My Boston Freedom Trail Tour

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

Since I live north of the city, I always start my tour on 93 South as I near the Zakim Bridge. If you look to your left while driving, you will see the Bunker Hill Monument, which is the tall white obelisk protruding from a hill in Charlestown. The best viewing area is between exit 26 and Bunker Hill Community College. For anyone who has been to Washington DC, this structure will look suspiciously like the Washington Monument. But in truth the Bunker Hill Monument was completed in 1842, and work on the Washington Monument didn’t start until 1848. Thus next time you go to Washington DC, make sure to say: “This looks suspiciously like the Bunker Hill Monument.”

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

I like to start my walking tour in the Boston Public Garden at the statue of George Washington. I do this for two reasons: (1) it’s a great place to set the historical context for Boston in the Revolutionary War, and (2) most people forget that George Washington spent almost a year of his life in Massachusetts. You’ll have to cross the busy Charles Street to get here, so make sure to use the crosswalk - anyone that stands between a Boston driver and their destination should be considered at risk.

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

The plaque you are looking at is the former location of The Great Elm. This tree was located in the center of the Boston Common until its death in 1876. Before we tell the story of The Great Elm, it’s worth a little history on the founding of Boston.

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

The visitor center is as good a place as any to talk about the history of the Boston Common. The Boston Common is the oldest public park in America, and there is a case to be made it’s the world’s first urban park (take that London). This area was used for years as a shared cow pasture until overgrazing led to the banning of cows in 1830. During the Revolutionary War the Common was used to house British soldiers, and the troops that marched on Lexington and Concord mustered here before boarding boats to cross the Charles River. A year later, after the British evacuated the city, The Common would be used for drills by George Washington. There is an old story that Washington once broke up a fight on the Boston Common between soldiers from Virginia and New England. He apparently rode in on his horse, jumped to the ground, and lifted the two ring leaders off the ground by their collars.

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

John Hancock was one of the wealthiest merchants in Boston before the Revolutionary War, and would go on to be an early revolutionary leader, serve two terms in the Continental Congress, become the first signer of the Declaration of Independence (with his “John Hancock” of course), and was elected to be the first governor of the state. The plaque on the iron wall below the west wing of the State House commemorates the location of his house before and after the war. Unfortunately the house was sold and torn down, a mistake that would spur the restoration movement that would save several other historic Boston buildings, such as the Old State House. If you ever find yourself in Ticonderoga, New York, you should stop by the Hancock House to see a replica of this former Boston house. If you ever get an explanation for why the house is there though, please let me know.


The Massachusetts State House

The Massachusetts State House is home to the state legislature and the offices for the Governor. The main building was erected in 1798, becoming the “New State House”. The dome on the top was first covered in copper by Paul Revere, and was later painted in gold. During World War II, fear that the dome could be used as a landmark for German bombers prompted the state to paint it black. Fortunately those German bombers never found their way across the Atlantic to threaten the US mainland, and the dome was later covered in 23 karat gold.

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

Hopefully you watched the movie Glory (1989) before coming here. This monument commemorates the 54th Massachusetts Volunteer Infantry, which was one of the first first all-black regiment in the Union army during the Civil War. Their leader, Colonel Robert Gould Shaw, was the son of a prominent abolitionist family from Massachusetts, who died leading an attack on Fort Wagner in 1863. The monument depicts the march of the regiment down Beacon Street on their way to the war. It’s worth noting while you are here that with all the current controversy over Confederate monuments, it was the Confederate President Jefferson Davis who issued the order that African-American soldiers and their white officers were to be put to death if captured. This is one of many good reasons you won’t find a Confederate monument in Boston, and why it mystifies me that organizations like the United Daughters of the Confederacy would find anything to celebrate in Jefferson Davis.

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.


1st Subway

In 1897 the first subway in the United States opened here in Boston. It had three stations: Park Street (here), Public Garden and Boylston. Over 100K people rode the subway that first day, which provided a way to bypass the maze of narrow and winding streets of Boston that were mostly created from cow paths. There was an article a few years back that claimed there was early resistance to a subway due to the fact people of the time associated going underground with death.





Park Street Church

James Madison was president when the construction of Park Street Church was completed. For years the 217 foot steeple towered over the landscape of Boston. This church was the heart of the early abolitionist movement, and William Lloyd Garrison gave his first major public speech here. It is also the site of the first singing of My Country ‘Tis of Thee. I’ll confess that I usually don’t go inside since you will find - spoiler alert - that it looks just like a church.


Granary Burial Grounds

The Granary Burial Grounds were once part of the Common, and were first used to inter the dead in 1660. The name of the site comes from a building used to store grain that once stood on the location of the Park Street Church. As you walk around you should know that the neat rows of headstones are a modern adaptation, having been rearranged to support lawn mowers after the cows were banned.

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.


King’s Chapel

King’s Chapel was home to the first Anglican Church in Puritan Boston. I’d mentioned previously that John Winthrop and the Puritans were not exactly friendly to other faiths, so the construction of an Anglican Church in Boston marked the beginning of the era of religious freedom in the city and country. While the church dates to the late 17th century, the building that stands here now was built in 1754. Service at this church was attended by many notable people, including George Washington, Paul Revere and Oliver Wendell Holmes.

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

The location of the Benjamin Franklin statue was the site of the Boston Latin School, the oldest public school in America. For all their faults around religious intolerance, the Puritans valued education, and this school was opened in 1635. Five signers of the Declaration of Independence went to school here, including Benjamin Franklin, Sam Adams and John Hancock. While the school is no longer at this location, it continues to educate the children of Boston at its “new” location in Fenway.

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

Believe it or not this Chipotle was the former home of Anne Hutchinson, who was expelled from Massachusetts for heresy in 1637. Anne, a midwife, used to hold regular gathering at her house at which friends and followers would discuss the Puritan sermons of the day. She frequently espoused views that were antithetical to Puritan beliefs, and was eventually expelled from the colony in punishment. After a 1711 fire, the site was rebuilt with an apothecary shop, and has since been preserved. Over the years it was home to a series of publishing companies - thus the name Old Corner Bookstore - and was a regular meeting place for famous authors such as Ralph Waldo Emerson, Nathaniel Hawthorne, Charles Dickens and Henry Wadsworth Longfellow. The next time you watch A Christmas Carol with its famous character Scrooge, you can think of Charles Dickens meeting to talk to authors while on a visit from London. Where else in the world can you can you stand on 400 years of history while eating a beef burrito?


Old South Meeting House

You’ll have to pay a small fee for entry, but I always find the stop at the Old South Meeting House worth it. This building, built in 1729, was the gathering place for Bostonians to discuss the increasingly onerous taxes being levied by the British on its American colonies. In 1773 over 5,000 Colonists gathered here to debate what to do about the 30 tons of tea that sat on three ships in the Boston Harbor. With the passage of the Tea Act, unloading this tea would make the Colonists responsible for a tax they didn’t want to pay without representation in the British government. It was shortly after this meeting that the Sons of Liberty raided the three ships to throw their tea into the harbor in what became known as the Boston Tea Party. Problem solved.

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

The Old State House was erected to replace the wooden Town House that burned in 1711. This building has served many purposes over the year, but few more important than being the seat of the Colonial government of Massachusetts from 1713 to 1776. It was here that the first public opposition to the British government in the Colonies was voiced, and where the House of Representatives defied the royal governor’s request to rescind their opposition to taxes. This resistance would later result in the British government sending two regiments of soldiers to occupy Boston, in what would be known as the Occupation. To this day the city celebrates a holiday called Evacuation Day, which marks the day the British left Boston.

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.


Boston Massacre

The British government sent 2,000 British soldiers to occupy Boston in 1768. Tensions had been steadily rising by 1770 when an altercation between a British soldier and a wigmaker’s apprentice came to blows on March 5th. As the evening wore on, angry crowds gathered in the streets and grew larger and more boisterous. When a group of fifty locals surrounded the offending soldier, a group of eight British soldiers relieved him of duty as the mob threw snowballs and other objects at them. After one soldier was knocked down by a club, the British soldiers started firing, killing five citizen and wounding six others.

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

At this point you should be facing the statue of John Adams in front of Faneuil Hall. Before we get into Colonial history, turn around and take a look at the giant cement monstrosity that is Boston City Hall. This building was finished in 1968 in a style that has been aptly named “brutalism.” It remains to this day one of the ugliest buildings in all of Boston, whose only redeeming factor is that like a really ugly dog, some people actually think it is attractive. The people of Boston are conflicted over what to do with their cement disaster. Most feel it should be torn down and replaced, but some design experts think it should be preserved as one of the best examples of the “brutalist” architecture. I’m in the tear it down crowd. Design experts: take a picture and hang it on your mantle.

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.


Boston Stone

While this deviates from the Freedom Trail, I always bring my guests down Marshall Street on my way to the North End. The cobblestone street and shops always make me feel like I’m transported back to 1770. While you are here, try to find the “Boston Stone”, an engraved stone from 1737 that is embedded at the base of one of the buildings. There has been confusion over the years on the purpose of this stone, but most now believe it was just put there as a poor imitation of the more famous London Stone, a tourist attraction dated to over 1,000 years old.





Mill Pond

The building you are standing in front of is the Boston Public Market. Depending on the day of the week, it’s possible you just pushed your way through the smelly outdoor market to get here. You can think of the Boston Public Market as the upscale, not smelly, indoor version of the market you just walked though. If you have the time, it’s really worth a visit, and includes shops selling products from all over New England.

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

To get here you have to walk through the North End of Boston, which is known as the Italian section of the city. Don’t get distracted by the famous Mike’s Pastries, since many tourists have failed to return to this tour after one too many cannolis. Built in 1680, the Paul Revere House is the oldest structure in Boston. Most people know Paul Revere only for his evening ride to warn the Colonial leaders that the British were coming. But Paul was also one of the community leaders of Boston, and an early patriot. His trade as a silversmith made him well known in Boston. In 1765 he became a member of the Sons of Liberty, a secret society formed to protest British taxation. He was one of the participants in the Boston Tea Party, which boarded three British merchant ships to toss their tea overboard. His most famous contribution though was his “midnight ride” to warn the Colonial leaders that the British were marching on Lexington and Concord.

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

Make sure you walk past the statue of Paul Revere and through the Paul Revere Mall to get to the Old North Church. This is the oldest standing church building in Boston, having been built in 1723. You can get a tour most days for a small donation. Let’s tell the story behind the phrase made famous here: “One if by land, two if by sea.”

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

Copp’s Hill is the second oldest cemetery in Boston, having been founded in 1659. By the time I get here, I am usually all cemeteried-out. But if you stop here, make sure to look for the grave of Robert Newman, who was one of the two patriots who put the lanterns in the Old North Church.


Great Molasses Flood

The plaque in Langone Park commemorates one of the strangest disasters to befall Boston. In January of 1919, a large storage tank filled with molasses ruptured and spilled its contents all over the North End. Giant molasses waves rolled down the North End streets, killing 21 and injuring 150. This fascinating story is told in detail in the book Dark Tide.

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

Most tourists will bail on the Freedom Trail before making the long walk across the bridge and up to Bunker Hill. But if you are persistent enough to make it this far, take the time to go to the Bunker Hill Museum across the street and to climb to the top of the monument. When you get to the top of the monument, look south across Charlestown and the Boston Harbor to where the famous battle occurred.

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.