Two Weeks to Travel’s Guide to the Freedom Trail

The Freedom Trail

Freedom Trail Map

Boston is a city steeped in history.

From the migration north of the first settlers at Plymouth Rock, to the Revolutionary and Civil Wars and into the modern day era. Boston holds some amazing stories.

To get the best timeline of Boston history make your first stop the Freedom Trail. Boston’s Freedom Trail was first conceived in the 1950s as a way to boost pedestrian traffic along the historic corridors of the state capital, and was officially established in 1974.

A Little More About the Freedom Trail

Stretching approximately 2.5 miles in length, the trail is marked by a thick red line (usually brick, sometimes painted) that runs through the sidewalks and streets of Boston.

Follow the path to 16 historic sites, which give a snapshot of the history of Massachusetts, and actually some of the history of America itself.

Each site along the Freedom Trail played a vital role in the birth of the United States and is marked with informational plaques for any visitor to have a mini history lesson.

Sites Along the Freedom Trail

Freedom Trail bricks

Freedom Trail path.

There are 16 historic places on the Freedom Trail:

Boston Common
Massachusetts State House
Park Street Church
Granary Burying Ground
King’s Chapel
King’s Chapel Burying Ground
Benjamin Franklin Statue/Site of First Public School in America
Old Corner Bookstore
Old South Meeting House
Old State House
Site of the Boston Massacre
Faneuil Hall
Paul Revere House
Old North Church
Copp’s Hill Burying Ground
Bunker Hill Monument
USS Constitution

Whew, now that’s a list. Lots of stuff to see.

Each of these sites provides information on specific events that occurred in history. Not to mention it’s the perfect way to enjoy the sites and sounds of Boston at your own leisurely pace.

Winding through the diverse areas of Boston, main roads and skinny alleyways, you’ll be able to get a real feeling of the vibrancy of the city.

Alright, I told you this was a guide, so let’s learn a little bit about each stop shall we? Get your thinking caps on, kids!

Boston Common

  • Established in 1634 it’s America’s oldest public park.
  • Colonists first purchased the 44 acres from William Blackstone (the first European settler in Boston paying the equivalent of $0.25 each, the land was used for cattle grazing.
  • Before the American Revolutionary war in the early 1770s the Common was where the British Army set up camp and left from to march to Lexington and Concord in April 1775.
  • Did you know that the western edge of the Common (at Charles Street) used to be waterfront property? The land around it was created from fill during the mid to late 1800s.
  • *Off the beaten path* Head to the corner of Washington and Boylston Streets, on the DMV building you will find a plaque on the Liberty Tree. In the 1760s the Sons of Liberty led by Samuel Adams and Paul Revere would meet under a huge elm tree to protest against British rule. The British chopped the tree down in 1775 as an act of punishment for defiance.

Massachusetts State House

  • Charles Bullfinch was the architect that designed the building which was finished in 1798.
  • The actual land that the State House sits on was once John Hancock’s (the guy with the fancy signature on the Declaration of Independence) cow pasture.
  • The actual dome that is one of the distinguishing features of the State House was actually made of wood and then covered in copper by Paul Revere.
  • *Fun fact* The dome is now covered in 23 karat gold but during World War 2 it was actually painted black because Government was afraid that if the Axis Powers ever made it to the East Coast it would be seen as a target.
  • *Off the beaten path* Head across the street to the Robert Gould Shaw memorial (remember the movie Glory?) and from there pick up the Black Heritage Trail to sites like the African Meeting House and stops on the Underground Railroad.

