What I learned walking the Freedom Trail as a recent American citizen

In the 12 years that I’ve lived Boston, I’ve checked off plenty of iconic attractions: I went to a Red Sox game at Fenway, I made way for ducklings in the Public Garden, I’ve gotten a cannoli in Little Italy and I have rubbed John Harvard’s toe at Harvard University. But there is one touristy thing that I kept evading — walking the Freedom Trail , a historic pathway that winds through the city, connecting the landmarks that tell the story of how the American Revolution began.

There was a reason for my feet-dragging: I have a hard time connecting with history, no matter the country or time period. I tend to get lost in the sequence of events and the unfamiliar cast of characters. In my history classes throughout high school and college, I was disoriented, confused and overwhelmed much of the time.

American history felt especially foreign to me. Growing up in Ukraine, I learned about Benjamin Franklin and Honest Abe. But these historical figures felt more like revered symbols than flesh-and-blood people.

Still, as a recently naturalized American citizen, I wanted to revisit these stories. After all, American history is now becoming my history, too. So I booked a tour of the Freedom Trail, one which promised to be “the most comprehensive walking tour of the Freedom Trail available.” What I found there changed how I see American history — and that of my own country.

‘Creative rerouting’

As I began my adventure on a recent Friday morning, it became clear that the day was not going to go as planned. The train was packed with Celtics fans who were heading into the city to celebrate their NBA championship. “Our guides may have to do some creative rerouting,” said the text that I received from the tour company. I was absorbed into their revelry as I was pressed into the raucous crowd. There were clover-shaped earrings, green jerseys and perspiring armpits. I’ve never been on a train with happier riders.

When I emerged from the underground, the Boston Common was a sea of green. The smell of hot dogs wafted from a nearby stand. I walked toward the designated meeting spot — behind the Robert Gould Shaw Memorial , a bronze bas-relief sculpture facing the golden-domed State House . The memorial commemorated one of the first Black volunteer regiments in the Civil War, led by Col. Robert Gould Shaw.

Expecting to see a guide decked out in colonial attire, I was surprised to be greeted by Julie — or Jules, as she introduced herself — a young woman wearing red lipstick that matched her shorts and cat-eye shades, and sporting a few tattoos. Our group was me and a family from Atlanta, who had just gotten off a cruise to the Bahamas and Maine and were stopping to tour the attractions in Boston.

Jules started out by grounding us in the place. Back in the 1600s, the Boston Common was not exactly as thrilling as the sports revelry unfolding before us. It was a rough, uneven expanse with small hills and wetlands, and was used as a grazing pasture. Now a lush park with a playground, the Common was later the backdrop to the public punishments conducted by the Puritans — whippings, executions and the locking of offenders in the pillory. Near the playground, where I’ve taken my kids dozens of times, is a plaque that says it was once the site of “the great elm,” also known as the “hanging elm” on Boston Common. Later on, during the occupations of Boston in the 1760s and 1770s, thousands of British redcoats used the park as a parade ground and encampment.

In a mansion that used to sit on the hill where the golden-domed State House is now perched, John Hancock met with Samuel Adams and Paul Revere to concoct plans leading up to the revolution. Hancock’s mansion was later demolished and replaced by two fashionable town houses. The abutting Beacon Hill neighborhood is today one of the poshest in the country; a home there recently sold for $28 million .

To get to our next landmark, we elbowed our way through the crowd of fans, who by then were sipping drinks from green cups. We dove into the Park Street train station, where Jules informed us that Boston’s subway system, built in 1897, was the oldest one in America. ( Take that, New York!) We walked through the tunnel and within minutes were strolling past Gap and T.J. Maxx, where occasional shoppers intermingled with revelers.

From the shady spot between the Walgreen’s and a bronze monument commemorating the Irish famine, Jules pointed out a black building on Milk Street , the site where Benjamin Franklin was born, and the school where he studied for two years, before going to work as a soap and candle maker at age 10. The person I’ve read about dozens of times was now tied to a specific place, and this new context made him more real and interesting.

We were surrounded by Colonial architecture, Jules noted, including the small 1718 brick home with original hand-blown glass window panes that now housed a Chipotle. Across the street towered the Old South Meeting House , which was the hub of the resistance against the British and where in 1773, about 5,000 people gathered to debate the tea tax after failed negotiations with the royal government. It’s where Samuel Adams (who, I’ve learned, did not drink, despite the namesake beer brand) gave the signal to start the Boston Tea Party at Griffin’s Wharf, just a few blocks away from the meeting house. King George III was, of course, furious with Boston’s colonists, Jules told us, and sent 4,500 troops to occupy Boston.

For all my gaps in history knowledge, the American story of resistance, the desire for self-determination and the fight for national identity resonated with me.

Pursuit of a grand objective

I grew up in Ukraine, where we had our own revolutionaries who fought for independence from the Russian and Austro-Hungarian empires and others who wanted to subjugate the Ukrainian people and their land. But in my homeland, that fight for freedom is still ongoing as civilians and soldiers continue to die from Russian missiles and bombs. These tragedies serve as a daily reminder of how elusive freedom can be; freedom is a gift and a privilege that should not be taken for granted.

The breeze from the wharf provided welcome relief from the heat while our group paused near the Old State House , where in 1770, British soldiers fired into a crowd of colonists, killing five men, a pivotal event called the Boston Massacre that galvanized colonial opposition to British rule. Six years later, in 1776, a copy of the Declaration of Independence was read from the balcony of the State House to the thousands of Bostonians — merchants, artisans, laborers, families — who gathered in the square in front of the building. What a powerful way to learn the news, I thought — together, receiving it directly from one of the revolutionaries, so different from our solitary experience on our phones today.

Around this time the roaring of the Celtics fans grew louder. Through the opening between the buildings, we could see the duck boats filled with Celtics players in the distance. Some people sprinted toward the heart of the celebration. “If you want to see the players, I’ll be right here,” Jules offered. But nobody in our group seemed interested in joining the boisterous crowd, and we moved on.

On our way to the North End, in a neighborhood known as Little Italy, we walked past the historic taverns that served as hubs for disseminating information about the plans of the British. I bought a baguette at a bakery and we shared it as a group as we listened to stories about the secret network of spies and informants that the American patriots developed to monitor the movements of the British, and about Paul Revere’s lantern communication system.

These stories infused the neighborhood with a kind of cinematic quality, but also reminded us that even scrappy efforts can accomplish a grand objective. Seeing where the colonists gathered, ate and walked helped me recognize that history is shaped by regular people who are often obsessively working toward a common goal, and it’s often small, messy and happenstance events that make up a grand historical narrative.

Those regular people also had families — some of them, quite large. Jules told us about Paul Revere’s 16 children and what it must have been like for their father to leave them before the famous “midnight ride” to warn the American militia in Lexington of the approaching British forces.

As we overlooked the industrial landscape across the Charles River, we could spot the USS Constitution , the oldest commissioned warship, and the obelisk of the Bunker Hill monument, which commemorates a pivotal early battle in the American Revolutionary War and the resilience of the American forces against British troops.

There, at our last stop, I thought about how this tour turned out to be not exactly what I had expected — full of detours, revelry and chaos. In some ways, though, my tour seemed an apt symbol of America, with its chaotic and sometimes incongruent blend of old and new, the varied passionate pursuits of the many groups of people who live here, and the “creative rerouting” that America has had to take on its journey through history.

History is not the only way of knowing a place — we all connect with America in different ways based on what we love and what we value. But despite my hangups about history, I found that the stories of the American Revolution found along the Freedom Trail — with the backdrop of the Celtics procession — deepened my sense of home in America and brought Boston to life in a new way. The facts and dates of the American Revolution are still blurry in my head, but what’s clear is that the freedom born in this city is a gift and one that each generation is charged with renewing.