A History Major's Guide to Boston's Freedom Trail

Looking forward to exploring Boston's Freedom Trail? Check out these tips and tricks and you'll be saving, time, money, and effort, while learning a fair bit about our country's founding!

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Looking to learn some history on
​Boston's Freedom Trail?

Quincy Market, Boston (stock)

Boston is one of America's most historic cities, and, unsurprisingly, over the years, they've certainly gotten this whole tourist thing down to an art.

As many of you know, I was an Early American History Major at The College of William and Mary, which essentially means I majored in colonial historical attractions at Colonial Williamsburg (which, incidentally, is lovely if you haven't visited). I served a volunteer tour guide in one of our historic buildings, The Wren Building​, the oldest academic building in continuous operation in the U.S.

So, let's just I was incredibly excited for our trip to Boston, and allotted an embarrassing amount of time to explore the Freedom Trail. Let's take a historic stroll down Boston's Freedom Trail. Along the way, I'll share some tips and tricks to help you learn more and avoid unnecessary crowds and stress.

Planning a trip to Colonial Williamsburg? Check out the Avoidable Mistakes Tourists Make in Colonial Williamsburg

History of Boston's Freedom Trail

Fanueil Hall (stock)

As a city, Boston has done an excellent job preserving its history over the centuries. Luckily for all of us, many of the sights that modern tourists want to visit, surrounding The American Revolution, are focused in a walkable area in the heart of downtown Boston. The city has continued to grow and thrive, with its core in relatively the same area it's historically been, just growing up around, and embracing, these historic monuments. Boston reminds me most of London of any American city I've visited - with narrower streets in the densely packed historic center, and historic monuments intermingled with modern buildings. And, coming from me, that's no small compliment.

In the 1950s, a Bostonian journalist had the foresight to unite Boston's historic sights around a pedestrian-friendly walking trail. Since then, the allure of The Freedom Trail has only grown, including the addition of Boston's Black Heritage Trail, which runs a similar route, uniting destinations pivotal to Black history in Boston and the struggle for freedom throughout the country.

Boston's Old State House, surrounded by new buildings. The Freedom Trail.

Boston's Freedom Trail Tips for Tourists

Now, let's talk through a few logistics that people tend to be curious about when preparing for a trip to Boston, especially one focused around The Freedom Trail.

Boston Freedom Trail Hotels

First things first - where to stay! I couldn't have been happier with our stay at the Hilton Downtown/Fanueil Hall. A fairly high-end selection, right in the heart of things, the Hilton really had everything we needed. I was particularly impressed with the dining options, as both their restaurant/bar (Fin Point Oyster Bar & Grille) and newly renovated coffee shop were excellent. And...it's next door to not one, but two Dunkin Doughnuts. 

How long does it take to walk the Freedom Trail?

The Old North Church (stock)

The entire Freedom Trail is two and a half miles, if you walked it all in one shot (which I wouldn't recommend). However, remember that this impressive distance includes traveling all the way up to the Bunker Hill Monument, which is farther away from the grouping of the sights, across the Charles River. My approach, as ever, is to see what you want to see, spend your time efficiently, don't worry about seeing it all, and be sure you're understanding the big picture historically.

I divide the Freedom Trail into three sections:
First, the area around Boston Common and the Granary Burying Ground, second, the North End, and third, the Bunker Hill Monument on the other side of the Charles River. The North End has more to see than the other two. If you start down at Boston Common and walk to the North End, it's worth taking a quick Uber/cab up to Bunker Hill to ease your inevitably suffering feet! Personally, I'd do it in two days - one day covering that southern portion (Boston Common, etc. and maybe also seeing Beacon Hill and some other non-Trail areas) and one day in the North End, and venturing up to the Bunker Hill monument, if you wish.

The Freedom Trail wiggles its way through Boston and there are many other things to see beyond just the sights highlighted on the Trail itself. Also, the Trail is so open-ended, and you can spend as much, or as little, time in each spot as you wish - or skip spots - that you could see what you want to see in a day, if you're a big walker and don't do everything.  

So take your time, be reasonable with your walking expectations, and enjoy your experience.

Dealing with crowds on the Freedom Trail

Boston's Freedom Trail - Quincy Market. It's usually more crowded than this! (stock)

One of the important realities of the Freedom Trail, and of course any major tourist destination, is dealing with crowds. There's to way to "beat" the crowds, as people are clamoring to see the area, just as we are!

Crowds are a fact of life in any major tourist attraction, and they're especially noticeable here, as they stand out starkly from the Bostonians going about their daily lives. Depending on the time of year, the crowds are certainly manageable if you're prepared for them and follow a few simple tips to make things more enjoyable for yourself.

