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CityPASS Home  »  City Traveler Blog  »  Love History? Boston’s Freedom Trail Takes You Back in Time

City Traveler Blog

Love History? Boston’s Freedom Trail Takes You Back in Time

Not many folks realize this, but there are actually two Bostons.

The first Boston is the one that most people are familiar with: the city known for its distinctive skyline, defined by the easily-recognizable Prudential Center and John Hancock Building. It’s the Boston that’s a sports mecca (Red Sox and Bruins), the home of first-rate colleges and universities (Harvard, Boston University and Northeastern), a world-class center of performing arts (the Theater District, Symphony Hall, and the Boston Opera House), and a shopaholic’s paradise (Copley Square, Newbury Street).

The second Boston is very different, but just as alive and vibrant. It’s the city linked together by the Freedom Trail, a red brick walking path that leads you through the oldest parts of the city. The 2.5 mile walk begins at the Boston Common and ends at the USS Constitution; along the way, it takes you back in time to the Colonial era, enabling you to encounter some of the most important sites in our nation’s history.

There are 17 official sites on the trail, as well as numerous “off trail” locations and significant locations marked by plaques or ground markers. You can walk the trail on your own, using a Freedom Trail map as a guide. But to get the real experience of stepping through time, sign up to follow the trail with one of the Freedom Trail Players, historic characters who were at the front line of the revolt against Britain. As one of these “real” citizens from the colonial era, or one of its notable historical figures (such as Abigail Adams, Crispus Attucks, and Paul Revere) lead you on a tour of the Trail, you’ll see history – the birth of our nation -- through the eyes of those who lived it.

Here’s an overview of the seventeen sites of the Trail. Note that the Freedom Trail offers different versions of its guided tours, which feature some, but not necessarily all, of these sites. You'll quickly see why the Freedom Trail is one of the most popular things to do in Boston.

Boston Common

Many of the Freedom Trail tours begin at the Visitor Information Center (139 Tremont St.) on Boston Common. The Common makes a great stepping-off point into Boston’s history; in 1634 (long before the swan boats graced its pond), it was collectively purchased as by the Puritans as a “common,” or shared land to graze their sheep on, making it the oldest public park in our country. It’s played a number of other roles in Boston’s history, including being a site for public punishments such as whippings and hangings, a training field for soldiers, and a place for public celebrations.

Massachusetts State House

Across the street from Boston Common is the Massachusetts State House, a majestic structure featuring a golden dome set upon 6.7 acres of land, built in 1798. Considered the “new” State House (as opposed to the Old State House, which you’ll visit later on the Trail), it is still today the place where Massachusetts’ legislators meet to run the affairs of the state.

Park Street Church

Founded in 1809 by Congregational ministers, Park Street Church became the one of the first centers of Boston’s Abolitionist movement, hosting passionate anti-slavery lectures and speeches. Other causes, such as prison reform and women’s suffrage, were also supported here.

Granary Burying Ground

Next to the Park Street Church is the Granary Burying Ground, the final resting place of many of Boston’s most famous patriots: John Hancock, Sam Adams, James Otis, the parents of Benjamin Franklin, and some of the victims of the Boston Massacre, including Crispus Attucks, Samuel Gray, Samuel Maverick, James Caldwell, and Patrick Carr.

King's Chapel

The King’s Chapel was originally a small non-Puritan church, built in 1688 and used by the King’s men, who occupied Boston to enforce British law. As the congregation outgrew the tiny church, architect Peter Harrison designed Georgian-style a stone structure around the original wooden church, which was then disassembled and removed through the windows of the new construction. It’s worth taking the time to step inside and look around; the church’s interior is magnificently appointed.

King's Chapel Burying Ground

Next to King’s Chapel is its cemetery, the first (and therefore oldest) burying ground of Boston, founded in 1630. Many notables are buried here, including Mary Chilton, the first woman to step off the Mayflower; John Cotton, the (in)famous Puritan preacher; Elizabeth Pain, whose headstone may have inspired Hester Prynne's in The Scarlet Letter; and John Winthrop, the first Governor of Massachusetts.

Benjamin Franklin statue and the former site of Boston Latin School

America’s oldest public school, Boston Latin School, was first situated on School Street; today, a statue of one of its students, Benjamin Franklin, marks its original location.

Old Corner Bookstore

Lovers of early American literature are sure to be thrilled by this stop. Originally built as an apothecary shop in the early 1700s, the Old Corner Bookstore opened in 1828. Under publishers Ticknor and Fields, who ran it from 1833 to 1864, the bookstore and printing shop became the nation’s leading publisher, producing the works of Henry Wadsworth Longfellow, Harriet Beecher Stowe, Nathaniel Hawthorne, Ralph Waldo Emerson, John Greenleaf Whittier, Oliver Wendell Holmes Sr., Charles Dickens and Louisa May Alcott.

