Last spring, my niece Hannah and her husband Adam moved to Boston. They knew nothing about Beantown, so I offered to show them around. I fancied myself an expert on the city, having worked there during a couple of off terms while I was a student at Dartmouth College back in the 1980s. Since then, I’ve visited the city many times for various occasions, and I constantly travel through it en route to my adventures around the globe. Deciding what to see in such a large, multifaceted city was the question. All three of us loved hiking in mountains, which easily translated to walking in cities. With that realization, trekking the Freedom Trail was the perfect choice. We could get some exercise; see downtown Boston, the North End, and Charlestown; and explore some of the city’s most famous landmarks.

I had walked the Freedom Trail many times, at least sections of it. It’s impossible to have lunch at Faneuil Hall, one of my regular lunch spots in the city, without taking at least a few steps along the red brick line that marks the trail. When strolling around Boston Common or walking down Tremont Street, the red line had often been underfoot, but when the day approached to show Hannah and Adam around, I realized it had been about 15 years since I had walked the 2.5-mile-long urban path in its entirety. It would be an education for all of us.

The Freedom Trail is part of the National Park system. Though there is no official start and finish to it—you can pick up the trail at any of its 16 official landmarks or at any point along the red line embedded in the sidewalk and that winds its way through the city—the usual starting point is at the Boston Common Visitor Center. We found a parking spot on nearby Beacon Hill, then made our way to the Common to begin our trek. To our delight, a man dressed like General Lafayette greeted us outside the building. After that, modern and colonial Boston began to blur as the people and events that led up to and during the American Revolution came into focus, starting with Boston Common.

Downtown Boston

Though people often refer to Boston Common as Boston’s Central Park, this 44-acre green space in the heart of the city is older, established in 1634 versus 1858. It’s the oldest public park in the United States. Puritan colonists purchased the land from the first European settler in the area, an Anglican minister named William Blackstone, as a place to graze their cows and hang criminals and heretics. During the British occupation of Boston in 1775, a thousand British troops camped on the Common.

From the visitor center, we followed the red brick ribbon uphill toward the Massachusetts State House with its showy gold dome. Both the legislative and executive branches of the Massachusetts government are in this national historic landmark. Though the state house is old, dating back to 1798, it’s the “new” state house. The original one, built in 1713, was farther along the Freedom Trail. Two famous Bostonians who figured prominently in the American Revolution—John Hancock and Paul Revere—were connected to the state house in interesting ways. It was built on Hancock’s cow pasture and Revere first coated the dome with gold, actually gold-copper.

From the Massachusetts State House, we followed the trail down Tremont Street to Park Street Church and the adjacent the Granary Burying Ground. The cemetery gate was open, so we wandered in. Named for a 12,000-bushel grain-storage building that used to stand beside it, the Granary Burying Ground is the third oldest in the city, dating back to 1660. Among the 2,300 graves, we found some influential folks, including US President Samuel Adams, John Hancock,
and Robert Treat Paine, all of whom signed the Declaration of Independence,
and Paul Revere.

A prominent memorial in the middle of the burial ground said “Franklin” in bold letters. “I wonder if that’s where Benjamin Franklin was buried?” asked Hannah. “He was from Boston.”

“Nope. It says Josiah and Abiah,” replied Adam. In fact, those were Franklin’s parents, though we came across the man two stops farther along the trail at the Boston Latin School.

After passing a second burial ground by King’s Chapel—Boston’s oldest, where John Winthrop, the first governor of Massachusetts, and Mary Chilton, the first person to step ashore from the Mayflower, were laid to rest—we came to a statue of Benjamin Franklin, which marked the spot where the Boston Latin School once stood. Founded in 1635, Boston Latin School is the oldest public school in America. At first, it offered free education only to boys. Five of the signers of the Declaration of Independence—Franklin, Adams, Hancock, Treat Paine, and William Hooper—attended. Though the original schoolhouse was torn down in 1745, the school still exists, now in the Fenway neighborhood, and is open to both boys and girls. We all giggled upon learning that Franklin, the brilliant statesman and inventor, dropped out before graduating!

Our next stop, the Old Corner Bookstore, is the oldest business in Boston. During the 1800s, the building housed the prominent 19th century bookmaker Ticknor and Fields, which published such classics as Thoreau’s Walden, Hawthorne’s The Scarlet Letter, and Longfellow’s Midnight Ride of Paul Revere.

