The Freedom Trail: A Walk Around Old Boston

Boston, MA: June, 2021

Continued from: Fenway and the Finish Line: An Evening in Modern Boston

A quarter of a millennium before my visit to Boston, the seeds of discontent had blossomed into rebellion in what was then a colonial seaport. Maps from that era are hardly recognizable as the same city. What we now know as the Boston peninsula was then a turtle shaped near-island connected to the rest of Massachusetts by a tiny spit of land no more than fifty feet across called the Neck, which offered a huge strategic advantage but little room for growth. The Back Bay was a swamp, much of the land between Beacon Hill and the North End was beneath the Charles River, and Boston Common was on the waterfront. If I were to somehow wake up in 1770 in the exact location of my bed at the Yotel, I would be treading water a half-mile out into Boston Harbor. You don’t need to know the slightest about the city to know which parts are original and which was infilled during the last century or so, as a quick walk around the downtown will oscillate between architecture of the past and the present. Cross Congress Street to the north and immediately the land is flat, gridded, and littered with glassy high-rises. The same occurs at other boundaries around the city, and one can practically trace the old coastline without consulting the map.

I knew the Freedom Trail was a lengthy walk so I began my day early, arriving at the little kiosk on Boston Common around seven in the morning. The sun had been awake for a while as it happens on the east coast in June, and the locals and visitors to Boston likewise got to an early start, the streets busy with commuters and shutter clickers.

Compared to other major city central parks, Boston Common leaves something to be desired, its spacious grasslands and few tree rows looking a bit barren and underappreciated, a direct contradiction to the neighborhoods that surround it. Paths crossed at acute angles like a campus green and park benches sat empty across from each other. The park wasn’t unkempt, just a bit bland, but still I appreciated the history. From a puritan era cow pasture to a British camp during the Revolution to a public meeting ground, the Common has had many lives in its nearly four hundred years of existence. In the current era, it essentially acts as a cut-through between neighborhoods and as the beginning of the Freedom Trail. In a way, its lack of ornateness is a proper tribute to its roots as a simple public green, though it probably smelled a lot less of weed when John Adams was wandering around.

The Freedom Trail is marked by two columns of red bricks placed into the ground and snakes its way for two and a half miles, passing by most of central Boston’s most important locations. For the most part the trail is easy to follow, but every so often, when it crossed a street or a road closure forced a slight detour I had to consult the interactive map on my phone.

Upon leaving Boston Common, the red bricks heads right up the stairs to the Massachusetts State House, which overlooks the park but was unfortunately closed for staffing issues, something I would repeatedly come across while walking the trail as I had unwittingly chosen an unpopular day of the week to do so. Not far from the state house is the Granary Burying Ground, the first in Boston and the resting place for folks like Paul Revere, John Hancock, Ben Franklin’s parents, Crispus Attucks, and other victims of the Boston Massacre. Centuries old dome-shaped headstones stretch out in rows beneath towering linden trees and are hemmed in by brick buildings. I perused for a bit, just as fascinated by the unknown names as I was those from the early chapters of an American History book. Some of the markers, like a column dedicated to Paul Revere or a rock for Samuel Adams were covered in pennies for reasons I wasn’t sure. A nearby maintenance worker with a weed whacker revved it up and I made my exit.

I passed the Old South Meeting House, and also the Old State House, in front of which a circle commemorated the exact spot of the Boston Massacre and a rainbow bunting hung from the second story balcony. Looking down Meeting Street to where a replica of Hancock’s ship floats tethered to a bridge beyond the interstate exit ramp, it was tough to imagine the mob of angry Bostonians storming down the hill do turn the harbor into tea. 

