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“Listen, my children, and you shall hear / Of the midnight ride of Paul Revere.” We grow up learning stories of the American Revolution, of secret meetings in taverns, throwing tea into the harbor, and warning a rebellious militia that the British are coming. All these events happened in Boston, and you can explore them as part of Boston’s Freedom Trail! I went there on a solo trip last fall, so here’s how you can too.
What is the Freedom Trail?
The Freedom Trail is a 2.5 mile walking trail marked on the streets of downtown Boston that connects important historic sites. There are 16 official sites on the trail, most of which relate to the American Revolution. The trail starts in Boston Common and runs through the North End, then across the Charles River to the Bunker Hill Monument. It’s marked by a double row of red bricks in most places.
It’s certainly possible to walk the Freedom Trail in one day if you’re going for an overview. If you want to actually spend time exploring the sites, I recommend splitting it over two days. My strategy was to take a guided tour one day and then return the next day to visit a few sites in depth.
What are these 16 sites we’re talking about? Most places relate to the Sons of Liberty, a group who organized the resistance against the British government that led to the American Revolution. You’ll see the site of the Boston Massacre that turned public opinion against the colonial government. Later, you’ll see the church where the Boston Tea Party was organized and the other church where two signal lanterns were hung to warn the patriot militia that the British were coming. “One if by land, two if by sea…” you remember, right?
You’ll also find some places related to Boston’s early Puritan settlers and some later sites like the USS Constitution related to the early years of the USA.
Read below for a list of my favorite sites.
The Freedom Trail With a Guided Tour vs. Self-Guided
The big decision you need to make before walking the Freedom Trail is to take a guided tour or self-guide your visit. There are advantages to both options.
Guided Tours
I love guided walking tours! Guides can really bring a place to life, especially when there’s a modern city like Boston covering the historical landscape. I went with Hub Town Tours. They offer small group tours covering all the sites on the Freedom Trail. Our guide did an amazing job telling the story of the Sons of Liberty and pointing out historical bits hiding in plain sight. Highly recommended.
The downsides of a guided tour are basically: 1) it costs money and 2) you can’t explore at your own pace. To me, an expert guide is well worth the investment. I made up for the pacing by going back to a few select sites where I wanted more time.
Besides Hubtown Tours, you can also check out the official tours by the National Park Service and the Freedom Trail Foundation.
Self-Guided Visit
If you’re more interested in exploring the Freedom Trail on your own, my recommendation is to use the free audio tour from the National Park Service. It’s very well put together, if a bit brief in places. You can download the whole tour for free via the official NPS app (Apple, Google). It even includes a GPS map to keep you on track.
You could also read about each site on the Freedom Trail Foundation website. It gives similar information and links to the websites for the individual sites.
What I would not recommend is winging it. There aren’t many signs along the Freedom Trail, so you need a guide of some kind. Otherwise you may end up staring at a random Chipotle trying to figure out what’s going on.
Highlights of Boston’s Freedom Trail
There are 16 sites in total on the Freedom Trail, but here are 8 highlights where I would plan to spend a little extra time.
Boston Common
Boston Common is basically Boston’s version of Central Park in NYC. It’s considered America’s oldest public park, establish in 1634 by Puritan settlers. In those days it was the “common” pasture for grazing livestock. When British forces were stationed in Boston during the 1770s, they used it as a training ground. Nowadays there’s not much see from those eras, but it’s still a beautiful place to stroll.
Granary Burying Ground
Granary Burying Ground is a historic cemetery where several of the Sons of Liberty are buried, along with other important figures. You’ll find the graves of John Hancock, Samuel Adams, and Paul Revere to name a few. There’s also the grave of Crispus Attucks, an African-American sailor who was the first victim of the Boston Massacre. (More on that event below).
Even if the historical names don’t wow you, it’s cool to see such an old cemetery with all the distinctive skull-and-crossbones graves.
Old Corner Bookstore
The Old Corner Bookstore was originally built as an apothecary shop but became a bookstore during the early 1800s. In 1832, the publishing company Ticknor and Fields moved in. They went on to publish works of such authors as Ralph Waldo Emerson, Henry Wadsworth Longfellow, Harriet Beecher Stowe, and Nathaniel Hawthorne. Today however, the historic brick building is home to a Chipotle. Anyone want a burrito bowl?
Old South Meeting House
Situated on the same busy intersection as the bookstore, Old South Meeting House is where the Boston Tea Party kicked off. Back in December 1773, Samuel Adams called a mass meeting there and organized a protest against British taxes on tea. Old South was the largest public space in town at the time. Thousands of residents gathered there, marched down to three tea ships, and threw 342 chests of tea into Boston harbor. Take that, you rich tea drinkers!
