The Freedom Trail: A Walk Through Colonial Boston

Melinda Parks


Hollywood loves to exaggerate and perpetuate the stereotypes associated with Boston – the Boston accent, working-class Irish-Americans, old-money New England families, liberal politics – through dramas like Goodwill Hunting and The Departed. But there is more to Beantown than “pahking the cah.” Amid the stereotyped images of modern Boston, there remain vestiges of the Puritan colony that sprouted up nearly four centuries ago on a tiny peninsula. Following the red brick path marking the Freedom Trail, one can stroll along streets where famous colonial figures walked and explore landmarks that played a crucial role in pre-Revolutionary America.


The geography of Boston has changed dramatically since its foundation in 1630. When John Winthrop and a group of English Puritans settled along the shores of what would become Boston, it was a hilly peninsula containing just 800 acres of land and connected to the mainland by a thin strip known as the Boston Neck. Today, due to landfills and annexation, the city covers about 2,400 acres – three times the size of its colonial settlement. Boston’s topography also evolved as settlers used its hilly terrain to fill in the coastline. To the west of the colony stood three mountains known together as the Trimount, but the city leveled two of these peaks during the 19th century to fill Mill Pond and what is now Charles Street; the middle mountain, called Beacon Hill, was also reduced and smoothed, but still exists today.


Despite the expansion and alteration of Boston’s land, many streets from the original colony still wind through the city as mementos of a time long past. The earliest Bostonians settled along State Street and Washington Street, the colony’s two main thoroughfares. Washington Street also traces the route of the Boston Neck where it once connected the settlement to the mainland. Colonists spread from State and Washington Streets northeast along the shore to form the North End, and southeast to form the South End, now Boston’s financial district. Although the peaks of the Trimount are gone, their namesake lives on in Tremont Street. Along these and other venerable Boston roads stand the colonial buildings made famous by the Freedom Trail.

Starting in the North End, on Hull Street, Copp’s Hill Burying Ground was created in 1659 and exists as the second-oldest cemetery in Boston. Named after the family who settled there around 1635, the hill stood 10 feet higher during colonial times than it does today, having been cut down for use as landfill. For many years, colonists dug graves haphazardly along the field, but the city later organized the headstones into rows, added paths, and opened the cemetery to the public. Many early colonists are buried here, along with notable individuals such as Puritan ministers Increase and Cotton Mather, builder of the USS Constitution Edmund Hart, and Robert Newman, the sexton who may have lit the signal lanterns during Paul Revere’s ride.


If you walk southeast down Hull Street where it intersects with Salem Street, you will see the Old North Church. Built in 1723, it is the oldest church in Boston and the site where two lanterns shone to warn patriots in Charleston of the British troops’ impending approach across the Charles River. Although no definite record tells us who lit the lanterns, historians surmise that it was either a sexton named Robert Newman or a vestry member named Captain John Pulling Jr., as both had access to the church and as both were patriots. Regardless, visitors can view the building as it appeared during colonial times, for it has changed very little over the past 250 years. Inside, you will see white high box pews still bearing plaques with the family names of their original occupants, as well as brass chandeliers installed in 1724 and a clock built in 1726.


Continue south along Salem Street, take a left onto Prince Street, and follow it to North Square, where you will find the oldest building in downtown Boston: Paul Revere’s house. The residence was built in 1680, and Revere purchased it in 1700 and lived there with his growing family until 1800. In 1902, his great-grandson bought the building to protect it from demolition, and within the next few years the Paul Revere Memorial Association formed to preserve and restore it. Most of the original structure remains. Period furniture is arranged inside to resemble a colonial home, to demonstrate how Paul Revere once lived.

If you move south out of the North End headed toward North Street, you will come upon Faneuil Hall, surrounded by the bustling shops and restaurants of Quincy Market. Peter Faneuil, a prominent merchant, used the great fortune he inherited from his uncle in England to construct and donate Faneuil Hall to Boston in 1742. The first level contained a lively marketplace while the second level, nicknamed the “cradle of liberty,” provided a space for town meetings. There, colonists discussed and protested British taxation. The grasshopper weathervane perched atop Faneuil Hall, an imitation of the London Royal Exchange weathervane, was erected in 1742 and is the most recognizable feature of the building.


