When I moved from Upstate New York to Boston after college I brought with me my passion for history. What follows is my personal historic walking tour of Boston, which I have given to friends and family who visit from out of town. This post has nothing to do with tech, so if expected to talk technology, you might want to check out my Boston Nerd Tour instead. This tour will mostly follow the iconic Boston Freedom Trail, but will deviate from it from time to time to highlight some of my favorite sites. Let’s get started.
Note: I included a Google Map at the end of the blog to make it easier to follow along.
Bunker Hill from Route 93
In 1775 Charlestown was located on the southern side of a peninsula that was connected to the mainland by a narrow isthmus. There were two hills on the peninsula: Breed’s Hill to the south (toward Boston), and Bunker Hill to the north. While smaller today than they were in Colonial times, those two hills can still be seen by looking to the left from the Zakim. You will have to imagine the water surrounding the peninsula since that was filled in long ago. The high land on which the Bunker Hill Monument resides is actually on Breed’s Hill, and the one further back near where the narrow isthmus connected to the mainland is Bunker Hill. Yes the irony is not lost on anyone that the Battle of Bunker Hill was fought on Breed’s Hill.
Since Breed’s Hill was further south on the peninsula, the Colonists took a risk that the British would not sail around and cut them off from behind. The safer choice would have to occupy Bunker Hill, which being further north on the peninsula, would have been easier for the Colonists to retreat across to the mainland if the British tried to land troops behind them. History has never been clear on who made the mistake of occupying the lower and less defensible Breed’s Hill. But in the end it didn’t matter much since the British leaders discarded their geographic advantage to make a frontal assault on Breed’s Hill. We’ll talk more about the battle later in our tour, but in the words of British General Henry Clinton: “A few more such victories would have shortly put an end to the British dominion in America.”
Park in Boston Common Garage
This is not really a historical stop but you’ll need a place to park. You can find a less expensive place, but you won’t find a more convenient one. Once parked take the elevator up to the Common and we can continue our tour.
George Washington Statue
Prior to the French and Indian War, the Thirteen Colonies were comprised of loyal British subjects that had little to complain about. They had most of the benefits of Englishmen and all the freedoms that came with being a Colonist in the New World. But to pay for the high cost of the French and Indian War, the British Parliament passed a series of taxes on the Colonies starting with the Stamp Act of 1765. This gave rise to increasing resentment among the Colonists, who viewed their lack of seats in Parliament as “taxation without representation.” The protests steadily escalated, resulting in the British sending soldiers to occupy Boston in 1768. The tensions came to a boil in 1770 with the Boston Massacre, in 1773 with the Boston Tea Party, in 1775 with the Battles of Lexington and Concord, and then two months later with the Battle of Bunker Hill.
It was a month after the Battle of Bunker Hill that the Continental Congress sent George Washington to us. With the British isolated in Boston, Colonial militias had gathered from as far away as Virginia to lay siege to the city. Washington was given the job of forming these ragtag volunteers and militias into an army. He improved the defenses, harassed the British, but refrained from making a direct attack on the British soldiers in Boston. When one of Washington’s officers, Henry Knox, returned from Fort Ticonderoga with 60 tons of heavy artillery, Washington seized the opportunity and dug his cannons in to Dorchester Heights, where they were in direct range of the British ships. When the British realized they couldn’t repel the Americans from the heights, they evacuated 11,000 soldiers and Loyalists from Boston, in an event that is still celebrated today as a holiday called Evacuation Day.
The statue you are looking at is what George Washington would have looked when he lived in and around Boston (scaled down of course). Many Americans forget that when Washington commanded troops in Boston, he was in his early 40s and was tall, strong and in the prime of his life. He also was known to be one of the best horse riders of his day. The image by which most Americans know Washington unfortunately is the one on the dollar bill, which was painted later in the General’s life by the local painter Gilbert Stuart. One of the few remaining copies Stuart made of that painting can be found in the Boston Museum of Fine Arts.