The early morning clouds began to dissipate and what remained was a spectacular sky of soft cyan, the kind that only seem to appear in early summer. I walked briefly through Faneuil Hall Market but much of it had yet to open for the day and I figured I would come back after finishing the trail and look around some more. I looked down at my phone a few times, as I was expecting a text from Lauren at any time that day regarding a job she had applied for that would help determine where we would be living when autumn came around. For as much as I enjoy solo traveling, I wished she could be there and I knew she would enjoy this walk through a new city and away from the humid and cicada swarmed Midwest. 

I took a break with a sandwich and a cortado at a coffee place that was tucked into a microneighborhood between downtown and the North End, an area that had skinny cobblestone streets and looked like Diagon Alley. The chairs sat one to a table, all facing the same direction like the solo row on a small jet. I dug into the croque monsieur and looked over the old newspaper clippings beneath the tabletop lacquer. The song American Cliché by Finneas played ambiently over the speakers, and when he sang about how he was “missing a girl in a French café” I couldn’t help but relate despite the fact that the place was only French by design.

Back outside, I followed the red brick path toward the North End proper, but not before crossing over one of Boston’s other successful revolutionary ideas. I-93 used to hook across the peninsula on an elevated bridge, bisecting neighborhoods and generally adding a degree of midcentury ugliness to the whole enterprise until the ‘Big Dig’, completed in 2007, was completed as the most expensive highway project in US history. Land was carved out and the road was covered by a string of parks, with benches, playground equipment, beer gardens, and green space, a bit like if the New York high line were on street level. As I crossed through the greenway, which is easily visible in satellite view, an emerald squiggle like the Chicago River in March, I thought of a similar place at home in Cincinnati that would do well to follow Boston’s lead. The interstate through downtown is already dug and it just needs capped. Seems like the hard part is finished.

The North End is now known for Italian food and gelato stands as much as for its revolutionary history. Restaurants lined Hanover, their seating spilling out over the sidewalks and into former on-street parking spots, protected by faux-iron fencing and construction barriers. Umbrellas popped open as business lunchers sat down with glasses of Chianti and servers brought menus from the front doors to the new front porches. The air smelled pleasantly of basil. As cities worldwide relaxed zoning to allow eateries in dense areas to put tables out front, a degree of streetside liveliness was imbued that I hope remains now that things have begun to normalize, though this of course would require local beaurocracies to admit that sometimes less fussing is ideal so that obviously will not happen. 

Just off of Hanover is the Paul Revere House, a two story structure wedged in between taller buildings of Victorian origin. With its heavily slanted roof, diamond windowpanes, and sepia tone, the house looked more like what you would expect to find in middle England as opposed to colonial Massachusetts. Even the sign protruding from the side paneling looked like it should have read Ye Olde something. Unfortunately, this too was closed, and I followed the dual rows of brick deeper into the neighborhood. Not far is the Old North Church with its towering steeple light of ‘One if by land, two if by sea’ fame. A shaded brick courtyard sits in front with a statue of Revere on his horse before the midnight ride to Lexington and Concord, then semi-distant towns, now exurbs of Boston from which modern commuters follow the storied route by day.

I crossed the bridge into Charlestown and explored the neighborhood, which curiously reminded me of my own several states away if one could overlook the difference between Federal and Italianate style townhomes. Even the street names were similar. It is heavily residential, even along the brick-lined main way, and the cross streets slope gently upward, hemmed in by rows of tall, skinny homes that stairstep in turn. At the top is the Bunker Hill Monument, which is actually on Breed’s Hill. The obelisk, which looks a bit like an unsharpened Washington Monument, towers over Charlestown and marks the spot of the early Revolutionary War battle. The grassy park is about the size of one city block and all sides slope down, allowing a 360 view of the neighborhood.

It was here that the Freedom Trail diverged into several forks, all ostensibly heading back to downtown Boston. This wasn’t shown on the online map, but as all roads led downhill, I picked one and knew I would hit water eventually. I ended up near the USS Constitution, which floats in the Navy Yard near the mouth of the Charles River. Old Ironsides as she was called, is younger than the Revolution by a couple decades, first called for duty during the Quasi-War with France and most known for being used during the War of 1812. It looks like what you’d think of when you think of an old ship except the wooden hull is painted black.