Old South Meeting House

Across the street, you’ll find one of the most famous sites from colonial history -- the Old South Meeting House. On December 16, 1773, 5,000 people met in the Meeting House to debate British taxation, and after the meeting the Sons of Liberty raided a nearby tea ship, dumping its cargo into the river. The incident became known as the Boston Tea Party and was one of the seminal events leading up to the American Revolution.

Old State House

Built in 1713, the Old State House building (a CityPASS attraction) housed the Massachusetts legislature and is the oldest surviving public building in Boston. Its real claim to fame, however, is that it was the epicenter of the activity leading up to the colonists’ fight for independence. Patriots Samuel Adams, John Adams, and John Hancock led many spirited debates on how to respond to England’s oppression of the colonists. The Boston Massacre took place right outside the building. And from its balcony in 1776, one of the Sons of Liberty proclaimed the Declaration of Independence to the citizens of Boston for the first time.

Site of the Boston Massacre

A ring of cobblestones outside of the Old State House marks the site of the Boston Massacre, one of the most important events leading up to the War for Independence. On March 5th, 1770, a British soldier, Private Hugh White, got into a confrontation with a young apprentice named Edward Garrick over Garrick’s insult of his commanding officer. Private White struck Garrick with the butt of his musket, and subsequently a mob formed, hurling insults and snowballs at White and the redcoats who’d arrived to back him up. A shot was fired into the crowd, then more, and when the smoke cleared, five colonists were dead or dying. The Boston Massacre became a defining moment in the series of events leading up to the colonists’ decision to declare their independence from Britain.

Faneuil Hall

Around the corner from the Old State House is another one of Boston’s most well-known historic sites, Faneuil Hall. While the adjoining marketplace is a major shopping destination, the building itself holds a special place in American history. The idea of “no taxation without representation” began within its walls as colonists argued against the Sugar Act and the Stamp Act. From Faneuil Hall, Samuel Adams (whose statue resides outside the building) led gatherings that would galvanize the colonists into breaking away from England.

Paul Revere House

Contrary to popular legend, Paul Revere didn’t shout “The British are coming!” to warn colonists on the night of his famous ride on April 18th, 1775; eyewitness accounts tell us he warned, “The Regulars are coming out!” Regardless, Paul Revere's house (dating back to 1680, making it the downtown Boston’s oldest building) is where the patriot lived with his wife, children and mother, and it’s the place from where Revere’s famous midnight ride to Lexington began.

Old North Church

On the night of April 18th, 1775, two lanterns shone, just for a few moments, from the 191-foot steeple of the Old North Church. This was the signal that Paul Revere had been waiting for, immortalized years later by the poet Henry Wadsworth Longfellow: “One if by land, two if by sea.” The redcoats were advancing by boat, crossing the Charles River to seize the patriots’ munitions and arrest John Hancock and Sam Adams. From that signal, Paul Revere began his ride into history.

Copp's Hill Burying Ground

Down the street from the Old North Church is Copp’s Hill Burying Ground (established 1659), a cemetery for the North’s End’s colonial residents, including many African-American colonists. It’s notable for several well-known people, including Puritan ministers Cotton Mather and his father Increase Mather (of Salem witch trial fame), and the sexton, Robert Newman, who is reputed to have been the person to hang the two lanterns in the Old North Church on the night of Paul Revere’s ride. It’s also the place where British soldiers stationed themselves to aim their cannons at Charlestown during the Battle of Bunker Hill.

Bunker Hill Monument

The Freedom Trail crosses over the Charlestown Bridge into Charlestown, leading you up to the site of the first major battle of the Revolutionary War – Breed’s Hill (which, through a map mistake, would go down in history as Bunker Hill). It was here that the colonists fended off a force of 3,000 British soldiers, and when they finally relinquished the battle, the ragtag and poorly fortified rebels had produced about 1000 redcoat casualties, demonstrating that they were a force to be reckoned with. The 221-foot granite obelisk that commemorates the battle, built between 1825 and 1842, was renovated in 2007 to allow for better lighting inside and handicapped access. Across the street, The Battle of Bunker Hill Museum contains artifacts from the battle, including a cannonball, a snare drum, and other relics.

USS Constitution

The final stop of the Freedom Trail is the USS Constitution, affectionately nicknamed “Old Ironsides,” the oldest commissioned warship afloat in the world. Although launched in 1797, the 44-gun frigate became famous during the War of 1812 when she defeated five British warships: HMS Guerriere, Java, Pictou, Cyane and Levant. Permanently berthed in the Charlestown Navy Yard, the USS Constitution is open as a museum.

For more information, or to book a tour, visit

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