Home ยป The Freedom Trail in Boston: Everything You Need to Know From a Local

The Freedom Trail in Boston: Everything You Need to Know From a Local

Hi everyone and happy September! It’s currently Labor Day weekend and I spent today exploring my home city, Boston, with my dad! I’ve lived outside of Boston my entire life and have walked along the famous red bricks aka the Freedom Trail, countless times, but have never actually walked the entire trail start to finish. Today I was determined to do that. Whether you’re a Boston local or not, I recommend everyone walks the Freedom Trail at least once! If you do decide to walk the Freedom Trail, here’s everything you need to know from a local!

Before You Begin…

Before we begin, here are some basic Freedom Trail facts. First, what is the Freedom Trail? The Freedom Trail is a 2.5 mile long (it’s actually more like 3.5 miles) path through downtown Boston, Massachusetts that passes by 16 significant Revolutionary War sites. It’s marked by a winding red brick path that passes through downtown Boston, the North End, and Charlestown. The trail begins at the Visitor’s Center on the Boston Common and ends at Bunker Hill Monument in Charlestown.

I recommend beginning at the Boston Common Visitor’s Center, located at 139 Tremont St, Boston, MA 02111. Here you can purchase a map and begin the official trail. And no, maps aren’t free. This building is also where most tours begin, including my BRAND NEW Airbnb tour!

As an Airbnb Experience host, I’ll be bringing groups on a walking tour along the Freedom Trail! The tour is about 3.5 hours long and covers 3 miles. We will begin at the Boston Common Visitors Center and end near the Old North Church. If you’re interested in booking my Freedom Trail History & Photo Tour, you can find more information here.

Here’s our route:

Freedom Trail Stops #1 & #2: Boston Common & State House

From the Visitor’s Center make your way through historic Boston Common, America’s oldest public park, to the Massachusetts State House. This has been the seat of the Massachusetts government since its opening in 1798.

Freedom Trail Stop #3: Park Street Church

The next stop in Park Street Church, which sits at the corner of Tremont and Park streets. This church was founded in 1809 and was originally the site of Boston’s public grain storage, or granary. This leads us to the next stop, the Granary Burying Ground.

Freedom Trail Stop #4: Granary Burying Ground

This burying ground was established in 1660 and houses some of America’s most notable revolutionists, including Paul Revere, Sam Adams, and John Hancock.

Freedom Trail Stop #5: King’s Chapel & Burying Ground

Across the street is King’s Chapel and its burying ground, Boston’s first Anglican church. This burying ground is the oldest English one in the city. It is full of graves from Mayflower voyagers, including the first woman who was believed to step off the ship.

Freedom Trail Stop #6: Boston Latin School & Benjamin Franklin Statue

Next, walk down School Street to the site of the old Boston Latin School, the first public school in the US! This school offered free education to boys, and is well-known for having Benjamin Franklin, John Hancock, and Samuel Adams as students. The Benjamin Franklin statue and Old City Hall can be found here.

Freedom Trail Stop #7: Old Corner Bookstore

Further down this road you’ll hit the Old Corner Bookstore. It’s now a Chipotle.

Freedom Trail Stop #8: Old South Meeting House

Across the street you’ll find the Old South Meeting House. Once a church, the tea tax debates occurred here in 1700s. This building gained fame as the organizing point for the Boston Tea Party on December 16, 1773.

Freedom Trail Stops #9 & #10: Old State House & Boston Massacre

From here, walk down Washington Street to the Old State House! This site is famous for two main reasons. First, this building is the oldest surviving public building in Boston. It’s also where the Declaration of Independence was first read off the balcony. Second, this is the site of the Boston Massacre, which occurred on March 5, 1770. Five Bostonians lost their lives as they fought against the British Redcoats.

Freedom Trail Stop #11: Faneuil Hall

Next up is Faneuil Hall! Walk down Congress Street until you hit this historic, tourist hotspot. The actual Faneuil Hall once hosted America’s first Town Meeting and is known for being the “Home of Free Speech”. Today, Faneuil Hall Marketplace comprises of the building itself, Quincy Market, North Market, and South Market. These buildings are full of restaurants and shops. I recommend strolling through Quincy Market and eating at one of the many food stands located here!

Continue along the red brick path as you make your way into the North End! I was most excited for this portion of the Freedom Trail since it covers the North End and Charlestown, two of the lesser explored areas for me. As a local, I’m in downtown Boston often, but never really these places. Faneuil Hall marks about halfway along the trail (about 1.5 miles done). There are less sites in the second half and they’re more spread out.

Let’s do the last mile or so, shall we!

Once you arrive in the North End you’ll walk down Hanover Street. This is the hub of the neighborhood and where you’ll find the best Italian restaurants and bakeries. My personal favorite is Mike’s Pastry. If you like cannolis, grab one here!

Freedom Trail Stop #12: Paul Revere House

You’ll want to turn onto Richmond Street to see the Paul Revere House at North Square. As the name suggests, this home was owned by Revere from 1770-1800 and is the oldest remaining structure in downtown Boston! You can pay to enter the home and museum if you wish.

Freedom Trail Stop #13: Old North Church

Further down Hanover Street you’ll hit the Paul Revere Mall and Statue. This was my first time here and I enjoyed walking around! At the end of the Mall is the Old North Church. Built in 1732, this is Boston’s oldest church! This is also the site that launched Boston into the Revolutionary War. It’s in this bell tower that lanterns signaled that the British were coming, marking the start of Paul Revere’s march to Lexington/Concord for the battle.

Freedom Trail Stop #14: Copp’s Hill Burying Ground

The last stop in the North End is Copp’s Hill Burying Ground. From here, you’ll walk over the North Washington Street Bridge into Charlestown! The Freedom Trail splits here in two directions, forming a loop, so you can choose whether you’d like to see Bunker Hill Monument or the USS Constitution first. We did Bunker Hil.

Freedom Trail Stop #15: Bunker Hill Monument

Bunker Hill is one, a scenic hilltop in Charlestown providing view of the Boston skyline, and the site of the Bunker Hill Monument. This monument commemorates the Battle of Bunker Hill which occurred on June 15, 1775. This was the first major battle of the Revolutionary War.

Freedom Trail Stop #16: USS Constitution

From Bunker Hill we walked a short ways to the Charlestown Naval Yard where we saw the USS Constitution. This ship is the oldest commissioned warship afloat in the WORLD! Pretty cool. There is also a museum here, and you can walk onboard the ship!

This marks the end of the Freedom Trail! The brick walkway claims to be 2.5 miles, but I ended up walking over 4 miles. Either way, this is a GREAT way to see the city of Boston and to learn a lot about the Revolutionary War in a short period of time. I didn’t actually go inside any buildings- to do this, you’ll have to pay, so the entire trail took me about 2.5 hours. If I visited some of the buildings, it would probably take 4 hours.

Pro-tip: Thirsty? Head to the Anchor Bar for a drink to celebrate the end of the Freedom Trail! This outdoor bar is super trendy (they have swings and bean bag chairs trendy) and the best frose!

Want more New England content? Check out my Ultimate New England Bucket List!!

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