The Great Elm
Boston was founded in 1630 by Puritans from the Massachusetts Bay Colony. The Puritans were a movement in the Church of England that believed the church did not go far enough to separate its practices from Catholicism. They believed in moral purity, enacted strong punishments on those that violated their beliefs, and were intolerant to other religious views. I’m sure they had some good traits too, but I suspect there weren’t a lot of people waving goodbye at the docks as John Winthrop and his band of Puritans set sail for the New World.
Most people don’t realize that the land on which Boston resides was the third choice for the Puritans. They first landed north in what is today Lynn, and then briefly considered Charlestown before settling in Boston. When the Puritans first landed on the Shawmut Peninsula, it was comprised of five hills and inhabited by Native Americans. Where you stand now in The Common would have been an open area on the high point of a hill, occupied even then by The Great Elm. This tree became a site of public executions for the Puritans, and was the location of the infamous hanging of the Quaker Mary Dyer, who was put to death for nothing more than practicing her religion. Her death would bring about the beginning of the end of the Puritan theocracy in Boston, and started the transition Boston into a more modern secular city.
Universal Hub CEO and founder, Adam Gaffin, added this story: an Anglican priest by the name of William Blaxton had arrived on the Shawmut Peninsula before the Puritans, and was living among the Native Americans when the Puritans first arrived in Charlestown. It was Blaxton (a.k.a. Blackstone) who invited them over to the Shawmut Peninsula after hearing of their struggles to obtain fresh water in Charlestown. But over time he tired of Puritan intolerance, and was said to have rode out of Boston on a white bull, not stopping until he arrived in Rhode Island (the Blackstone River is named for him). This just adds more evidence to my theory that no one actually liked the Puritans.
The Boston Common Visitor Center
Today the Common is bordered by Beacon Street to the north and by Tremont Street to the southeast. The street name Tremont comes from “Trimountaine”, a reference to the three peaks that once stood here. All that is left today of these hills are Beacon Hill.
The Hancock Manor
The Massachusetts State House
There are scheduled tours of the State House during the week, but unfortunately they are not available on weekends. I had the good fortune last year of being invited by a colleague to go to lunch with Governor Baker. We had lunch in a wing that had been restored to period in the 19th century. The Governor’s wife was kind enough to give us a personal tour, and I had a chance to see some of the historical artifacts and art. If you get a chance to tour the State House, don’t pass it up.
Robert Gould Shaw Memorial
The two gangly trees to either side of the monument are the oldest elm trees in the northeast United States. They were planted by John Hancock himself, who received permission to plant in the public space across the street from his house. These trees are estimated to be about 240 years old.
Park Street Church
Granary Burial Grounds
If you are here on a weekend you will usually find someone handing out maps at the entrance, for which they hope you will tip them on the way out. It’s worth picking up a map or pulling one up on your smartphone as you walk around. Notable graves to visit include Paul Revere, three signers of the Declaration of Independence (Sam Adams, John Hancock, Robert Treat Paine), and the five victims from the Boston Massacre. You should also make a stop by the gravestone for the parents of Ben Franklin. While Franklin is always associated with his adopted hometown of Philadelphia, he was born and raised in Boston.
If you walk a little further down Tremont Street you will find the entrance to the King’s Chapel Burying Ground, which was the first cemetery in Boston. It’s worth a visit since you will find the graves of John Winthrop, the first governor of Massachusetts, and Mary Chilton, the first woman to step off the Mayflower (the Plymouth colony was founded 10 years earlier than Boston just 40 miles to the south).
Benjamin Franklin Statue
Let’s talk for a moment about the statue you are looking at. Most people forget that one of America’s greatest founders, Benjamin Franklin, was born and raised in Boston. As one of 17 children, Benjamin dropped out of Boston Latin School at age 10, and by 12 had been apprenticed to his older brother James. James was a printer, who beat Benjamin and forced him to work long hours. Fed up with the mistreatment, Benjamin Franklin became a fugitive at age 17, leaving his apprenticeship to run away to Philadelphia. But for all his faults, James did give his brother the trade that would make him famous and a strong appreciation for the value of free speech.