I had technically completed the Freedom Trail at this point but still had to backtrack so in truth my Boston flaneur was only half done. I reversed course across the bridge and through the North End, again smelling pasta and watching enviously as al fresco diners dipped tough-crusted bread onto small plates of oil.  Well past lunch and with about 40 thousand steps already taken, the neighborhood was all the more enticing on the way back, though after perusing a few menus and seeing the outdoor seating areas becoming increasingly stuffed like ziti, I silently acknowledged that the market would be a simpler and more cost-effective venue for a solo meal.

Faneuil Market had come to life in my absence. Nearly every table in the large plaza  was taken and at each corner was a musician: a guitarist singer/songwriter, a duo playing the jugs, etc. Inside was a similar bedlam, and the food stand proprietors all seemed to be having a profitable day, their stoves sizzling as they attempted to keep up with their lines of several dozen. Still in the mood for Italian, I got a couple of slices of thin crust pizza, not least because it was the shortest line, and ate outside while listening to the jug guys. It had been a spectacular day and it was only just after two. 

Lauren called just as I was finishing up and I walked back over to the greenway to answer so that I could hear over the rapping of drumsticks on glass. She told me that she did get offered the job that would keep us at in Cincinnati for a while longer. I was ecstatic for her and loudly expressed as such while sitting at a table across from the North End, causing the phone-nosed couple at the next table to look at me funny before digging back into their noodle bowls. I wished Lauren were there, but knew the important reason she was not. We talked for a bit as I made the long way back to the beginning of the trail and back into the central business district.

I wasn’t sure what to do to kill time so I perused a map store. The owner was super friendly and very interested in helping me as I looked around at old maps of Boston from when it was practically an island and original plots of the state of Massachusetts. As soon as I noticed the cheapest items in the store were several hundred dollars, I stayed long enough to be polite then slowly ambled back to the Yotel.

The Freedom Trail had made me want to rewatch HBO’s John Adams, the one where Paul Giamatti plays our bald beneath the wig second president, and so that’s how I spent the late afternoon as the sun disappeared and a rain swell moved through. The first episode focuses on the Boston Massacre and watching the reenactment in front of the Old State House was more interesting having just seen it in person. Outside the window of my room, one which I still contest isn’t small enough to make the miniature size its focus, a concert at a beer garden got soaked. I had bought some local beer to take home before realizing my “cabin” didn’t have a fridge, so I asked the front desk if I could put it in the main one downstairs, as the website indicated I could. Instead, a few moments later, they brought up a tiny portable one that was pastel pink and looked like if Nickelodeon designed a hotel safe. All but one of the beers fit inside, an easily solvable problem as I queud up the second episode of John Adams and waited for the rain to abate.

The fickle New England weather soon switched allegiances again and the evening was beautiful. I picked up a banh mi and walked along the new seaport boardwalk past outdoor pilates classes and brand new apartments with eaves that bent and curved beneath grassy living roofs and looked like they were built in a hipster Whoville. It was incredibly pleasant, walking through this area that was underwater during Adams’s time and an industrial wasteland as recently as Clinton’s. The renewal was done far more aesthetically tasteful than in many places that boomed during the early part of this century. The esplanade stretched for miles and despite all the walking earlier, I followed it as the sun slowly set directly over the modern Boston skyline. The rain had wiped away the humidity and what remained was a perfect summer night, one of the shortest of the year. The dense low-rise of the North End peeked out behind downtown, and if I covered up the high-rises with one hand I might have an idea of what it would have been like to come in from the harbor after a day at sea during the city’s early days, but at that moment, a large yacht left the port of Boston, heading east, while the sun finished reflecting off the glass of the tallest buildings and sank behind the peninsula. History and modernity, side by side.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: