Boston’s Freedom Trail

What better way to explore a town you are visiting than by walking around?  Well, if you happen to find yourself in the northeast, you are in for a treat.  Boston’s Freedom Trail, a 2.5 mile path, takes you along 16 different historical sites, past countless museums, and other cultural sites.  If you are looking for a city wide tour, I recommend picking up a ticket for a hop-on and hop-off bus, but I find that walking or running the streets gives you a more in-depth look at it all.

A few weeks ago, my friend Lindsay and I happened to be traveling to the Beantown and of course on the day we had planned to walk the Freedom Trail, it was raining cats and dogs.  After finishing brunch and wandering a few stores, the rain started to ease up.  We decided to check out Boston Commons in hopes that the sun would shine through.  Slowly but surely we found ourselves at the start of the trail and the rest is history.  Really though…


The tour itself (self-guided or guided) starts at the visitor center in Boston Commons and travels along a noticeable brick path. Here you can pick up pamphlets, maps, and other guides of things to do in the city.  You can even take a tour by a guide dressed in historically themed garb if you are so inclined.

 Note: there is another visitor center at Faneuil Hall where you can select a tour.


Stop #1
Beacon Hill – Black Heritage Trail – Otis House Museum


King’s Chapel – Historic Burying Grounds – Park Street Church


 The idea for the trail was created by a local  journalist William Schofield back in the 1950s.  When it was finally created in 1953, almost 40,000 started walking the trail each year.

IMG_6230Because in our society, placing a popular chain steak house within a historic monument (or area) is totally normal.  Just dining alongside Paul Revere’s grave – no big deal.  Here you pass along the Old South Meeting House and Old State House before arriving at Faneuil Hall.


Faneuil Hall – a marketplace and meeting spot that has been around since 1742.  It has even been the spot for many famous speeches by Samuel Adams, James Otis, and others that supported independence from Great Britain.


Quincy Market – a tour in itself.  This place is stacked with eateries and I guess you could call it Boston’s food court.  There are some classics such as chowder (shall I say “chowda”?) and lobster rolls, as well as good ‘ol ice cream and pizza.  This could certainly serve as a nice lunch spot and on a nice afternoon, there are plenty of places to sit outside and soak up the sun.  The ground was still a bit damp and the air a bit chilly, so we weren’t as lucky, but still lots of fun to people watch.

The path winds in and around the North End, where you will soon find yourself in the Italian district and if you are still hungry, I highly recommend picking up a cannoli from the well-known Mike’s Pastry shop.  We saw person after person heading back towards the center of town with a white box that read Mike’s Pastry and knew we had to give it a shot.

IMG_6238Don’t be alarmed by the length of the line.  They know how to turn customers over and make those customers happy – or at least their stomachs happy.  

IMG_6246Hungry enough to fill an entire box?  How about some to take home?  Nope, we decided to eat ours then and there.  Plus as a couple of gals from California, we were trying to be green and reduce waste 😉


I selected the double chocolate flavor while Lindsay went with cookies and cream.  Hands down – best cannoli ever.  I’m just salivating as I think about the sweet ricotta and crunchy pastry dough.   Sweet tooth satisfied and it’s time to continue along the trail.

IMG_6252Old North Church past the grand ‘ol Paul Revere statue and the Revere household


As you continue along the Charlestown Bridge, check out all view over the Inner Harbor

IMG_6255 Sun starting to set over the Zakim/Bunker Hill Bridge

IMG_6256 IMG_6258

The most adorable houses leading up to Monument Square and Bunker Hill, which means you have made it to the end!

Bunker Hill was the first mega-conflict between the British and Patriot forces during the American Revolutionary War.


As we headed back on the trail towards the North End, we stopped by the USS Constitution.  The ship was closed for a private event, but we were still able to watch the nightly ceremony where guns are fired off of the ship at dusk.  If you happen to be in the area and don’t mind waiting outside the gates, it is one beautiful way to watch the sunset.


The Freedom Trail
~ Sites ~ Map ~ Tour ~

“The traveler sees what he sees.  The tourist sees what he has come to see.” G.K. Chesterson


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