Best Stops on the Freedom Trail (A Subjective Guide!)

I’ve tackled the Freedom Trail in Boston, Massachusetts, a few times now. I did it once all in one go, then again over the course of a few days. For U.S. history buffs, it’s a must. 

If you only have a cursory interest in the American Revolution, though, you may not want to dedicate as much time to it.

I’d still suggest spending some time exploring the best stops on the Freedom Trail on a trip to Boston, especially if it’s your first time.

While I know what it feels like to be a completionist, there are historic sites along the way that are more interesting than others. 

This guide gets into the essential stops along the Freedom Trail that are either more interesting than the others, more historically significant, or just cooler than the rest. This is then a super scientific list that’s not subjective at all. Let’s get down to brass tacks.

Is that even how that goes? 

What are the stops on the Freedom Trail?

Here’s a complete list of the 16 stops on the Freedom Trail:

1. Boston Common
2. Massachusetts State House
3. Park Street Church
4. Granary Burying Ground
5. King’s Chapel & King’s Chapel Burying Ground
6. Benjamin Franklin Statue & Boston Latin School Site
7. Old Corner Bookstore
8. Old South Meeting House
9. Old State House
10. Boston Massacre Site
11. Faneuil Hall
12. Paul Revere House
13. Old North Church
14. Copp’s Hill Burying Ground
15. USS Constitution
16. Bunker Hill Monument

As far as how to walk the Freedom Trail, it’s 2.5 miles end-to-end. Starting at Boston Common is the most common approach. Walking nonstop, that should take you about an hour or so, but most visitors spend at least half a day going into some of the sites.

You can also book a guided tour that comes with historical insight, beer, or a combo of the two. Check out these highly-rated Freedom Trail tours to explore those ideas:

I’m not sure you came here to walk the whole thing, though. You want the BEST Freedom Trail sites, whether that means they’re extra special in the historical sense or just better than the others. 

This is all our opinion, by the way, so if you want to do the whole thing once and argue with me after, I’ll allow it. It’s a free country, sometimes.

Best Stops on the Freedom Trail

These are all in “order,” as if you were starting from Boston Common. The Common is the officially starting point anyway. It’s marked with the red brick line that guides you through the city’s Revolutionary landmarks, courtesy of the Freedom Trail Foundation.

Boston Common is also centrally located and easy to reach by subway, so it just makes sense that your walking tour will start here.

It just so happens it’s a stop worth making, too, and the first on our list of the best of the best when it comes to Boston’s Freedom Trail.

Boston Common

This is America’s oldest public park, so there’s that. Boston Common dates back to 1634 and has been the stage for all kinds of important moments in U.S. history. 

It was essentially a campsite for British troops during their occupation of Boston. During the Revolutionary period, it was the site of speeches and rallies that got people all in their feelings over independence.

Over the centuries, it’s become a symbol of civic life, hosting abolitionist rallies and civil rights demonstrations. This is where all strolls along the Freedom Trail should begin, not only because it’s the literal start, but because it represents an inflection point.

Massachusetts State House

The Massachusetts State House is one of Boston’s most recognizable landmarks, so you’ll probably pass by its iconic golden dome anyway as you’re walking about the city. Convenience isn’t the only reason I’m including it here, though.

This building was designed by Charles Bulfinch, often called America’s first native-born architect, making it a symbol of early American ideals. 

Perhaps it won’t be covered in scaffolding on your visit. Perhaps it will.

Inside, this is where the state’s House of Representatives and the Senate chambers host debates and mixers (I think?) as they shape Massachusetts law. Honestly, they’ve been doing a decent job, so carry on, folks.

Granary Burying Ground

Historic cemeteries are one of my favorite things, and honestly, I don’t care how that sounds. 

The Granary Burying Ground was established in 1660. Despite how basic it looks upon first glance, it’s the final resting place of some of the most famous names of the American Revolution.

Samuel Adams, John Hancock, and Paul Revere are all buried here, along with victims of the Boston Massacre.

The site offers a tangible, haunting connection to the Revolution. You’re literally standing among those whose words and actions shaped a nation. 