In addition to being the original location of the Boston Latin School, the building that stands here now was also the location of Boston’s city hall for over twenty years in the mid 19th century. It has been since known as Old City Hall. The building is a great example of a style called the French Second Empire, which is best exemplified by the Louvre in Paris. The building now houses a restaurant and other commercial businesses.
Old Corner Bookstore
Old South Meeting House
The British fought back against this meeting site in 1775, taking it over, gutting it, and using it to practice horse riding. It was fortunately saved from destruction. There is a great diorama of Colonial Boston inside the building that gives you a great sense of geography of the city.
About a 20 minute walk from here to the waterfront is the Boston Tea Party Museum, which is a bit of a tourist trap located not far from the actual historic event. As much as I want to dislike this museum for its Revolutionary War commercialism (you actually dump tea overboard from replica ships as part of the tour), they give you a glimpse of what the Old South Meeting House was like with a live reenactment. I’ll let you decide though if it is worth $30 per adult to see it though. But I’ll admit... I did it. Huzzah!
Old State House
This building is also where the Declaration of Independence was read for the first time in Massachusetts. You’ll see the balcony from which it was read on the east side, surrounded above on each side by a golden lion and unicorn, signs of the British monarchy. These figures are replicas today since the originals were burned by the citizens in 1776. In 1976, on the two hundred year anniversary, Queen Elizabeth and her husband appeared on this balcony during a Boston visit to speak kind words of the bonds today between our two countries.
The east side of the Old State House is crossed by a single street with two names. It is called State Street on the east side of Congress Street, and Court Street on the west side (the side on which the Old State House resides). In Colonial times, State was called King Street and Court was called Queen Street. The royal courthouse was just a couple blocks up the road on Queen Street in Colonial times. John Adams boarded and practiced law on Queen Street near the courthouse. For anyone who has watched the scene in the HBO miniseries, John Adams, where he rushes to the scene of Boston Massacre, this is the actual location. While it made for great TV, I am pretty sure Abigail and the kids were back at the farm instead of staying in John's boarding house.
The cobblestone marker near the Old State House commemorates the massacre. It has a ring of cobblestones for each of the Thirteen Colonies. The five pointed star represents the five killed in the Boston Massacre, and the six bricks surrounding the star represent the wounded. This memorial has been moved twice since its creation, with its original location being in the center of State State and Devonshire, where the African-American citizen Crispus Attucks was shot, the first death in the American Revolution.
The story that is often overlooked is the trial that followed. To reduce the tensions the royal governor temporarily removed troops from Boston. The eight soldiers were arrested and imprisoned on charges of murder at a nearby jail. The trial occurred at the newly opened courthouse on Queen’s Street (now Court Street, where you stand). The British soldiers were represented by none other than John Adams, who would eventually be a delegate the Continental Congress, signer of the Declaration of Independence, and second President of the United States. The prosecution was represented by Samuel Quincy, a friend of both Adams and John Hancock, who would remain a British loyalist. In the end all but two of the soldiers were acquitted of charges, with the two receiving lesser manslaughter charges.
Faneuil Hall & City Hall
Let’s look back at Faneuil Hall now. The building you are looking was built as a public meeting space in 1761 by a wealthy Boston merchant. There has been some controversy over the name Faneuil Hall since Peter Faneuil made his money in the slave trade. There are also some people who claim the proper enunciation of his name in that era was “Funnel”, which would make this pronounced “Funnel Hall.” Today this building houses various shops, and is more interesting for its history than it is as a place to visit. In the tumultuous 1760s though, this was a popular gathering place to protest “taxation without representation.” But during the British occupation in 1775 this building had been turned into a theater. Note: there are restrooms in the basement if you are so inclined at this point in our walk.
Take a moment now to look north in the direction of the Boston (TD) Garden. When Boston was first settled, this area was a cove, but by 1775 the city had built a half mile long wharf across the cove to turn it into Mill Pond. Benjamin Franklin was known to have fished in Mill Pond during his childhood. In the 1800s this pond was filled in to make room for new development. Most people forget how much of what we think of as today’s Boston came from landfill projects. The following map from 1775 gives a great overview of what the city looked like in Colonial times.
