The juxtaposition of history’s battle against the perpetual forward push of time could not have been more apparent than in Boston. As I traveled along the Freedom Trail, there seemed a constant clash between the two. For every place saved from the ravages of modernization, two seem to have been lost. Historic sites, many key to our nation’s birth, were surrounded by modern buildings. In every place time simultaneously stood still and raced ahead, eager to be remembered yet perpetually forgotten. These sites are treasures, links to our birth and past, but so far outside our everyday consciousness. The Freedom Trail serves as an apt reminder that we can not afford to forget our past. We can not forget what these places mean to who we are. It seems the message found on the Freedom Trail is one relevant even today, if only we are willing to listen to it.
The First Steps
In all likelihood before you reach the proper beginning of the Freedom Trail, you’ll have taken a stroll through history. The Boston Common serves as a gathering place for all of Boston. This beautifully open space invites you into the city and offers itself up for any time you have to give it. I encourage you to take a few moments to wander, especially through the gardens. When you’re ready to walk to trail, head on down to the visitors center on the green. The center here will provide you with a map (for a small fee) but unless you’re wanting a guided tour you can leave after that.

The trail will lead you through some of the common to the Massachusetts State House. This fantastically beautiful building is one of the oldest state houses still in use. Constructed in the 1790s, it remains a wonderfully place to start your tour into the history of our nation and Boston. We didn’t get an opportunity to tour the state house because it was closed on the day we visited, but I still think it is a must do on your trip.
The next stop along the trail was the last stop for many of our most iconic revolutionary figures. It’s also a place which will illustrate the massive clash between exploring our history and being respectful of it as well. The Granary Burial Ground is one of the oldest in Boston. It is the final resting place of revolutionary giants like Sam Adams, Paul Revere and John Hancock. Yet, even these men are “recent” additions to the ground. As you walk among the headstones, you can see how time and weather will wear down all things. What struck me the most wasn’t the age of the graveyard but the encroachment of our modern world.
The Granary Burial Ground is surrounded by tall buildings, built directly to the edges of the cemetery. They have encroached so far that plaques are attached to the buildings because the headstones were destroyed in the process. It was simply a striking realization that the push towards the future couldn’t be stopped to respect the dead.
To add to the striking dichotomy of past vs present, were the tour groups. I understand that this is an “attraction” along the freedom trail, but seeing tour guides leading groups of 15-20 people through the ground was strange. It made me really wonder if even I should be there walking among those graves. Was the exploration of my small group of two any better than that of the large group? I still don’t have an answer for that, but we all need to look for that answer in ourselves. This moment and place stuck with me for the rest of our trip and is still with me now.
The Heart of the Freedom Trail
Beyond the opening steps of the Freedom Trail, you dive deeper into Downtown. This winding stretch has a number of great sites. These sites will come in fairly rapid succession and are the easiest to walk between.

Shortly after the Granary Burying Ground sits King’s Chapel. One of the oldest congregations in the city of Boston, the Chapel still holds regular services. I was particularly fascinated by the closed pews and the history behind the owners, which the church did a wonderful job of presenting.
Past the Chapel lies the Old City Hall and the Old Corner Bookstore (which is unfortunately, unless you’re hungry, a Chipotle now). We passed by these to visit one of the more storied sites on the trail. The Old South Meeting House served as one of the key places which helped foment the American Revolution. Of these moments, it is perhaps the meeting here just prior to the Boston Tea Party which has given it such a reputation. The inside, which requires paid admission, serves as a wonderful museum which tells a history of Boston. The interior is also gorgeous, so even just stepping inside for that is worth it (especially if you’re using the GoBoston Card).
After you leave the Old South Meeting House, the next stop on the Freedom Trail was one of the more surreal. Just behind the Old State House lies the site of the Boston Massacre. This pivotal moment in American history is memorialized by a simple brick marker on the ground. However, you stand surrounded by the hustle and bustle of a big city. Major streets intersect just steps away and life moves on as it always does. Like much of this trip, it truly helped to put perspective on our place in history.
Shopping Along the Freedom Trail
One might wonder what to do next after standing in a graveyard, centuries old churches, and the site of a massacre. Well, how about some good ole fashioned shopping! Honestly, there is nothing more American than consumerism. Just down the street from the Boston Massacre lies Faneuil Hall Marketplace.