Park Street Church

  • The church was first built in 1809 with direction from the Reverend Abile Holmes, the patriarch of a pretty famous family. His son was the famous author Oliver Wendell Holmes, and his grandson was US Supreme Court Justice Oliver Wendell Holmes Jr.
  • At the time, the steeple (a whopping 217 feet) was the tallest building in Boston, and the first landmark that could be seen from Boston Harbor.
  • Members of this church were active and outspoken proponents of freedom for many groups, women and salves, especially.
  • *Fun fact* The original building that was built on the same spot in the 1700s was where the sails of the USS Constitution were sewn.
Sign to Granary Burying Ground

Sign to Granary Burying Ground

Granary Burying Ground

  • This cemetery was opened all the way back in 1660 to make space after the cemetery across the street became too overcrowded, however now, there are actually over 5,000 bodies buried here.
  • Some call Granary Burial Ground the “Westminster Abbey” of Boston because there are so many famous people buried here such as the family of Ben Franklin, Sam Adams, John Hancock and Paul Revere.
  • *Fun fact* See if you can find the grave for Anne Pollard, who when she arrived as a young girl in 1630 was the first non-Native American woman to set foot in Boston. Incredibly, she lived to age 105.
  • *Sort of fun fact* A few years ago a visitor actually fell into a previously hidden and undiscovered tomb just yards from Paul Reveres grave. Thankfully, she was just fine afterwards.

Kings Chapel

  • The first church built here was originally wooden, and actually reclaimed public land because at the time no Puritan would sell their land for an Anglican Church to be built upon. So the King of England allowed the Royally appointed Governor to take the land.
  • In 1749 the stone church you see today was built, it was actually constructed around the old wooden structure, and as the stone walls went up, the wooden ones were dismantled and tossed out the door and windows.
  • Inside the church you’ll see that the pews are set up as boxes, each family paid rent to keep their boxes private ad decorate them as they wish. Check out box 33 to see Paul Revere’s family pew.
  • *Fun fact* When the British ended their siege of Boston in 1776, the loyalist members of the church escaped to Canada…with the Kings silver communion pieces, oops.
Kings Chapel Burying Ground

Kings Chapel Burying Ground

Kings Chapel Burying Ground

  • This burying ground was actually the first in all of Boston.
  • You’ll find a few famous residents in here too, including: John Winthrop (the first Governor of Massachusetts Bay), and former Governors William Shirley, John Leverette and John Davenport.
  • Many of the tombstones have some incredibly intricate carvings on them, explore around and you will see things like skulls with wings (symbolizing death and rising to heaven) as well as an old man with a sickle, bones and flowers.
  • *Fun fact* Look for the grave of Elizabeth Pain, she was rumored to have been the inspiration for Hester Pryne in The Scarlet Letter (aka Demi Moore in the movie) because the stone contains an engraved heraldic letter, something that was very unusual for the time.

Benjamin Franklin Statue

  • At this spot you’ll find a statue of Ben Franklin. You might think of him being associated with Philadelphia, but he was actually born and raised in Boston.
  • The statue was actually the first erected in Boston in 1856, and was also the first statue of a person in Boston. The building behind it is the Old City Hall, used from 1865-1969.
  • Also at this site is the original site of Boston Latin School, the first and oldest public school in America. The school is still in operation today, though at a new location, and is considered one of the best in the country.
  • *Fun fact* In the same courtyard where you will find the Franklin statue is a small bronzed donkey, representing the Democratic party in Massachusetts. The two bronzed footprints along side it urge “to stand in opposition.”

Old Corner Bookstore

  • Looks like a pretty normal building right, well it was actually built in 1712, talk about solid construction!
  • In the early 1800s the building was bought and turned into a small publishing company which published the books of some of America’s most famous authors at the time (even now): Harriet Beecher Stowe, Henry David Thoreau, Ralph Waldo Emerson and Henry Wadsworth Longfellow.
  • The bookstore became well known as a meeting place for authors and intellectuals to meet and discuss politics and events of the day.
  • *Fun fact* Originally on this spot was the home of Anne Hutchinson, which burned down in the early 1700s. She was exiled from Massachusetts for life for heresy against the Bible. Later she was credited with being one of the biggest proponents of religious freedom in the US.