The North End park across the street is the approximate location of the Green Dragon Tavern, which in addition to being Paul Revere’s favorite watering hole, was also the meeting location for the Sons of Liberty. The Green Dragon is where the Boston Tea Party was planned, and where Paul Revere left from on his famous midnight ride.
Paul Revere House
If you get a chance to visit Boston’s Museum of Fine Arts, stop by the American art section and look for John Singleton Copley’s Paul Revere portrait. As you walk around the room of portraits from this period, you’ll notice they all are very formal, making their subjects look like members of the royal family or like famous generals. The fact that Revere was a craftsman sitting for a portrait is by itself unusual, but what is more striking is that he is dressed plainly, does not wear a wig, and has on an unbuttoned shirt and vest. You’ll also notice he holds a silver teapot, a not so subtle nod to his silversmith trade and opposition to British taxes (this portrait was painted a year after tea was taxed via the Townshend Acts). While the tour of Paul Revere’s house is not likely to be the highlight of your tour, at $5 per head it’s probably worth the time.
Old North Church
The tensions were rising quickly in Boston in 1775 when the British government officially declared Massachusetts in a state of rebellion. In response Massachusetts formed its own provincial congress, and by March issued a proclamation that any British forces leaving Boston would be met with resistance. By April 8, with an expected British march imminent, all the leaders of the rebellion except Paul Revere and Joseph Warren left Boston.
But in spite of their best attempts to conceal the planned march to Concord to find and destroy rebel arms, the departure date was well known by the Colonists. As the British troops mustered on The Common to prepare to take boats across the Charles River, Paul Revere instructed two patriots to put two lanterns facing north in the steeple of the church, where they would be seen by waiting eyes on the Charlestown side of the river. While the lanterns were visible for only a few minutes to avoid British eyes, they told the rebels that the British would be crossing the Charles by boat to march to Concord.
The Redcoat march to Concord was expected to be a show of force and not a fight. But when they arrived in Lexington, the local militia refused to disperse, and shots were fired. Most of the arms had already been moved by the rebels by the time the British arrived at Concord, and again their attempt to disperse the militias was met with fire. By midday the British had destroyed what few weapons they had found and turned to head back to Boston. But by then the militias from the surrounding towns had been raised, and they harassed the British column with steady musket fire. By the time the Redcoats reached Boston, they had suffered over 300 casualties. In the morning when they awoke. Boston was surrounded by over 15,000 militiamen, armed and itching for another fight.
Copp’s Hill Burying Ground
Great Molasses Flood
When I first moved to Boston, I thought it odd that the city had so many current and former candy factories. A little sleuthing provided me the explanation: Boston was one of the ports in the slave triangle. This trade that brought slaves from west Africa to the Caribbean, and sugar & molasses from the Caribbean to the Colonies, where they were turned into rum and other products for sale overseas. Although slavery had long since been outlawed in 1919, the molasses trade had continued.
Battle of Bunker Hill
The Colonial militias had gathered around the city like a swarm of angry bees after the Battles of Lexington and Concord. In June of 1775, the Colonial leaders learned the British were going to disperse them by sending troops to occupy the hills surrounding Boston. The Colonists responded by occupying Breed’s and Bunker Hill on the Charlestown Peninsula. As I mentioned at the start of our tour, the Colonists strategic blunder was negated only by British arrogance. Had the British simply sailed around the rebels and landed their troops at the neck, they could have cut off the Colonial troops. But instead the British landed at Charlestown and proceeded to make a frontal assault on Breed’s Hill. It took three assaults before the Colonists, low on ammunition, gave way and retreated from the peninsula. The British victory came at an incredibly high cost: over though 1,000 dead and wounded. This would elicit the famous British General Clinton quote: “A few more such victories would have shortly put an end to the British dominion in America.”
Less than a month later, George Washington arrived to organize a Continental Army, and there was no turning back for the Colonists now. They would either be a free country, or be hanged as rebels. The Revolutionary War had begun.
That’s it. You survived. Thanks for taking the time to go on my personal walking tour of Boston, I’m happy to make updates to this if you provide feedback. I hope you enjoyed.