Boston’s Freedom Trail

Last Updated on December 6, 2023 by

Whether you are a fan of history or not, the Freedom Trail will take you on a great tour of downtown Boston. It is easily walkable in an eminently walkable city. Although most information sites will list the length of the trail as roughly two and a half miles point to point, that distance does not take into account side trips into any buildings or cemeteries, diversions into or around Boston Common, or any other eye catching distraction that may cause you to wander from the path. Consequently, I would plan on an eight to ten mile day if you intend to visit each of the sixteen sites. You should also anticipate a very full day, especially if you become ensnared by any of the food or drink enticements of the North End and Faneuil Hall. As you can see from our route, we walked nearly six miles and never made it across the water to visit Bunker Hill or the USS Constitution.

Tour Stops

Finding your way from along the Freedom Trail couldn’t be easier as there is literally a red brick path (or red paint, because budget cuts) on the ground starting at the Boston Common Visitors Center and continuing every step of the way.

I mention the importance of the brick path because a German family exited the visitor center, map in hand, and immediately turned left to where I happened to be sitting. Left is most definitely not along the correct route. Being the Ambassador of good will that I am, I caught the attention of the father, turned him around and pointed out the path along with some very broken German directions. A hearty thank you and handshake and they were off, score one for me in the good deed column. It is possible the visitor center staff does not emphasize the red brick path enough, or perhaps there was a language issue, but the moral of the story here is to pay attention to your immediate surroundings and you will safely find your way. Also good life advice, actually.

The Freedom Trail was conceived in 1951 and by 1953 40,000 people were using the trail to experience the roots of Independence. Today, approximately four million people visit Boston’s signature tourist experience. Seventy years later, the majority of the sites remain free, although the Old South Meeting House, the Old State House, and the Paul Revere House charge a nominal admission fee.

Boston Common

The natural starting point and southern terminus of the trail is Boston Common. Although only 50 acres in size, when coupled with Boston Public Garden right across Charles Street, an argument could be made for spending a day just in these two locations. The Parkman Bandstand, reminiscent of a Greek Temple, was places in 1912 in honor of benefactor George F. Parkman who established a trust to maintain the park. There is also a variety of artwork including the Brewer Fountain, the Soldiers and Sailors Monument, and the Boston Massacre Memorial.
The newest piece, The Embrace, commemorating Martin Luther King Jr. and Coretta Scott King, was unveiled on January 13, 2023 at the Freedom Plaza located between the Parkman Bandstand and the Freedom Trail Visitor Center. While I am sure the city of Boston is quite proud of the bronze, this particular juvenile’s mind went straight to the gutter upon seeing it.

The statue is supposed to depict a moment between Dr. and Mrs. King hugging after learning he had won the Nobel Prize, but to me it looks like an image of what happens during sexy time. I am not alone. A quick Google search reveals a wealth of articles reaching the same conclusion as me. But hey, art.

Massachusetts State House

The free tour of the State House is a must do in my opinion. If you’ve never visited any State House, in my experience they are monuments to the stability and permanence the government is supposed to convey. It also projects power, but we’ll leave that sticky subject for a different kind of blog. Suffice it to say, the State House is a gorgeous building of impeccable craftsmanship. Our tour guide was a young intern (I assume) who was very well versed in the history of the building, its construction, and its art. He also managed to get in about four words in the space a normal person gets out one, so we really got our moneys worth.

The State House land was once owned by John Hancock, and the Masonic cornerstone ceremony was led by Grand Master Paul Revere. The interior also contains a fair number of statuaries dedicated to prominent Massachusetts figures, including the Quaker martyr Mary Dyer and JFK.

If nothing else, take a moment to visit the Hall of Flags. The ceiling has a fantastic stained glass dome depicting the original thirteen colonies supported by eight bald eagles. The top of the grand staircase also has a stained glass window containing each iteration of the Massachusetts state seal. The hall is dedicated to displaying each of the flags that have returned from every war dating back to the Civil War.

Not to be confused with the Hall of Flags is the Great Hall, although the mistake would be understandable. The Great Hall is a massive space converted from an outdoor courtyard displaying flags from every city and town in the state. There is also a completely random steam punk style clock dominating the center of the hall. Among many, this is a great photo op spot.

Park Street Church

Construction began in May 1809 and was completed before the end of the year. Not bad for building holding the distinction of the tallest building in the country until 1928.
Surprisingly, the Park Street Street Church was only the second of seventeen already established churches to adhere to the theological doctrine of the Trinity. The other churches were converts to the Unitarian belief, the precursor to the Universalist Church.

Enduring the inevitable dips and sways of any business or church, Park Street Church is still going strong today with services routinely holding up to 2000 people every Sunday.
Unfortunately, the church was closed to the public during our visit.

Granary Burying Ground

The cemetery was originally established in 1660 to alleviate overcrowding from King’s Chapel Burying Ground. Nearly 100 years later, in 1737, a small granary was placed on the site of what is now the Park Street Church and the cemetery became known as the Granary Burying Ground. Interments ceased in 1880, but not before approximately 5000 people were buried here although there are only 2,345 gravestones. Notable Bostonians interred here include Massachusetts governors, mayors and clergymen, and the graves of three signers of the Declaration of Independence: Samuel Adams, John Hancock, and Robert Treat Paine. Patriot Paul Revere, five victims of the Boston Massacre, and near the center of the ground, a 25-foot-tall obelisk for Benjamin Franklin’s parents.

A Bostonian of the day would probably not recognize the site as it sits now. Over the years, gravestones have been rearranged to comply with the modern aesthetic (and allegedly the modern lawnmower), as well as some significant landscaping to include walkways, shade trees and shrubbery.

King’s Chapel and King’s Chapel Burying Ground

Although it would be logical to assume King’s Chapel burying ground is affiliated with King’s Chapel, logic fails in this instance. Established in 1630, the burial grounds are the oldest in Boston and have always been under municipal control. In 1668, Royal Governor Andros seized some of the land to build King’s Chapel and, much like Granary Burial Ground, the name stuck due to proximity.

Also similar to Granary Burial Ground, over time the cemetery has rearranged headstone, landscaped and added walkways to the extent the bodies underneath no longer correspond with the gravestones above.
Name recognition in this cemetery is largely limited to influential Bostonians of the time rather than the giants of the Revolutionary War located at Granary, but there are a few notables. Most interesting to me was Mary Chilton, allegedly the first woman (11 year old girl) to step off the Mayflower and on to Plymouth Rock.

Boston Latin School Site/Statue of Benjamin Franklin

 Established on April 23, 1635, it is the oldest existing school in the United States. Five signers of the Declaration of Independence: John Hancock, Samuel Adams, Benjamin Franklin, Robert Treat Paine, William Hooper attended Boston Latin. It has also had more students accepted to Harvard University than any school in the world. Hard to imagine where the notion of East Coast elites may have gained its foothold.
Directly across the street from the original site of Boston Latin School sits the Old City Hall. Within the courtyard is a statue of Ben Franklin erected to commemorate the 150th anniversary of his birth. Also within the courtyard is a large brass donkey symbolic with the Democratic Party along with a pair of brass footprints facing the donkey emblazoned with elephants and the phrase “Stand in Opposition”.

Old Corner Bookstore

The Old Corner Bookstore was built in 1718 and is Boston’s oldest commercial building. When it was a publishing company, literary masterpieces such as Thoreau’s Walden, Hawthorne’s The Scarlet Letter, Longfellow’s Midnight Ride of Paul Revere, and the Atlantic Monthly. Today, it is home to that nouveau American masterpiece – Chipotle.

Old South Meeting House

The Old South Meeting House is arguably represents the heart of the American Revolution. It was here Samuel Adams gave the signal that sent the Sons of Liberty to Boston Harbor to dump 342 chests of tea into the harbor. The Boston Tea Party, in direct response to England’s unreasonable taxation truly set the Revolution in motion.
In 1872, the building was put up for auction and scheduled for demolition. Fortunately, a group of history minded ladies realized the historical significance of the building and rallied fellow famous Bostonians to the cause. The building has since been open to the public as a museum and meeting place since 1877.
The Old South Meeting House charges $15 per adult (reduced rates for seniors and children). Purchasing a ticket here also grants you admission to the Old State House.

Directly across the street from the Meeting House is the Irish Famine Memorial in Readers’ Park. There are two statues, one depicting a starving family in mid 1800’s Ireland contrasted with a wealthy and prosperous family of Irish immigrants to America.

The statues are meant to convey the great potential of American freedom and opportunity. While the memorial was built specifically to recognize the Great Potato Famine in Ireland, certainly the theme applies to any immigrant from any country.

Old State House and Boston Massacre Site

On July 18, 1776 Bostonians gathered at the Old State House to hear the reading of the Declaration of Independence for the first time. The occasion was far different than six years prior when British soldiers killed five and wounded many others. The Boston Massacre marked the first blood drawn in the American Revolution.

The balcony, certainly one of the most photographed in Boston, is where the royal governor, appointed by the King of Great Britain, held his office in the building until 1775. The balcony’s elevated position and commanding view of King Street served to highlight the governor’s stature as surrogate for the crown. The Lion and Unicorn, royal symbols of the King of Great Britain, adorn the main façade facing the public square further reinforcing England’s hold of the colonies. It was fitting then, Bostonians heard for the first time the Declaration of Independence, announcing the birth of a new nation from the very same balcony.
The Old State House charges $15 per adult (reduced rates for seniors and children). Purchasing a ticket here also grants you admission to the Old South Meeting House.

Faneuil Hall Marketplace

If you do nothing else on your visit to Boston, Faneuil Hall and the adjacent blocks are must see locations. It also naturally happens to be one of the most tourist dense spots in town. Crowds aside, here you can get your history fix, do some serious shopping, and then eat, drink, and be merry until the wee hours.

Faneuil Hall

Faneuil Hall was a gift from Peter Faneuil, who woke up one morning to become one of the wealthiest merchants in Boston after the passing of his uncle Andrew. Peter expanded upon that wealth largely through involvement in the slave trade. Although not controversial at the time, Bostonians of today have naturally begun efforts to rename the hall due to this association.

Faneuil offered to personally fund the building, creating a central marketplace in the heart of Boston along with a meeting hall on the second floor. For nearly eighty years the governing of Boston was conducted out of Faneuil Hall until the city population finally grew to such a size that a governor and alderman needed to be elected and moved into the newly constructed City Hall. The government maintained control of the hall and it has been an active locale for meetings, protests, and debate right up until present.

Quincy Market

Not to confuse things for the tourists, Quincy Market is actually part of Faneuil Hall Marketplace. It is the building directly behind Faneuil Hall. These two buildings along with the flanking South Market and North Market comprise the complex formally known as Faneuil Hall Marketplace. In 1823, the mayor of Boston, Josiah Quincy, decided he didn’t like looking at the peons hawking their wares outside the boundaries of Faneuil Hall. By this time the hall was so popular there was no longer room to accommodate all of the vendors. Speeches were made, committees were formed and gnashing of teeth ensued until an expansion was approved and ultimately named after the mayor – largely because he got the job done without the use of taxes. The formal name became the Faneuil Hall Marketplace but everyone still calls it Quincy Market.

Today, the three buildings house hundreds of shops with an eclectic mix of old establishment, new independents, and of course the requisite mix of the larger franchises.

Street Performers

Street performers are definitely a significant part of the experience at Faneuil Hall. This isn’t a situation where you might see someone performing, rather, you should be surprised if they aren’t. Performances are everyday from 11Am to 9PM and are vetted though an application process in order to ply their craft. You will see any manner of entertainment from acrobats, magicians, musicians, singers, and even the odd escape artist! Crowds gather quickly for every performance, so don’t stand around wondering what’s going on, get right up on one of the cones they put out to form the perimeter. I have typically seen performances in the space between Faneuil Hall and Quincy Market, but I understand they also occur near the statue of Samuel Adams in front of Faneuil Hall.
A quick note on the Samuel Adams statue. The statue was designed by Anne Whitney in 1876 after winning a contest in which Congress asked for submissions for prominent figures of each state to be placed in the US Capitol. Many would believe John Adams was the natural choice because, you know, President, but Bostonians chose Sam because, you know, beer. The marble statue proved to be so popular Bostonians had it replicated in bronze and placed in front of Faneuil Hall.

While you are in the area

While you are at Faneuil Hall, there are two iconic Boston locales that should not be missed even if they are not technically Freedom Trail sites. You won’t need to depart the trail and they are well worth your time, especially if you are in need of some caloric intake with a tasty beverage to wash it down.
The Union Oyster House is easily the oldest restaurant in Boston and among the oldest in the country. The building itself dates to the 1700’s while the restaurant has been established since 1826 and designated a national historic landmark in 2003. You can still get a half dozen, but it’ll run you. I’d recommend the clam chowder instead, you are in Boston after all.

The Bell in Hand bills itself as America’s oldest tavern, established in 1795. There is some controversy among purists, however, in that the tavern was relocated to its current location but brought the original bar to the new digs. No matter, it’s damn old, and holds plenty of Revolutionary history within its walls. And, on the definite upside, the tavern now sells more than just ale as was the case when it first opened.

If you need some sobering up after your libation, take a slight detour from the trail to visit the New England Holocaust Memorial.

The Memorial is designed around six luminous glass towers, each reaching 54 feet high, and each lit internally from top to bottom. The number six has many meanings here: the millions of Jews killed in the Holocaust; the names of the six main death camps; a row of memorial candles; and the six years, 1939-1945, during which the infamous “Final Solution,” the most deadly phase of the Holocaust, took place. In addition, millions of numbers are etched in the glass, representing the infamous tattoos inflected on many of the victims’ arms.

https://www.nehm.org/the-memorial/design-of-the-memorial/

Full disclosure, here is where the wheels began to come off for us. By this time, we had been enjoying the trail for a little over four hours and hunger was becoming a factor. (We didn’t take own own advice and stop at either the Bell in Hand or The Union Oyster House on this particular visit).

Paul Revere House

The Paul Revere House is another along the trail that charges admission. For $6 you can take a tour of the small home, but it has been completely restored to replicate what it may have looked like at the time. After acting as a boarding house, candy store, cigar factory, Italian bank, and vegetable and fruit business, interior restoration was pretty extensive.

Restoration aside, the home is still standing and has become a national historic landmark. It is the oldest building in downtown Boston and one of the few remaining 17th-century dwellings to survive urbanization.

Old North Church

Being the oldest church in Boston alone would probably qualify the Old North Church for entry onto the Freedom Trail, but its true claim to fame comes from a much more specific event in history. Legend tells us on April 18, 1775, Robert Newman and Capt. John Pulling, Jr. climbed the steeple and held high two lanterns. The infamous signal, ‘One if by land, two if by sea’, from Paul Revere let colonials know that the British were marching to Lexington and Concord by sea and not by land. The American Revolution was begun in earnest.

By the way, don’t be fooled by St. Stevens Church trying to steal the glory. They are very close to another and are remarkably similar. Plus, from many vantage points in the North End, it would appear St. Stevens is the tallest steeple in the area. A coincidence? I think not. I believe it is a clever ruse to prevent you from completing the Freedom trail by dazzling you in the North End’s maze of eateries.

At this point on this particular trip, hunger won out and we elected to pass on the last three stops. Although we have visited these last three sites previously, the following accounts are drawn from internet research and past personal experience.

Copp’s Hill Burying Ground

The last cemetery along the Freedom Trail, Copp’s Hill is more of a working man’s cemetery. Copp’s Hill is primarily comprised of artisan’s, merchants, and craftsmen who lived in the North End. The previously mentioned Robert Newman of lantern fame is also buried here.

Bunker Hill Monument

The combined forces of Massachusetts, Connecticut, and New Hampshire militia were defeated at the battle, but they inflicted massive casualties on the British. The divorce was official and the American upstarts proved they could hold their own against the superior British forces. It was also at this battle the phrase ‘don’t fire ’til you see the whites of their eyes’ was uttered, urging the militia to conserve their powder and maximize the damage. From this point forward, the militias truly began their transformation into what would become the Continental Army.
Perhaps the best part of the history of this battle is that it didn’t actually occur at Bunker Hill. Probably my schadenfreude in play. The actual battle was fought on Breed’s Hill. Orders were given to Colonel William Prescott to fortify Bunker Hill, but he chose the lower Breed’s Hill instead without explanation. The British also apparently had the two hills incorrectly labeled so everyone met up at the wrong place at the right time.

USS Constitution

Among the many famous stops along the Freedom Trail, ‘Old Ironsides’ is surely the most famous and fittingly the finale of your day. (Assuming you didn’t quit when we did.) While the USS Constitution played a vital role in the War of 1812, it got off to a pretty poor start. First of all, it took three tries to successfully launch it after construction before they finally got it right. A scant three years later it was already mothballed. However, it was pressed back into service during the Barbary war and five years later at the outset of the War of 1812 it would finally achieve glory. In August of 1812, two months after the US declared war on Great Britain, the Constitution defeated the HMS Guerriere. British cannonballs appeared to bounce off the ship earning it the nickname ‘Old Ironsides’. Four successful cruises later and the USS Constitution was the most famous ship of the war.
Tours of the ship are free of charge and operated by the US Navy. The museum is a suggested $15 to enter.

North End

Boston’s North End is a glorious feast for the senses. Restaurant after restaurant boldly proclaiming their presence in neon or subtly tucked into a tiny side street, you simply cannot go wrong here. Unlike the significant reduction of Italian communities in other major cities like Baltimore and New York, Boston’s version of Little Italy has maintained its presence and vibrancy. It’s hard to say whether or not the relentless allure of a fabulous meal made us more hungry or the fact that we were hungry made everything look fabulous, but it didn’t matter – our Freedom Trail tour ended here this time around.

For this trip we chose to eat at Ciao Roma for no other reason than the outdoor seating. The weather was absolutely perfect to sit in the shadow of Paul Revere’s house, enjoy a delicious cocktail and a wonderful meal. The arancini was certainly better than average but the gnocchi was hands down the best I have ever had and I spent six months in Vicenza. The cocktail selection was small but the four drinks we had we excellent. Side note – enunciate clearly when you order. Angela ordered a Boston because it comes up as one of the most popular Massachusetts mixed drinks and got a Moscow Mule instead. Apparently a Boston is not as popular as the TasteAtlas would like to believe. The Mule was prepared perfectly though, so we moved on without complaint and a little bit of laughter.
Finishing of your perfect day leaves only dessert.

While it is possible to get dessert from the restaurant you chose, why not embroil yourself in the great Mike’s vs. Bova vs. Modern debate. For anyone familiar with the Gino’s and Pat’s rivalry in Philly, this is the pastry equivalent. You absolutely cannot go wrong with any of the options, but if you head to Mike’s or Modern bring cash, they don’t take credit. And yes, this is a 2023 post. For my money, Mike’s portion size dominates the competition but quality among the three is up to your particular taste. Don’t limit yourself to just one, where’s the fun in that?