Freedom Trail: Exploring Boston’s Revolutionary History on the Cheap


Just follow the brick path as demonstrated by Amanda

Why you need to check it out 

Boston’s Freedom Trail is probably the most obvious tourist attraction when visiting Boston. And for good reason… it’s the best way to see some of the most significant historical sites the city has to offer!  For those who are new to Boston, the Freedom Trail is a 2.5 mile walking trail that guides you through Boston’s rich history one historical site at a time. And the best part is there is literally a little brick path to follow the whole way so you can’t get lost! This is a big bonus for me considering I get lost a lot, just ask Amanda.

There are a lot of reasons to take this trek the Freedom Trail. First, the majority of the historical sites along the route are free or operated on suggested donations which is always a plus in my book. A lot of the suggested donations are small and even though they are not required just donating at all is greatly appreciated. Second, there are three very old cemeteries, three equally old and beautiful churches, museums galore, and countless photo ops.

Starting Out

The best place to start this tour is in the Boston Commons. If you’re taking the T in the Park Street stop is right in the middle of Boston Commons (Red and Green lines). Downtown Crossing is an easy stop to get off at too if you’re coming in on the Orange Line and don’t want to switch trains, its literally two blocks away. (Orange and Red lines).

Headstones in Copp’s Hill Burying Ground

Boston Commons is a big park right in the middle of downtown. There’s tons of outside space for enjoying some sunshine, riding the swan boats (in summer) and skating on Frog Pond (in winter). On the Northeast corner of the park is the State House, a massive brick building with a gold colored dome on top overlooking the commons. Around the corner on the East side of the commons are the Park Street Church and Granary Burying Ground. If you’re like me and have an infatuation with old cemeteries then you’ll love this one. Lots of weathered head stones with skulls and crossbones engraved at the top and, fun fact, Sam Adams, John Hancock and Paul Revere are buried here!

Private church cubicle

Just down the street you’ll come across Kings Chapel and Burying Ground for your second church and cemetery on this trail. Be sure to stop inside the church. It does not cost anything to look inside but the suggested donation is $2 per person. Immediately after

Inside King’s Chapel

walking in Amanda got a “weird feeling” and couldn’t wait to get out of there. It was definitely a little bit eerie but I thought it was pretty neat. They had private enclosed booths instead of pews for individual families to attend mass in. Very different from anything else I’ve seen. Photographs are allowed just make sure you turn the flash off, this goes for the other churches and indoor exhibits as well.

On your way to the Old South Meeting House you’ll pass the Ben Franklin Statue and the Old Corner Bookstore.  The meeting house is the first public building in Boston and right out front is the site of the Boston Massacre. The entrance to the Meeting House brings you through the gift shop where you can buy some souvenirs for your people back home, if they’re lucky,  and check out the museum. There is a fee to enter the museum, adults are $6. For more information on entrance fees and events visit

Juxtaposition of old and new at Faneuil Hall

Just across the plaza is Faneuil Hall and Quincy Market. If you need a break from all of this glorious history you’ve been soaking up then take some time  to wander around Quincy Markets pedestrian cobblestone main drag. Save you’re hunger for a little farther down the road as the North End Portion of the trail provides the best food options. 

Take a Break

Continuing along the path just past Faneuil Hall you’ll walk a short stretch on Union Street. The whole street is lined with pubs and the famous Union Oyster House. If you need to wet your whistle stop by America’s oldest tavern, Bell in Hand (1795), for a Sam Adams Brick Red (served exclusively in Boston).


The original Pizzeria Regina

Once you cross over into the North End you’ll be overwhelmed with the smell of amazing Italian food so if you’re hungry this is a good place to fuel up. My favorite place to stop and eat is the original Pizzeria Regina opened in 1926. This is a Boston favorite and well worth the stop. Be prepared for a line especially if you’re visiting in the summer or on a weekend. Back on the little brick path you’ll find the Pierce-Highborn House, one of Boston’s oldest buildings and the Paul Revere House. For hours and prices visit

Old North Church

Continuing through the North End you’ll come across the Paul Revere statue at the entrance to an incredible brick courtyard before entering the Old North Church. Here there is no entrance fee but a suggested donation instead. At the top of the hill you’ll stumble upon your third and final cemetery on this tour, the Copp’s Hill Burying Ground. This is by far the prettiest of the three sitting on top of the hill looking over the church down the street and the harbor off in the distance.


USS Constitution getting some work done in the dry dock

Saving the Best for Last

For the last part of the trail you’ll cross the Charlestown bridge into, who would’ve guessed, Charlestown. This is by far my favorite part of the trail first stopping at the USS Constitution and last the Bunker Hill Monument. The Constitution Museum and ship operate on a suggested donation. If you want to climb aboard the Constitution make sure you bring government issued ID as you have to go through a security check point run by the U.S Navy. Visit to find out more details about suggested donations. When it comes to the Bunker Hill Monument you can climb to the top of the 294 step Monument without cost. First stop across the street at the museum for a quick history lesson and you’re entrance ticket. It’s free to climb and in the off season you don’t need to stop at the museum to pick up a ticket.

Bunker Hill Monument

Boston’s Freedom Trail really is an incredible way to see such a historic city. If you loved this walking trail Boston has a number of self guided walking tours including the Boston Harbor Walk, Black Heritage Trail, Irish Heritage Trail, Boston Women’s Heritage Trail, and the Walk to the Sea Trail.