Faneuil Hall proper stands in front of the larger marketplace. The hall itself, with the iconic statue of Sam Adams out front, still serves as a market while also doubling as a museum of sorts as well. Faneuil Hall was one of the first public markets in the city and was also the site of some slave auctions in the city.
Once you’ve passed through the hall, you’ve got the option to walk the Quincy Market (directly behind) or one of the two other marketplaces. These aren’t directly part of the Freedom Trail, but we took the opportunity to take a break. We enjoyed looking at the architecture in Quincy Market and the smells from all the restaurants. Ultimately, walking through the market is a simple diversion from the trail and not a necessary part of the visit.
Walking Through the North End
Faneuil Hall serves as the final stop on the “heart” of the Freedom Trail. Beyond this point the trail is longer between stops. If you’re thirsty, the Bell in Hand Tavern (oldest drinking establishment in Boston) is along this part of the trail. You’ll also cross over the Rose Kennedy Greenway, which hides Interstate 93, in order to enter the North End.
The North End is home to the final two stops on the Downtown Boston side of the Charles River. The first of these is the Paul Revere House. Like many other parts of the trail, his house is squeezed in among more modern surroundings. The house requires admission, which is fine because you love history and you’ve bought the GoBoston Card already.

The itself remains in much the same shape as it was when Revere last lived here. Parts have been restored, but much of the furniture in the home is original since it was passed through the family and donated to the museum. It serves as an intimate look into the life of one of our founding fathers, something that was surprisingly rare on this journey.
The final stop in the North End is one church we didn’t go into. The Paul Revere Mall (not for shopping) was closed for renovations so we didn’t walk through it. The Old North Church is also one of the rare sites that didn’t accept the GoBoston Card, so we choose not to go in. You can walk the outer grounds and I found that after a long day (with a long walk back) that it was ok to skip.
Across the Charles River
We did not walk the entire trail in a single day. It leads across the Charles River and this adds significant length to any return journey by foot. We returned to the trail on the final day of the trip, shrouded in a perpetual mist.

There are two locations across the Charles River which deserve your attention. The first is the absolutely wonderful Charlestown Navy Yard and its prized pupil, the USS Constitution. This was my favorite location on the entire trail.
The USS Constitution and visitor center are superbly educational. I encourage you to take your time in the visitor center, especially because you’ll have all the time you want on the Constitution as well. It is well worth the time spent learning about the Constitution and sailing in general.
Once you’re on the Constitution, don’t be afraid to ask questions. The sailors stationed on the ship are all active duty and most are more than happy to answer any questions you have to the best of their ability. Though much of the ship itself is restored or not original, she is absolutely gorgeous. I likely could have spent even more time here, but you’ve got to move on eventually.

The final stop is the Bunker Hill Monument. The monument and its surrounding grounds offer a unique view of the city below. While the famous battle borrows its name from Bunker Hill, the actual site of the fighting and even the monument itself is on Breed’s Hill. Those not afraid of heights can climb the 294 steps to the top, but I choose to stay at the bottom. You should also visit the Bunker Hill Museum at the bottom of the hill and across the street from the monument.
Closing Thoughts
The Freedom Trail is a journey through history. It’s a juxtaposition between our remembrance of the past and the journey to the future. While I’ve grown up my whole life near the oldest city in America, it never felt anything like Boston did. I’d chalk that up to the constant immersion in my local history, something I’m sure many Bostonians would understand.
If you’ve only got a day in Boston, the Freedom Trail would be a mighty full day. Ultimately, I much enjoyed having split it into two days with a mind that three might have been best. There is so much to see in Downtown Boston that you can mix in with walking the trail. I’m happy that I was finally able to visit so many places with a deep historical meaning to my country.
If you’d like to read more about how I planned my entire Boston trip, check out my blog Preparing for One Week in Boston. Thanks for reading and don’t forget to follow me on Instagram or Facebook to journey along with me live! If you loved this post, then pin it and check me out on Pinterest as well!
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