Explore the Freedom Trail
​in the morning

All 3 days that I walked the Freedom Trail on my most recent trip, the mornings were by far the most enjoyable time to experience the walk.

Of course you'll have to be mindful of when sights open, but get going as early as is reasonable and plan to take a long lunch, when crowds really start to surge. Remember that a lot of sights close at 5.

Walk on the other side of the road
​from the red bricks

I'll admit that this feels like a silly tip, but honestly, it's a bit of a life-saver.

The Freedom Trail is a physical, thin line of bricks that snakes around Boston. It's not hard to follow, you'll have a map (either physically or on your phone), and it's incredibly easy to see where it's going, as you can just follow the people in windbreakers and other people with maps who clearly aren't walking to work.

If you want to be seriously less stressed, walk on the opposite side of the road from the actual red brick line. Everyone wants to walk directly on the bricks and that side of the road can get a bit jammed. Especially in the North End, the sidewalks get more narrow, the crowds increase, and that brick path is *packed.*

​Give yourself some breaks
​from the Freedom Trail

Not only to avoid crowds, but also to experience more of Boston, don't forget to veer off the Freedom Trail every now and then, if only to snap some quick pictures!

How to save money on
​the Freedom Trail

Boston's Freedom Trail (stock)

You don't have to do it all. And, frankly, there's really no need to enter every, single, sight on the entire Freedom Trail.

Figure out in advance which sights are most important to you and skip those you aren't as interested in. Or, alternatively, if you reach a sight and it's crowded with tour groups, put it to the side and come back to it later, once the group has left. The large number of people on guided tours adds to the general crowded feeling of some of the attractions, so if you can ease that, it'll make your experience more enjoyable.

Additionally, I will note that there are 3 public meeting houses on the Freedom Trail (one pictured above). As they all played a very important role in Boston's rise to power and the movement for independence from Britain, it makes sense (New Englanders loved nothing more than gathering). That said, the Old South Meeting House and the Old State House are 2 of the 4 places that charge admission (along with Paul Revere's House and, recently, The Old North Church). If you're looking to cut down on cost, consider entering only Faneuil Hall, which is free, will give you your public meeting house vibe and history, free of charge, and is probably sufficient for you to get the idea. I would choose The Old North Church and Paul Revere's House over adding a second or third meeting house to your agenda.

What to wear on the Freedom Trail?

Ah the million dollar question! Well, you'll certainly be doing a lot of walking, so be sure to bring some *very* comfortable shoes. And, of course, don't let this trip be the first time you've worn them! Other than that, please check out my full post, What to Wear in Boston.

How do I buy tickets for the Freedom Trail?

Strangely, Boston has not opted to create a London-Pass-style "entry to all the sights" card that you buy in advance. This is likely because the vast majority of the sights do not charge admission. At those that do, occasionally long lines can form, but often tour groups have paid in advance, which helps with the bottle necks.

​You can, however, opt to take a tour through The Freedom Trail organization itself, should you wish!

Eating and Drinking on the Freedom Trail

The Bell in Hand Tavern on The Freedom Trail

We all know I love a good pub, and I was pleasantly surprised with our lunch in the North End, The Bell in Hand. Named for the owner's sideline - serving at Boston's town crier for 50 years, and purporting to have gotten its start in 1795, its scenic location  gets a visit to the North End off on the right foot, with narrow streets and a cozy, historic vibe.

The Bell in Hand, Boston

Located right on the Freedom Trail, of course I was a bit worried it'd be over priced and terrible. But my good was great, service was quick, and we were back on our way, quick as a flash!

Water and coffee on Boston's Freedom Trail

Never fear - The Freedom Trail is packed with Dunkin' Doughnuts (now just "Dunkin'") aplenty, a mainstay of Boston. Bostonians just can't seem to get enough of this place, and I will say, the coffee is delicious.

​Pro tip: order a small coffee. Many places on the Freedom Trail (rightfully) don't allow beverages inside, so you might as well finish it off before you go in.

Additionally, don't forget to bring your own water bottle for your adventure, especially in summer. Though plenty of places sell water, it doesn't come cheap, and we all know thirst strikes when there isn't a bottle to be had!

Books to Read Before Visiting Boston

• The City-State of Boston: The Rise and Fall of an Atlantic Power, 1630-1865, Mark Peterson.
• The Revolution Trilogy, Rick Atkinson.
• 1776, David McCullough. A sweeping overview of the entire year and the causes of the Revolution, McCullough's Pulitzer Prizer will get you the background you need. It's not only focused on Boston, but nor was the Revolution, no matter what you're led to believe on the Freedom Trail ;)

Movies to watch before visiting Boston

• John Adams miniseries - one of my absolute favorites, depicting the life of one of Massachusetts's favorite sons. The portion covering the Boston Massacre is particularly poignant. 
• Glory - the true story of "the 54th" (the Union Army's second all-black regiment) is portrayed with heartbreaking detail. The 54th is commemorated in a stunning relief near the Massachusetts State House.