Old South Meeting House

  • The Old South Meeting House was actually first built as a Puritan Church, it doesn’t look like a ‘typical church’ because the Puritans, who fled England for religious reasons wanted their places of worship to be more like a meeting place and less like a church.
  • This meeting house was home to a lot of revolutionary spirit during the early 1770s, it was here that up to 7,000 people would attend meetings where people like Sam Adams would speak against the British Rule.
  • In it’s time, this was the largest building in all of Boston.
  • *Fun fact* By 1775 the British were pretty sick of the defiance of many of Boston’s residents. To punish them, they tore down the inside of the Meeting House, filled it with dirt, and used it as an indoor riding arena for the generals horses.
Old State House

Old State House

Old State House

  • The building has stood on this land from 1658, first as a wooden structure, then the replacement you see here from the early 1700s. It was the seat of power of the British Crown before the Revolution and served as the capital building of the Commonwealth afterwards.
  • For many of the citizens of Boston who were against the British rule, this building was viewed as the negative symbol of British power. All declarations, laws and rules that the Crown installed over the citizens were read to them from the balcony (Queen Elizabeth II also read from this balcony during her tour of America at the Bicentennial in 1976).
  • In acts of defiance members of the Sons of Liberty as well as others who wanted sovereignty would stand in front of the building and give speeches against the British.
  • *Fun fact* You’ll notice on the East face of the building the lion and unicorn (symbols of the British crown) these are replacements from the 1880s because the originals were taken down and burned on the street after the reading of the Declaration of Independence.

Boston Massacre Site

  • Just outside the Old State House, you’ll find a circle of cobblestones in the street, this is the site of the Boston Massacre.
  • As you’ve probably guessed by now, tensions between many of the residents of Massachusetts and the British personnel in Boston was rising really qickly from the 1760s on. It was on the day of the massacre, March 5th 1770 that everything escalated.
  • According to historical sources, an argument erupted between a growing crowd and a small group of British soldiers, things escalated and when one of the soldiers was hit with a flying object from the crowd he fired, causing the rest of the soldiers to shoot as well. Once the dust settled, five colonists lay dead. Uh oh.
  • Word of the massacre spread throughout the rest of the colonies, with the help from a coordinated propaganda campaign from the Sons of Liberty, which many historians cite as the first domino falling towards revolution.

Faneuil Hall

  • These series of buildings were built for dual purpose back in 1742, with the basement floors as a commercial marketplace area and the upper floors used as meeting houses. Even after all this time, the usage now is pretty much the same.
  • Many historians refer to this place as the ‘cradle of liberty,’ as many people met here to rally against taxation without representation, it was also here that the first ideas of having a Continental Congress were discussed in secret.
  • *Fun fact* Head up to the 4th floor of the main visitor building and view the museum on the Ancient and Honorable Artillery Company of Massachusetts, founded in 1638, it’s oldest in the Western Hemisphere, and 3rd oldest in the world.
  • *Fun fact* Look up and you’ll see the giant golden grasshopper on top of the marketplace building from 1742. In 1974 the 80 pound grasshopper was stolen and held for ransom, but eventually recovered by the Boston Police.
  • *Off the beaten path* Adjacent to Faneuil hall on Union Street is the New England Holocaust Memorial, consisting of six tall glass towers in a row with numbers etched on them, it makes a powerful statement.
Freedom Trail Marker

Freedom Trail Marker

Paul Revere House

  • Paul Revere was one of the most famous patriots during the American Revolution. A silversmith by trade, he was the focus of the famous poem by Henry Wadsworth Longfellow, the Midnight Ride of Paul Revere.
  • This house is actually the oldest still in existence in Boston. Paul Revere bought the wooden structure in 1680 and incredibly, at that time the home was 100 years old!
  • It was from this house that Paul Revere left from on his famous ride with William Dawes to alert Lexington and Concord that the British were on the move. Ironically, the neighborhood he lived in was very pro-British at the time.
  • *Fun fact* Paul Revere was married twice, his first wife died during childbirth. Between his two wives he had 16 kids. Most of his kids, along with his wife and mother all lived in this house at the same time.