Fun fact: Benjamin Franklin isn’t buried here, but you’ll see an obelisk on the grounds dedicated to his parents. Franklin is buried in Philadelphia at Christ Church Burial Ground.

READ MORE: Love a spooky time? Check out my guide to Salem, an easy day trip from Boston.

Old South Meeting House

This 1729 Puritan meeting house served as the rallying point for the Boston Tea Party. 

On December 16, 1773, more than 5,000 colonists crowded into this hall to debate the tea tax. Samuel Adams gave the signal that night, and the Sons of Liberty marched to the harbor to dump the tea, sparking one of the Revolution’s most iconic protests. 

The Meeting House was a big deal in other ways, too. Outside of a hub for dissent and free speech, it was used as a riding school for British troops. That’s random. Today, you can visit inside to check out its modest exhibit space. 

Note: Try to time your visit around one of their guided gallery walks or tours, as that makes the admission ticket more worth it. You can also nab a combo ticket with the next stop on this list, the Old State House.

Old State House

The Old State House is Boston’s oldest surviving public building. Constructed in 1713, it served as the seat of colonial government and later as the site of dramatic confrontations between the British and colonists. 

We’ll get into that in a minute, but for much of the colonial era, it served as the seat of British government in Massachusetts. This building housed the governor’s offices and the colonial legislature, and its elegant architecture reflected that royal authority. 

Its connection to the Brits isn’t why I’m calling this one an essential stop. The Declaration of Independence was first read to Bostonians on July 18, 1776, from this building’s balcony.

It sparked celebration in the streets, I imagine, firing people up for what was to come.

Today, the Old State House, or Old Provincial State House in some circles, operates as a museum. Exhibits are more extensive than at the Old South Meeting House, so give yourself about an hour to hang out in there if you’re spending time inside.

You’ll explore Boston’s role in shaping democracy, the tension of colonial rule, and the everyday lives of Bostonians during the Revolution. 

Boston Massacre Site

You’ll see this site at the foot of the Old State House, but I thought both deserved their own mentions. They’re also noted separately on the city’s list of stops, so I’m following their lead.

On March 5, 1770, tensions between colonists and British soldiers came to a head when troops fired into a crowd. This was after the soldiers were taunted by a group of colonists who were throwing stuff at them. 

Note: I’m in no way saying you should fire on people for throwing stuff at you, no matter what the stuff is. (I’ve read that it was ice and debris.) I just want you to have all of the information and paint a picture of what set the soldiers off that night. Not everyone can handle the heat of escalating protest activity, as we’ve seen among U.S. law enforcement time and time and again.

Five men were killed in that incident, including Crispus Attucks, often remembered as the first casualty of the American Revolution. Six others were wounded.

Patriot leaders like Samuel Adams and Paul Revere latched onto that moment as a way to fuel anti-British sentiment, as if it wasn’t pretty bad already. Those efforts are considered one of the best examples of early propaganda.

Despite all of that, Boston still held public trials for the soldiers. John Adams defended them, arguing self-defense, and secured acquittals for all but two, who were convicted of manslaughter. 

This spot won’t need a ton of your time, but try to imagine the chaos of that night and how it reverberated far beyond King Street. I find that it’s symbolic of both the human cost of liberty and the fragile line between protest and violence. 

Faneuil Hall

Faneuil Hall, known as the “Cradle of Liberty,” has been a marketplace and meeting hall since 1742. Merchants sold goods downstairs, and the space upstairs became a rallying space for fiery speeches. 

Fun fact: Samuel Adams and James Otis, best known for coining the phrase, “taxation without representation is tyranny,” delivered impassioned speeches here to whip up opposition to British policies.

This was essentially the people’s stage, where grievances turned into collective action. After independence, it continued to be known as a home for free speech. It was a hub for activism as a site of abolitionist speeches and labor rallies.

Today, Faneuil Hall still functions as a public gathering spot, and the surrounding marketplace has evolved into a destination for food and shopping. 

If you’re hungry, this is a decent spot to take a break, as there are quite a few food vendors available. I found it to be pretty touristy, though!

Paul Revere House

Built in 1680, this wooden structure is the oldest surviving house in downtown Boston. (The James Blake House is the oldest surviving house in ALL of Boston.)

You’re likely here for the name on the sign on the front of it, though. This was the home of Paul Revere from 1770 to 1800, including the night of his legendary midnight ride in 1775. 

The house offers a glimpse into everyday colonial life, complete with period furnishings, some of which could use a dusting. There are no photos allowed inside, so you’ll need to take pictures with your mind. 

The house is modest, but it’s certainly pretty cool to walk the same floors that Revere walked with this family, then step outside into the streets where his ride began.

History people, are you all hot and bothered yet?

USS Constitution

The USS Constitution is the oldest commissioned warship still afloat. I’m talking about the oldest anywhere, not just in the U.S. Launched in 1797, she also goes by “Old Ironsides,” a nickname earned during the War of 1812.

Apparently, British cannonballs tossed her way bounced right off her sturdy oak hull, so that’s impressive. 

You can visit her at no charge in the Charlestown Navy Yard, the northernmost stop on the Freedom Trail. We had a good time walking the deck and then going down below to see the cannons and how the men on board lived. Set aside an hour for this activity.

Bunker Hill Monument

The Bunker Hill Monument is traditionally considered the last stop on the Freedom Trail, so that alone makes this one a no-brainer for me.

Perhaps more importantly, it serves as the symbolic climax of the Revolutionary story in Boston. While the USS Constitution is slightly farther north, Bunker Hill represents the first major battle of the American Revolution, fought on June 17, 1775. 

Ending the trail here allows you to walk through Boston’s streets and meeting houses, where ideas of liberty were debated, and end where those ideas were tested.

The 221-foot granite obelisk on this site, completed in 1843, commemorates the sacrifice of the colonial militia. Despite losing the battle, they inflicted heavy casualties on the British army, proving that ordinary people could stand against the British forces. 

We haven’t been to the top of the monument, but you can climb it for a view of Boston and the harbor. To do so, enter through Bunker Hill Lodge. The site does shut down in hot weather, though, for your safety.

More Fun Stops Along the Freedom Trail

Moving from historical site to historical site might sound awesome to you. If you’re like us, though, you need a little something extra along the way to make the journey a little more exciting.

Here are a few bonus stops you can make as you decide on your own list of essential stops on Boston’s Freedom Trail:

• Bell in Hand Tavern: Founded in 1795, the owners claim that this is Boston’s oldest continuously operating tavern. This one is just steps from Faneuil Hall, so it’s an easy add-on after some snacks there.
• The Green Dragon Tavern: The original Green Dragon Tavern was demolished in the mid-1800s. This one is an homage to a pub that was a hangout of Paul Revere and the Sons of Liberty.
• The Institute of Contemporary Art (ICA): We only saw the outside of this one, but even that was impressive. It’s all glass, jutting out onto Boston’s waterfront as if it’s floating.
• Parker’s Restaurant: Located inside the historic Omni Parker House, this is where Boston Cream Pie and Parker House Rolls were first created. Both are delicious, so you don’t have to choose one or the other if you don’t want to.
• Union Oyster House: Established in 1826, this is the oldest continuously operating restaurant in the U.S. Visit the National Historic Landmark for oysters, naturally, or a classic clam chowder.
• Warren Tavern: George Washington and Paul Revere were regulars at this Charlestown pub. It’s older than the Bell in Hand by founding date, as it opened in 1780, but it may not have been open continuously. This isn’t my fight.

READ MORE: Planning trips outside of Boston? Use my guide to the best day trips from the city!

Where to Stay in Boston

We’ve stayed at some real stinkers in and around Boston, but The Revolution Hotel is one we can recommend. Boston isn’t the cheapest city for budget travelers, and prices go up with nicer weather.

If you’d like to browse some, use the map below to get started:

The Boston Freedom Trail is a must for history buffs.

That doesn’t mean you won’t get as much out of it if you pick and choose your stops along the way. If you only have a day in Boston, I don’t know if I’d spend it just on the Freedom Trail. This is a fun city with lots to see, do, and eat.

By all means, do what feels right when it comes to things like this. I don’t want you to feel FOMO over skipping some of the stops, especially coming from a place of having walked the trail twice. If the American Revolution is your Roman Empire, see all of the stops!

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