Freedom Trail Map

First things first! You need that handy map. The Freedom Trail offers a helpful and interactive map, available here. There is also an unofficial app, which you can download in the AppStore.

Freedom Trail Sight: Boston Common

Freedom Trail Itinerary

Let's start our tour at its southern-most point, Boston Common. As the name suggests, Boston Common has been the center of Boston life for centuries. To keep us grounded, the Massachusetts Bay Colony was founded in 1620 with the arrival of the "Pilgrims" from England. It was the *second* English colony in what would ultimately become the USA, with Virginia having been founded in 1607. Don't let anyone try to convince you otherwise! :)

​Unlike Virginia, Massachusetts had distinctly religious motivations, which continued to drive policy making in the colony long after its founding. Puritans practiced a strict form of Christianity, reflected today in unadorned churches where participants sat for Sunday marathon sessions so long they actually took breaks, and were intolerant of other religions in their colony and government. The colony was wealthy and successful, which, along with its historic status, kept it in the forefront of power in the American colonies throughout the colonial period.

Remember my quip about New Englanders loving to "gather" - it is based in fact. Boston Common currently holds the title of oldest public park in the United States, dating to 1634 (it really has no competition to speak of!). It contains everything, from a graveyard, Central Burying Ground, to a "frog pond."

Boston Common is a great starting point for your adventure on the Freedom Trail, and it's the meeting point for many tours, if you're taking one! Take as much time walking around as you wish. It's quite large, so don't wear yourself out just yet!

Freedom Trail Sight: Granary Burying Ground

Not far from Boston Common is the Granary Burying Ground, dating to 1660. Boston's third cemetery, it reached the height of its popularity during the life and deaths of the city's Revolutionary heroes and is therefore the final resting place of most of the Bostonians you learned about in school, including John Hancock and Sam Adams. Adams, ever the firebrand is buried next to the 5 victims of the Boston Massacre, at his request. It's hard to miss John Hancock's massive monument, to the far left of the cemetery. Robert Treat Pain is also buried here - a signer of the Declaration of Independence whose name, unfortunately, has not enjoyed the enduring fame of the others'.

And, of course, this is your first (of many) Paul Revere sights! His modest stone is straight to the back of the burying ground.

The Franklin monument in the center is actually Benjamin Franklin's parents. Franklin was born a Bostonian, though he became famous for his connection to his adopted hometown of Philadelphia. The new, massive, stone replaced the original in 1827.

​Don't be fooled by the symmetry of the cemetery - the stones, but not their honorees, were moved in the Victorian era for maintenance reasons, and because Victorians liked everything neat and tidy. 

I remember tour guides always telling curious tourists in Colonial Williamsburg that the graveyards were "full" even if the stones had worn away. The same is true here.

​A deeply horrifying story I picked up while researching: in 2009, a tourist discovered a previously unknown grave in the burying ground...when she fell into it. Luckily for her, she only fell into the staircase into the tomb, and came out unharmed, but I'm still beyond freaked out about it. It's true - there are articles about it.

Paul Revere's Grave

Samuel Adams's Grave

John Hancock's Grave

Freedom Trail Sight: Boston Massacre Site

As you continue North, along the Freedom Trail, you'll come upon the Old State House and the site of the Boston Massacre. The Massacre site is marked by a large plaque on the ground outside the State House.

It was here, on a chilly night in 1770, that a confrontation between a crowd of Bostonians and the British troops stationed outside the Boston Customs House led to the discharge of weapons, without orders, and what would ultimately be deemed the first (5) deaths of the American Revolution. The aftermath was in many ways more interesting than the event itself, with John Adams taking the case in defense of the troops, in spite of widespread Bostonian opposition to his decision. Ultimately, two of the six soldiers were convicted of manslaughter and given small sentences; the others were acquitted. The victims are buried in the Granary Burying Ground that we discussed earlier, next to Sam Adams, at his specific request.

Paul Revere's famous engraving of the "Massacre" horrified colonists up and down the eastern seaboard and served as literal flash point of the growing tension between the colonies and the mother country.

After a few minutes of contemplation and dodging tour groups, it's time to move along!

Freedom Trail Sight: Fanueil Hall 

It's time for my recommended meeting house of choice, and one of the most visited places in the United States, the historic Fanueil Hall. Named for slave trader Peter Fanueil, who built it at his own expense and donated it to the city of Boston (and, naturally slapped his name on it), it has a complicated history. 