Old North Church

  • This stone church is the oldest in Boston built as its original structure in 1723.
  • The church is most famous for being the place were lanterns “one if by land, two if by sea” were hung to alert riders Paul Revere and William Dawes that the British troops were on the move and to alert the suburban militias.
  • The bells used in the church were cast in 1744 in England and brought across the Atlantic to America, and contains the inscription: “We are the first ring of bells cast for the British Empire in North America, A.R. 1744.”
  • *Fun fact* In 1757 a man named John Childs made a glider out of feathers, and jumped from the top of the old north church flying approximately 700 feet before reaching the ground, successfully marking the first ‘flight’ in america.

Copp’s Hill Burying Ground

  • Getting tired of graves yet? Don’t worry, this is the last one.
  • Some famous inhabitants are Increase and Cotton Mather (involved in the Salem witch trial hysteria), Robert Newman (who placed the lanterns in the Old North Church), and Edmund Hartt (builder of the USS Constition).
  • Also in this graveyard are the unmarked graves of over 1,000 African Americans, both freed and slaves who lived in the ‘New Guinea’ section of Boston.
  • *Fun fact* Some of the headstones were used as target practice by British troops during occupation. A favorite target was Daniel Marcoms headstone which reads “A true Son of Liberty, a friend to the publick, an enemy to oppression, and one of the foremost in opposing the Revenue Acts on America.”
  • *Off the beaten path* Leaving the cemetery instead of following the red line go right down Snow Hill Street which merges with Charter Street until you hit Commercial Street walk to Puopolo Park and there you will find a small sign commemorating the great Boston Molasses Flood. In 1919 a molasses tank exploded causing a 40 foot wave of molasses traveling at 35 mph. 21 people and a dozen horses died, and hundreds more were injured. Local lore is on a hot summer day you can take a deep breath and still smell the molasses.
The Bunker Hill Monument.

The Bunker Hill Monument.

Bunker Hill Monument

  • Now we start heading over to Charlestown (where my family is from originally).
  • The Bunker Hill Monument commemorates the Battle of Bunker Hill on June 17th 1775, even though it actually took place on nearby Breed’s Hill.
  • The Americans lost this battle, but it proved to be a turning point in the revolution, the colonists were outnumbered almost 2-1 against the British Army only surrendering the hill because they had run out of munitions. It was after this battle that the Americans believed they could stand toe to toe with the British.
  • *Fun fact* In front of the monument is a statue of Colonel William Prescott who famously told the colonial farmers not to ‘fire until you see the whites of their eyes’ in order to save ammunition during the battle.
  • *Fun fact* At one time the monument was fitted with a light and used as a beacon of sorts for incoming ships to navigate through Boston Harbor.

USS Constitution

  • Alright kids, we’re at the end of the line now. See that big boat in front of you, it’s the USS Constitution, built in 1797 it is the oldest ship in the US Navy and the oldest commissioned warship afloat in the world. George Washington himself ordered it to be built.
  • She got her nickname ‘Old Ironsides’ during the war of 1812 when at battle it seemed that the cannonballs that were fired at her just bounced off her sides. This caused people to think the boat was actually made of iron not wood.
  • The USS Constitution is technically considered to be a museum ship. But it’s manned by about 65 crew members, all of whom are active duty in the US Navy. A duty assignment to the Constitution is considered to be a special honor.
  • *Fun fact* The ship still sails! Each year on the 4th of July the Constitution is taken out of Boston Harbor and turned around, so her sides weather evenly. People apply to be in a lottery in order to be able to enjoy the ride.

Well there you have it, a quick and dirty guide to the Freedom Trail for you. Next time you’re in Boston make a few stops along the trail and let me know what your favorite spots were!

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