a view of Charlestown, then climb away. But I left as a hot sweaty mess who Ubered home.

All Bostonians (and those who live nearby) are lucky to live in a place where you can shop, view history, and explore most of the city in just about two and a half hours. I think I saw more of Boston on the Freedom Trail than in an entire childhood spent in Cambridge. Even if you don’t like history, it’s worth following the brick trail for a nice view of the “Walking City.”

I will say there was something moving about the Freedom Trail. At a time when Americans can’t agree on even basic facts, the Trail takes you back to a period when (almost) all Americans were united in fighting a common enemy—and, spoiler alert, we won.

We’ve grown by 37 states and righted many wrongs since 1775, yet the ideals that animated the men who died at Bunker Hill seem to have either been forgotten or disregarded. George Washington, John Hancock, and the other wig-wearing men of the 18th century were far from perfect, but they fought for a common good on which this country is built. That’s something—even if you’re a lethargic Harvard student—that’s worth walking for.