​Since its opening in 1743, Fanueil Hall has burned almost entirely, been hugely renovated, and played host to innumerable speeches on every significant topic in US history, from our separation from England, to the end of the slavery, and has been the sight of announcements by a number of politicians, from Massachusetts-based to US presidents. 

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It has an interesting format, echoing our English cousins, with the open market on the main level and the convention space on the top (pictured here).

With its massive numbers of tourists, the blocks around Fanueil Hall are one of the most "touristy" areas I've ever experienced. In fairness, as my husband reminded me, even The Louvre is attached to a shopping mall. No need to linger in this area unless there's something here that appeals to you specifically.

Freedom Trail, Part II: Boston's North End

 It was in the North End that many of the activities surrounding the Revolution were centered, and here that we will find the oldest home in Boston!

Now we're moving from what is now largely the financial district into the former Italian area of town, and the original heart of Boston, and the oldest continually inhabited area of the city, Boston's North End.

Freedom Trail Sight: The Paul Revere House

​Revere lived a full life in this house - making it to the ripe old age of 83, and fathering 8 women, with two wives (bringing the total to 16!!)

Freedom Trail Sight: Paul Revere Mall

​The first sight you'll want to visit in the North End is the home of Paul Revere, the silversmith/engraver famous for risking his life riding through the countryside to warn the townspeople of the impending British invasion, in 1775. 

Paul Revere House, Boston

This ultimately led to the first battles of the Revolution, north of Boston, at Lexington and Concord. His ride was made famous throughout the US with Longfellow's poem, Paul Revere's Ride, in 1861, leading up to the centennial of the Revolution.

This home was old when Revere purchased it, having been built in 1680 (and rebuilt after a fire). It's a modest dwelling by modern standards - essentially just 3 rooms you can really tour, but with multiple floors and separate areas for the various functions of life, he was living large for his time, especially given his day job as a tradesman. According to the foundation that runs the home, 90% of the structure is original to Revere's time, as are many of the furnishings.

Paul Revere Statue in Paul Revere Mall, Boston

Now we journey on, continuing the tale of good ol' Paul Revere, to the Paul Revere Mall, featuring a statue of Revere, resplendent on horseback, with the Old North Church in the background.

The Mall is surprisingly tranquil, given the throngs of tourists, especially in the fall with a cup of Dunkin! The brick walls surrounding the statue commemorate some of the North End's favorite sons (hard to believe anyone lived there aside from Paul Revere - but I promise, they did!). 

One of my favorite plaques commemorates The Salutation Tavern, meeting place of Boston's famed Committee of Safety, and location in which the Boston Tea Party was planned. If you ever doubted our status as a previous British colony, commemorating pubs on plaques will certainly remind you!

Plaque commemorating The Salutation Taverrn and The Green Dragon Tavern, Boston, Paul Revere Mall

Freedom Trail Sight: The Old North Church

One of Paul Revere's destinations on that midnight ride was the famous Old North Church, which is our next destination. It was here that Bostonians hung the famed "two lanterns," in the "one if by land, two if by sea" we've all come to know! They expected the Brits to come by land, so it was a bit of a surprise when not one, but two lanterns were set ablaze atop the church.

​Today, the Old North Church is a gorgeously preserved place to learn about colonial American religion, with restored pews and helpful tour guides (though you're welcome to explore on your own terms). It does now charge a small entrance fee.

Interior of the Old North Church

It is today an Episcopal church, the US-version of the Church of England, and you will see many similarities to Bruton Parish in Colonial Williamsburg, if you're visited.

Interior of the Old North Church

Interior of the Old North Church

Your entrance fee to the Old North Church also allows you to visit its charming garden - and take a quick respite from the churning tourist track. If you're facing the entrance to the church, the garden is around the church to the left.

Freedom Trail Sight: Old North Church Garden

Freedom Trail Sight:​ Copp's Hill Burying Ground

The final sight on our tour of Boston's Freedom Trail is Copp's Hill Burying Ground (we're all about those cemeteries!), which was a personal highlight for me. It's older than the Granary Burying Ground we visited earlier this journey, and was the city's second cemetery, founded in 1659.

Some graves in Copp's Hill Burying Ground are incredibly old, and many contain my favorite depictions of age - "around X years." Close enough! You get a lovely view of the River, if you stroll around.

Thanks so much for stopping by!

Hope you have a fabulous trip to Boston and enjoy walking in the steps of the Founding Fathers on Boston's Freedom Trail! Let us know your tips when you get back! And don't forget to sign-up for the blog newsletter before you go!

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