Walking the Historic Freedom Trail in Boston
Updated: Jun 20
Here's my guide to walking the Freedom Trail in Boston Massachusetts. Boston is an incredibly walkable city, filled with history and iconic landmarks.
One of the best strolls through Boston is the Freedom Trail, where you can visit Boston's revolutionary beginnings amidst a modern cityscape. It's one of the best history walks in the United States.
Though I've been to Boston many times (and lived there), I first formally walked the Freedom Trail a couple weeks ago on a beautiful fall day. I think it's an unmissable experience in Boston, especially for history buffs.
What is the Freedom Trail? + Tips for Visiting
The Freedom Trail is a beloved 2.5 mile pedestrianized walk wiggling its way through historic Boston. It leads you through the 16 major sites and monuments relating to Boston's founding and the Revolutionary War. You follow a designated red brick path, with signs and historical markers along the way.
The trail is the perfect, easily digestible, history lesson. And, best of all, it's impossible to get lost.
The trail begins in the Boston Common, the nation's oldest park, and ends at Bunker Hill in beautiful Charlestown. You can walk the Freedom Trail in either direction.
Charlestown is a bit of a hike across the Charles River, away from most of the Freedom Trail sites. You may consider breaking the Freedom Trail into two days and doing the Charlestown sites separately.
Pick up a map and guide at Faneuil Hall or the Boston Common Visitor Center at the beginning of the trail at 139 Tremont Street. Most of the stops on the Freedom Tail are free, though some charge admission. The Old State House, Old South Meeting House, the Paul Revere House, and Old North Church all require paid tickets. Most sites are open from 9:00 am to 5:00 pm.
You can walk and follow the Freedom Trail on your own. Or you can take a Freedom Trail tour led by 18th century costumed Freedom Trail Players for juicy insider tales of high treason, mob agitations, revolutionary actions, and partisan fights of the American Revolution.
Overview of Boston's Role in the Revolutionary War
You should study up on this exciting period of history before hitting the Freedom Trail. A refresher course will make the walk infinitely more meaningful. Click here for a handy PDF map to examine the trail in advance as well.
In colonial American, Boston was a hotbed of dissent and radicalism. A series of taxes levied by the British were the source of tension: the Stamp Act, the Townshend Revenue Act, the Sugar Act, and the Tea Act. The colonists thought them unjust, while the Brits thought them warranted to pay off debts incurred defending the colonies.
Colonists protested these taxes outside Faneuil Hall. In 1761, James Otis coined the phrase "Taxation without representation is tyranny!" In 1768, the British sent in troops to quell the unrest. In 1770, increased tensions erupted when British troops killed 5 men in what became known as the Boston Massacre.
The 1773 Tea Act was the last straw for the colonists. Britain taxed the colonists but exempted its own company (East India Tea Company) from import taxes.
In their first major act of defiance, the colonists stormed a British ship in Boston Harbor and dumped barrels of tea into the water. That protest became known as the Boston Tea Party. In response, the British enacted the Intolerable Acts, which stripped Massachusetts of self government and judicial independence.
Colonists convened a Continental Congress. In 1775, the first shots were fired in the Battle of Lexington and Concord. The Revolutionary War had begun. In 1775, the colonists failed to prevail but significantly damaged the British cause in the Battle of Bunker Hill.
In 1778, the French allied with the colonists, which turned the tide. In 1783, the Treaty of Paris formally ended the revolution.
Historic Must See Landmarks on Boston's Freedom Trail
Let's go on a Boston Freedom trail walking tour and see all of the cultural sites. You could spend a few hours or the entire day on this endeavor, depending on your own interests and whether you go inside the museums.
Personally, I liked the Granary Burying Grounds, the Old South Meeting Hall, and the Paul Revere House best for a taste of revolutionary history. The Old North Church is also unique for its place in American folklore.
1. Boston Common
Boston Common is the oldest city park in the US, dating back to 1634. In Boston's early days, the park was used for cattle grazing and as a training field for the British militia.
Much like the green in the Tower of London, the Common was center stage in American history. It was used for hangings, duels, and spirited oratory.
Today, the Common's historic green lawn is used as a playground. The Common hosts public celebrations, concerts, Shakespeare plays, and holiday festivals. Speakers like Barack Obama and Martin Luther King Jr. have used the Common to rally New Englanders.
Boston Common is adjacent to Boston Public Garden. I think this is Boston's prettiest green space. So you may want to have a stroll there before you start your Freedom Trail walk.
2. Massachusetts State House
This magnificent Federal style building was designed by America's first professional architect Charles Bulfinch. It was completed in 1798, and is the oldest building on Beacon Hill. The land on which the state house was built was originally owned by John Hancock, a signer of the Declaration of Independence.
The golden dome is one of Boston's defining landmarks. But it wasn't always gold. It began life as a simple wooden dome. In 1802, patriot Paul Revere's copper company was commissioned to cover the dome with copper. In 1874, 24 karat gold leaf was added.
The Massachusetts State House is open to the public. You can take a guided or DIY tour weekdays from 10:00 am to 3:30 pm. Guided tours are approximately 30-45 minutes. You'll learn about the history and architecture of the building and see the House and Senate chambers.
3. Park Street Church
Your next stop is Park Street Church. Founded in 1809, the church was originally nicknamed "Brimstone Corner" because of the fiery sermons delivered on site.
It was also where gun powder was stashed, in the crypt. Its 217 foot white steeple was once the first thing travelers saw when approaching Boston.
Only July 4, 1829, William Lloyd Garrison called for the abolition of slavery from the pulpit. Two years later, the hymn My Country Tis of Thee was sung on the church steps. The Boston chapter of the NAACP had its first meeting at this historic church.
4. Granary Burying Ground
Granary Burying Ground is the most visited cemetery in Boston. It's the third oldest burial ground in Boston, dating back to 1660. And the cemetery is the famous resting place of many famous Patriots, including Paul Revere, John Hancock, and Samuel Adams. The victims of the Boston Massacre are also buried here, in the Adams' family tomb.
The first and largest monument that you'll see is the Benjamin Franklin Monument. No, the great man isn't buried there. But his family is. The monument to the wealthy John Hancock, who helped fund the revolution, is easy to spot as well.
Most people come to pay respects to Paul Revere. His grave is directly behind the Franklin Monument, in the shape of a pedestal. Paul Revere, of course, was made famous by the Henry Wadsworth Longfellow poem The Midnight Ride of Paul Revere. (More on that topic below.)
It's free to enter the graveyard, which is open every day from 9:00 to 5:00 pm.
5. King’s Chapel & King's Chapel Burying Ground
King James II seized the land for this granite church in 1686. He established the first Anglican church in New England. In 1749, the Georgian style chapel was constructed around the original church.
The interior is considered one of the best examples of Georgian architecture in all of the united States. The church houses the oldest pulpit still in use and a Paul Revere designed church bell from 1816.
Next to the chapel on Tremont Street lie the King's Chapel Burying Ground, used by the Loyalists. You'll find the graves of John Winthrop, Massachusetts first governor, and Mary Chilton, believed to be the first women to step off the Mayflower. The grave of Elizabeth Pain has a headstone said to inspire Hawthorne's character Hester Prynne in The Scarlet Letter.
6. Benjamin Franklin Statue
Old City Hall was the site of the first public school in the United States. Benjamin Franklin was one of the school's illustrious alumni.
In front of Old City Hall is the towering 8 foot statue of Benjamin Franklin, one of Boston's most famous sons. It was sculpted by Richard Greenough and erected in 1856. It's said that the left side of Franklin's face is philosophical, while the right side is more whimsical.
7. Old Corner Bookstore
The Old Corner Bookstore, currently under scaffolding, was once the epicenter of Boston's literary life in the 1800s. Here, the nation's leading publisher produced works by renowned authors such as Dickens, Harriet Beecher Stowe, Tennyson, Hawthorne, Emerson, Longfellow, and Oliver Wendell Holmes.
The historic site is now a commercial building, rather a sad fate for such a historic book store. There are no books anymore, just fast food.
8. Old South Meeting House
Built in 1729, Old South Meeting House is the second oldest church in Boston. It's a symbol of the colonial mixture of church and state, one of the nation's most important historic sites. The church sports a massive bronze bell made by Paul Revere in 1801.
Old South Meeting House was used as a meeting place for angry patriots. They held public meetings there when their numbers outgrew Faneuil Hall. Many crucial events leading to the revolution occurred here, including events triggering the Boston Tea Party. In 1773, 5,000 people gathered to hotly debate and protest the British tea tax.
In 1872, the church was slated for demolition. It survived the wrecking ball only with the intervention of wealthy Bostonians who recognized the historic significance of the site. Since 1876, it's been a museum. Inside, you'll find historical exhibits and memorabilia, including an exhibit about freedom of speech.
9. Old State House
Built in 1713, the Old State House is one of Boston's oldest landmarks. It was the seat of the royally-appointed colonial government. It was a center of political and commercial life, even housing a merchant's exchange.
The Old State House played a central role in the revolution. It was the site of James Otis' 5 hour speech against the Writs of Assistance (general search warrants) as an instrument of arbitrary power. In 1770, the Boston Massacre occurred in front of the building.
Today, the Old State House is a museum. Every 30 minutes, a colonial speaker in costume appears providing the audience with details of his or her life in colonial Boston.
10. Site of the Boston Massacre
Right next to the Old State House is a ring of cobblestones that marks the spot where the Boston Massacre occurred on March 7, 1770. In this clash between Colonists and Redcoats, five men were killed when British troops fired (without orders) on tax protestors. Paul Revere dubbed the event a “bloody massacre.”
Among those slain was Crispus Attucks, the first African American to die for the revolutionary cause. In reality, it was the Americans who started the riot. Nonetheless, they became martyrs for liberty, memorialized in an engraving by Paul Revere. The conflict energized anti-British sentiment.
11. Faneuil Hall
Built in 1742, Faneuil Hall was a gift from the wealthy merchant and slave trader Peter Faneuil. It served as an open air market and Boston's first town meeting hall.
Faneuil Hall was a political hotbed, where patriots protested British authority and taxation. Here, Samuel Adams and James Otis gave impassioned speeches. Citizens rallied against the British taxation statutes. Faneuil Hall earned the nickname the "Cradle of Liberty."
In 1806, America's first professional architect Charles Bulfinch enlarged the building. After the revolution, citizens gathered for anti-slavery speeches. Advocates of women rights also gave speeches there.
As a result, Faneuil Hall is the most visited destination in New England. It has an open ground floor serving as a market, a covered assembly room above (the Great Hall), and a grasshopper weathervane atop the roof. In the Revolutionary era, town meetings and ceremonies were once held in the assembly room.
Faneuil Hall Marketplace is the perfect place on the Freedom trail to stop for lunch. You have tons of choices. You can get just about anything here.
Since you’re in Boston, try clam chowder or a lobster roll, the local New England specialties. When I was there, I opted for a lobster roll from Wicked Lobsta.
12. Paul Revere House
The Paul Revere House is the surviving house of the esteemed patriot. Built around 1680, it's the oldest building in downtown Boston, with 90% of the original structure remaining. His rather tiny house was the starting point of Revere's famous Midnight Ride.
Revere was not only a patriot, but also a fabulously successful silversmith, copper manufacturer, part time dentist, and engraver. He was the father of 16 children, 10 of whom survived childhood.
You can tour the house for $5. Though it seems small, the Revere House was considered a "mansion" at the time (according to the tour guide). One mark of Revere's wealth are the stained glass windows, indicating that he could afford to pay for heating. You'll see a state of the art colonial kitchen and bedrooms decorated in period furniture.
13. Old North Church
Old North Church is the subject of American folklore. It was the official launching pad for Revere's famous Midnight Ride.
Revere arranged to have lanterns perched on the steeple warning that the Redcoats were coming. Sexton Robert Newman hung the lanterns. Revere's Midnight Ride is regarded as the event that sparked the American Revolution.
The Midnight Ride has been embellished, thanks to English poet Henry Wadsworth Longfellow's poem entitled Paul Revere’s Ride. Revere did not single handedly warn the Boston countryside of the coming British invasion, as the poem implies. Nor did he shout "The British Are Coming."
Here's what really happened, which is still rather dashing.
On April 18, 1775, Revere and another patriot William Dawes were given the task of riding to Lexington to alert patriots and militia that Redcoats would be marching into northwest Boston. The troops planned to arrest Samuel Adams and John Hancock, who were in Lexington. According to legend, Revere contacted Newman and asked him to hang two lanterns in the Old North Church, indicating that the British would arrive by sea.
Narrowly evading capture, Revere rode from Charlestown to Lexington, warning people along the way that British troops were coming. Other riders (40) joined them to spread the message.
Revere was captured on the road outside Lexington. But his compatriot William Dawes escaped and rode on to alarm the militia in Concord. A group of patriots freed Revere from his British guards, allowing him to help the Hancock family escape.
Aside from the glorious folklore, the church is a creaky wooden wonder inside. Among other things, you'll find the only sculpture of George Washington in his best likeliness. If you go up the stairs to the steeple's bell ringing chamber, on the way you'll find a pair of lanterns thought to be identical to those hung in 1775.
14. Copp’s Hill Burying Ground
Copps' Burying Ground dates from 1659. It was the largest cemetery during the colonial period. Some notables are buried there, including Robert Newman (the man who hung the lanterns), Edmund Hartt (builder of the USS Constitution), and Prince Hall (anti-slavery activist).
Because of its prominent location, the British used Copps to fire cannons at Charlestown across the river in the Battle of Bunker Hill.
Need a snack? Before you leave the North End, stop in at Mike's Pastry or Modern Pastry Shop to sample the best treats and cannolis Boston has to offer.
15. USS Constitution | Old Ironsides
After Copps Burial Ground, you cross the Charlestown Bridge into the beautiful village of Charlestown. It's worth the hike. Down Constitutional Road, you'll find the ship known as Old Ironsides in the Charlestown Navy Yard.
Launched in 1797, Old Ironsides is the oldest commissioned warship afloat in the world. The ship's nicknamed derived from the fact that the British cannonballs appeared to bounce of her impenetrable hull.
The ship that survived British attacks is now a free museum. Tours are led by active duty sailors. You'll go below deck and see what life on a ship was like in the 1800s. There's a lot to absorb here, which may advocate for starting your Freedom Trail hike at Bunker Hill rather than Boston Commons.
16. Bunker Hill Monument
The Bunker Hill Monument is a massive granite obelisk marking the spot of the bloody Battle of Bunker Hill. Taking place on June 17, 1775, it was the first pitched battle of the American Revolution.
Although the British won the battle, the provincial soldiers killed or wounded 1,000 British soldiers. According to lore, patriots shouted "Don't shoot until you see the whites of their eyes!"
You can climb 294 steps up the gigantic granite obelisk for decent views over the city. Across the street from the monument grounds, is the Bunker Hill Museum, housing exhibits about the famous battle.
Boston Freedom Trail Tours
If you want a guided tour, the Boston Freedom Trail Foundation Tour is an excellent way to get more insight and historical details on your trail walk. The 90 minute tour costs $14 and takes you to 11 of the 16 sites. You are led by a "colonist" dressed in period costume.
The Freedom Trail Foundation also offers a MP3 audio file that you can download onto your tablet or phone. This gives you a 3 hour audio tour of the Freedom Trail. The cost is $15. To learn more, click here.
If you plan on visiting a few Boston attractions, the Go Boston Card will save you money. It includes the Boston Freedom Trail tour and entry into some of the historical sites along the trail, like Paul Revere’s House.
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