From there, we passed the Old South Meeting House. Originally a Puritan house of prayer, Benjamin Franklin was baptized here. Its members included James Otis and William Dawes, two other riders with Paul Revere who warned that the British were coming. The meeting house is perhaps most famous as the place where 5,000 people gathered just before the Boston Tea Party. To the crowd, Samuel Adams said, “This meeting can do nothing more to save the country,” which was the signal to dump the tea into the harbor.

The Old State House and the large, round marker—the site of the Boston Massacre in front of the state house—were next. During the winter of 1770, tensions peaked due to the British occupation and heavy taxes on daily essentials. A mob of about 300 locals surrounded a group of soldiers at this spot and started harassing them with snowballs, rocks, and other objects. The soldiers fired into the crowd, killing five and wounding six civilians. Though skyscrapers surrounded and dwarfed this historic site, they hardly overwhelmed it. Standing on the place that escalated the desire for independence among all 13 colonies, we could only gaze at one of freedom’s hallowed spots, imagining the tension of that time period in American history.

A little farther, we wandered through Faneuil Hall, which is often called the “home of free speech” and the “cradle of liberty” because it became an important meeting place leading up to the American Revolution. Starting in 1764, people gathered here to protest the Sugar Act, the Stamp Act, and later the Tea Act, the Townshend Duties (surcharges on lead, glass, paper, paint, and tea) and the British occupation. We paused to watch an escape artist free himself from a straightjacket, an unwitting metaphor for the colonists freeing themselves from the suppressive rule of the British crown.

Then we enjoyed a lobster roll and clam chowder before continuing our walk. “You can’t stroll through Quincy Market without eating something,” I crooned, delighting in every bite. As we perched on the edge of a low wall munching on lunch, the weathervane atop Faneuil Hall caught Hannah’s eye. “That’s an odd weathervane,” she observed. “It looks like a cockroach.”

“It’s a golden grasshopper,” I corrected, remembering a historical tidbit that I learned on my first visit to Boston: “During the War of 1812, if
someone asked you what’s on top of Faneuil Hall and you didn’t know,
they assumed you were a spy.”

The North End and Charlestown

From Faneuil Hall, we wound our way through the North End past Paul Revere’s home, the only site on the Freedom Trail that’s a home. From there, the path led to the Old North Church, the oldest standing church in the city and the starting point of Revere’s famous ride. When Paul Revere learned that the British were rowing across the Charles River rather than approaching by land, he ordered two lanterns hung in the church steeple, “two if by sea,” to signal the Americans.

The man who hung the lanterns, Robert Newman, was buried at the next stop, Copp’s Hill Burying Ground. About 12,000 colonists were laid to rest here, though there are only 1,200 markers. The British positioned their
cannons here during the Battle of Bunker Hill due to its strategic position, overlooking the colonial wharves, and used the tombstones for target practice. Builders sometimes snitched the tombstones for foundations, and old plots were often resold. This cemetery is now a regular stop on ghost tours of Boston, apparently haunted because of such
disrespect for the dead.

From there, we continued through Charlestown to the Bunker Hill Monument, which looked like a miniature Washington Monument atop a modest rise of land. The Bunker Hill Monument commemorates the Battle of Bunker Hill in 1775, which the Americans lost. What’s more, it’s on Breed’s Hill, not on Bunker Hill, which is nearby and taller. Breed’s Hill was where the heaviest fighting occurred because that’s where the Americans were positioned after accidentally fortifying the wrong hill in the dark.

Our last stop on the Freedom Trail was the Charlestown Naval Yard, where the USS Constitution, the oldest commissioned warship in the US Navy still in service, is moored. Launched in Boston in 1797, she fought in the War of 1812, defeating five British ships
singlehandedly. She earned the nickname “Old Ironsides” because cannonballs seemed to bounce off her sturdy wooden sides as if they were made of iron. Interestingly, the iron fastenings on the boat were made by Paul Revere.

Our trek over, I asked Hannah and Adam how they liked the Freedom Trail. “I learned a lot,” said Hannah. “The United States wouldn’t exist today without Bostonians like Paul Revere, Samuel Adams, and John Hancock.”

“I’m not much of a history buff, but I sure gained an appreciation for the people and events that contributed so importantly to the freedom we enjoy today,” added Adam. And it was a great introduction to the city, too!