From Faneuil Hall, take Congress Street going south, turn west onto State Street, and follow it to Washington Street, and you will see a building constructed in 1713, made of brick and having a prominent, white balcony protruding from beneath statues of a lion and a unicorn. This is the Old State House, location of the British government in colonial Boston and of the Massachusetts Assembly, and site of important events leading up to the Revolution. Here, patriot heroes debated Boston’s future. Here, the governor stood upon the balcony and reasoned with a mob following what would come to be known as the Boston Massacre; a circle of cobblestones outside the Old State House serves as a memorial for this “massacre,” which resulted in five deaths. Here, too, the Declaration of Independence was read from the balcony when it arrived from Philadelphia, inspiring Bostonians to burn the lion and unicorn statues, symbols of England’s power (they were later replaced). When the Massachusetts government transferred to the New State House following the Revolution, the Old State House served several purposes before the Bostonian Society restored it in 1881 and transformed it into a museum.


The Old South Meeting House stands just south of The Old State House on Washington Street. The second oldest surviving church and the biggest building in colonial Boston, it was built in 1729 and utilized as a space for large gatherings. The most famous of these occurred when thousands of colonists assembled to discuss the tax imposed on a cargo of tea held by British ships docked at the harbor; in the end, the Sons of Liberty dressed up as Indians and dumped all the tea overboard. In response to the Tea Party, British soldiers took over the Meeting House, ripped out and burned the pews, and transformed it into a military riding school. Yet the Old South Meeting House remains standing due to efforts from the Old South Association, which saved it from demolition in 1875, and which converted it into a museum. The Meeting House tower still retains the clock that was installed in 1770.

Moving northwest on School Street toward the corner of School and Tremont, you will find Boston’s oldest cemetery: King’s Chapel Burying Ground, established in 1630. Notable gravestones at the Burying Ground include John Winthrop, the first governor of Boston, John Wilson and John Cotton, early Boston ministers, William Dawes, Paul Revere’s companion during the famous midnight ride, and Charles Bulfinch, a prominent early American architect. Although the cemetery shares King’s Chapel’s name, it originally had no affiliation with the church. When King James II attempted to consolidate the New England colonies under the governance of Edmund Andros at the end of the 17th century, Andros decided to build an Anglican church in Boston. The Puritan colony, enraged, refused to sell him land for his project, and so he seized a corner of the burying ground and disturbed many graves to build the chapel. Construction was completed in 1754. Today, it retains the original pulpit and sounding board built in 1717.


Farther south along Tremont Street lies the Granary Burying Ground, Boston’s third-oldest cemetery, first used in 1660. Although it is estimated that up to 5,000 bodies lay buried there, only about 2,000 gravestones remain today, as headstones were knocked down or lost when officials reorganized them into straight lines. The Granary Burying ground is the final resting place for many of Boston’s most famous patriots, including Samuel Adams, Paul Revere, Peter Faneuil, and John Hancock, as well as the victims of the Boston Massacre who lie in one mass grave.


Stroll south a short way along Tremont Street, and you cannot miss the 50 acres of open, grassy land constituting America’s oldest public park. In the Common, so called because it was “common” land shared by all colonists, settlers grazed their livestock, trained their militia, and constructed stocks to punish law-breakers. Gallows stood at the location of the current playground, where public hangings occurred in cases of witchcraft, piracy, and heresy.


Spend a day or two meandering down the Freedom Trail and exploring the sites described above. Take a guided tour. Read the informational plaques. Sit in the beautiful old buildings and imagine the people who sat there, the events that took place there. Soak in the history and get a picture of the Boston that’s not shown by Hollywood.


Author Bio:

Melinda Parks is the pen name of a contributing writer at Highbrow Magazine.


Photos: Jeff Gunn; Mikkashar; Boston Public Library; Greater Boston Visitors and Convention Bureau (Flickr - Creative Commons).


For Highbrow Magazine


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