Why You Need to Walk the Freedom Trail in Boston

Why You Need to Walk the Freedom Trail in Boston

The noted writer and philosopher George Santayana is attributed the quote “Those who cannot remember the past are condemned to repeat it.” As a passionate student of history since my high school days, I’ve come to fully appreciate this quote and do my best to not only learn about world history, but the history of where I live and the country I call my own. After dedicating years of my life to studying the Holocaust, I was finally able to make it to Poland and tour both the Auschwitz and Auschwitz II – Birkenau Concentration Camps. I walked along the Berlin wall. I visited Washington, DC. I remember the conflicts, what happened, why such events took place. I contemplated what they meant to me, but more importantly, what I was going to do with those thoughts and emotions. When I was in Boston, I made sure to walk the Freedom Trail.

The Freedom Trail is a 2.5 mile-long path that winds through Boston, passing 16 historically significant sites. The official website is loaded with more information to help you plan your tour, maps, FAQs, locations, basically everything you could ever want to know about how to walk the Freedom Trail.

If you choose to walk the Freedom Trail on your own, at your own pace, all you have to do is follow the inlaid brick pathway…and don’t forget to look up!

I chose to join a guided tour by the best character-tour-guide I could have ever imagined. Shrug off whatever feelings of apprehension, embarrassment, or uneasiness…taking a guided tour as you walk the Freedom Trail is the best way to absorb the most history you possibly can. Not only are their tour guides knowledgable about Boston’s history, but how the city’s history still affects us today.

Why You Need to Walk the Freedom Trail in Boston
Our guide, “Elizabeth Oliver,” kept us informed and entertained throughout the 90 minute tour, constantly joking about her costume!

The tours are offered daily, and usually start at the Information Center at the Boston Commons. You honestly couldn’t miss it if you tried: tons of tourists milling about, wonderfully loud tour guides pique your ears, and if that’s not enough…just look on the ground and find the actual trail. It’s there, I promise. So without further ado, here are my 5 reasons why you should walk the Freedom Trail in Boston!


Why You Need to Walk the Freedom Trail in Boston

Reason #1: Connect

I’m all about visiting beautiful locations: desert landscapes leave me in awe, sandy beaches soothe my soul, and downtown chaos ironically gives me peace.

But after a while, I find myself needing a change. Something deeper. Some way to connect to a location.

For example: a few years ago, I took a trip to San Francisco for a solo getaway weekend. While I was there, I visited Angel Island with some family members that I ran into.

Visiting an island in San Francisco Bay seemed like a fun day trip, but I was more excited about spending time with my family members than the actual island. I’d already visited another island located in San Francisco Bay – Alcatraz – numerous times.

What I wasn’t counting on was learning so much about the immigrants that came to America, not through Ellis Island, but Angel Island. What? Did you know that approximately 175,000 Chinese immigrants passed through Angel Island between 1910 and 1940?

Let me tell ya – learning more about the immigration history that Angel Island experienced gave me an emotional tie to the Island. My curiosity was reignited and I eagerly devoured every fact nugget I could.

Boston has the tendency to fall into the same trap that Angel Island did for me. Sure, it’s a bigger metropolis, full of culture, sports, entertainment, and a budding food mecca…but can’t the same be said of Salt Lake City? Or Minneapolis? Or Tampa?

Boston’s history sets it apart from every other city on the earth. If you choose to walk the Freedom Trail (and I think you should), you instantly gain an emotional connection to the city, especially if you are an American. You see the birthplace of revolution. The spark that ignited the spirit of independence. Yes, it’s that big of a deal. No, I’m not crying. You’re crying.

Why You Need to Walk the Freedom Trail in Boston

Reason #2: Explore

I arrived in Boston with a vague idea of what I wanted to see. Prior to my arrival, I purchased one of those city passes that paid for museum fees and my whale-watching cruise…but aside from those few things, Boston was a blank canvas that I was ready to make my mark on. By taking the time to walk the Freedom Trail, I found myself in neighborhoods I didn’t even know existed!

After the guided tour concluded at Faneuil Hall, I followed the red brick road that winds around Boston towards the Paul Revere House. As I neared closer to the actual House, I became acutely aware that the street composition had changed. Instead of black asphalt, it was cobblestoned. I looked up and realized that I was in the North End, a neighborhood that wasn’t initially on my radar.

Why You Need to Walk the Freedom Trail in Boston

Reason #3: Learn

I believe that when we leave this earth, the only thing we can take with us is the knowledge we’ve gained during our lives. So if this is the case, why not learn as much as we possibly can?

I have a roommate that is just full of useless facts that would land her on recurring episodes of Jeopardy. I’m constantly amazed at the wealth of information that she’s able to recall at the slightest hint of curiosity. After walking the Freedom Trail, I was able to drop a few knowledge bombs on her as well.

Did you know that John Hancock (yes, THE John Hancock of the Declaration of Independence fame) earned his money “the old-fashioned way?” When our guide asked the group how he earned his money, people yelled out the standard answers – trade, bootlegging (seriously?), black market (yeah, there were some real winners in my group).

Finally after the morons subsided, I chimed in with the correct answer:

“He inherited it.”

Oh, yeah. Score to the single girl in hot pink pants.

Why You Need to Walk the Freedom Trail in Boston
Granary Burial Ground where John Hancock, Paul Revere, and other prominent revolutionaries are buried, including all 5 victims of the Boston Massacre.

Reason #4: Uniqueness

Whenever I travel to new places, I like to experience something unique to that area and something that I don’t experience on the regular.

When in Germany, I visited beer gardens.

When in Copenhagen, I took a canal cruise.

When in Hawaii, I snorkeled.

The New England area was the center for the American Revolution and I would be remiss to ignore the activities, historical and cultural impact that it has had on my life as an American.

What better way to learn more about what makes America tick than to dive right into the history of its birth?


Reason #5: Fun

I can’t rightfully finish this post without talking about how fun walking the Freedom Trail was. My tour guide was absolutely hilarious and full of knowledge, which is what you’d hope to experience. She helped bring the history of the city to life, in a way that will stay with me forever.


Take my word for it – walk the Freedom Trail and embark on a journey that will ignite the Spirit of freedom within you!

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Why You Need to Walk the Freedom Trail in Boston