Admission to the church is $15.00 and also includes entry into the nearby Old State House.
Boston Massacre Site/Old State House
OK technically this is two sites, but they go together. In 1770, the road in front of the Old State House (then the Customs House) was the scene of the Boston Massacre. Accounts of what happened vary wildly, but somehow an angry mob of civilians ended up quarreling with British soldiers. Things escalated, and shots were fired into the crowd. In the aftermath, five men lay dead.
This incident went viral, thanks in part to an engraving created by Paul Revere. It was a moment when public sentiment toward the occupying British soldiers turned very negative.
The Boston Massacre site itself is marked by a plaque on the sidewalk. The Old State House is home to a museum that shows what it looked like when the British Royal Governor occupied the building. Admission is $15.00 and includes the Old South Meeting House too.
Paul Revere’s House
The Paul Revere House is the oldest home in Boston. Built in 1680, Paul Revere purchased the property in 1770. At the time, Revere was a prosperous silversmith and engraver. He also became a courier for the Sons of Liberty. After the whole tea incident heated up tensions with the British, Revere was on standby to deliver any important messages (oooh foreshadowing…).
The house is meticulously decorated to look as it would have in Revere’s time. There are some artifacts too, including some of Revere’s silversmith works. It’s well worth the $6.00 cost of admission.
Old North Church
Old North Church is the place immortalized in Longfellow’s poem “Paul Revere’s Ride.” By this time in 1775, tensions with British troops were sky high and the patriots had started amassing weapons in nearby Lexington and Concord. They set up a warning signal in case the British army decided to go after them.
Though the poem is very much the Hollywood version of the story, it’s true that two lanterns were hung high in the steeple of Old North Church as a signal to alert patriots across the Charles River. “One if by land, two if by sea,” and Paul Revere was off to deliver the message that the British were coming.
Besides the famous Midnight Ride, Old North Church gives you a look into the daily lives of colonial Bostonians via an excellent audio guide. A $10.00 combo ticket includes the audio guide and admission to the crypt. Basic admission is $5.00. You can also book a tour of the bell tower, but make sure to reserve in advance. The church is closed seasonally January and February.
USS Constitution
The USS Constitution is the oldest commissioned naval vessel still afloat. She was launched in 1797, when a young United States of America first established the US Navy. Back in those days, the Constitution defended US merchant shipping and traded cannon fire with British ships during the War of 1812. Today, the Navy maintains the USS Constitution as a museum ship.
It’s free to visit the ship and the small museum at the Charlestown Navy Yard. The sailors aboard Constitution are available to answer any questions. If you’d like to learn even more, check out the kid-friendly USS Constitution Museum next door. Suggested admission price is $10-15.
Tips for Visiting Boston’s Freedom Trail
Subway
The best way to walk the Freedom Trail is…um, walking. But it’s worth using Boston’s subway system to save time or reach other areas. It’s called the “T,” and you’ll find both the Orange Line and Green Line are particularly useful. I’d recommend using Google Maps to figure out which is best.
You can pay for the T by using any contactless payment card or buying a pass from one of the machines. Each ride is $2.40. If you’re planning on riding a bunch, pick up a 24 hour pass. It’s $11.00 for unlimited use of the subway, buses, and more.
Ye Olde Taverns
If you need a drink or a bite to eat on the Freedom Trail, there’s a row of taverns fit for the occasion. None of them truly date from colonial times, but the historical vibes are there on Union Street.
- Union Oyster House – Open since 1826, the Union Oyster House is the oldest continuously operating restaurant in America. The building is even older, constructed in the mid-1700s before the America Revolution.
- Green Dragon Tavern – The original Green Dragon Tavern was a favorite of Paul Revere’s and a meeting spot for the Sons of Liberty. The new Green Dragon Tavern is a tribute to the original and features a delicious house beer brewed by Sam Adams Brewery.
- Bell in Hand Tavern – The Bell in Hand claims to be America’s oldest bar, established in 1795. The location has changed a few times over the years, but the name stuck. Beware the weekend party crowds if loud music isn’t your thing.
Ye Olde Ghost Tours
Do you want a Freedom Trail experience that’s a bit spookier? Boston is home to a thriving ghost tour scene. To be honest, I was a bit baffled by so many different options.
I ended up going with the Ghosts and Gravestones Tour. It’s a bit pricier than others, but they actually have permission to take guests through the graveyards at night. Our darkly comedic guide brought an infectious enthusiasm to his retelling of Boston’s many ghost stories. And using a trolley-style minibus kept the walking to a reasonable amount. Check out their tours if you’re looking for a fun evening activity!
