Contex Travel NYC

Context Travel NYC: Uncovering Hamilton and Revolutionary New York Tour

When it comes to the Revolutionary period, New York City has a fascinating history. 

However, NYC hasn’t done as great a job as Boston or Philadelphia in showcasing this to the public. When you walk through the streets of Lower Manhattan, signs of Colonial and Revolutionary times aren’t prominently displayed.

That doesn’t mean New York’s past is gone or that it can’t be found as you walk from street to street. On the contrary, you just have to know where to look. That’s where a Hamilton walking tour in NYC comes in!

Context Travel NYC - Uncovering Hamilton & Revolutionary New York
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Context Travel NYC:
Uncovering Hamilton and Revolutionary New York Tour

Let me go out on a limb here and ask what comes to mind when I say, Alexander Hamilton.

Now, if you’re like most people planning a New York City trip, you undoubtedly think of the hit Broadway musical. You know the one, who’s tickets are harder to come by than a rainbow with a pot of gold!

But, Hamilton fans and history buffs, alike, have become curious about Alexander Hamilton’s life and story. They’ve come to New York by the busload. What they want is to see and hear the real-life places and stories behind the man and the musical.

They’ve come in search of the Founding Fathers and revolutionary war sites in New York.

As a (nerdy 😉 ) teacher, I love it when people are inspired to go deeper and learn more, particularly when it involves closing the books and hitting the pavement.

For this reason, I was thrilled to join a Context Travel NYC tour called Young, Scrappy, and Hungry: Hamilton and Revolutionary New York. Our small group of 5 people (Context tours never have more than 6.) met in downtown NYC on a bright, Saturday morning.

Our Hamilton Tour NYC was led by one of Context Travels passionate scholars, an expert in New York Revolutionary War history studying for his Ph.D.

We started where early colonial life began in New York, which was then called New Amsterdam.

Most people, Americans included, don’t realize New York was not first settled by the English. Rather, it was the Dutch who, later on, were forced by the British to surrender their colony.

Contex Travel NYC
A marker in Battery Park showing the former location of Fort Amsterdam.

As the tour began, we stopped in Bowling Green, New York City’s oldest park.

We listened as our Context Travel Tour docent set the scene with the signing of the Declaration of Independence. When the news finally reached New York a couple of days later, we heard how the King George III statue and other royal symbols in the park were disposed of by American Patriots known as the Sons of Liberty.

Unlike visiting Bowling Green with just a guidebook or a Wikipedia blurb, our group had an expert who knew exactly where to direct our attention. He showed us still visible signs of the damage left behind by the Sons of Liberty.

When you can actually touch history, the scene springs to life before you.

It was also at this early point when I realized Context Travel Tours were not really, tours. Context walking tours are like thematic, experiential field trips. (Who doesn’t love a field trip!?) This was going to be a walking Revolutionary period history lesson, and it was so exciting to see what we would discover next.

Contex Travel NYC

We walked, talked, and asked questions through Battery Park and into Castle Clinton. While others hurriedly moved past to board boats for the Statue of Liberty or were searching their maps for things to do in NYC, we talked about Alexander Hamilton arriving as an immigrant to New York to pursue his education.

We looked out over New York Harbor and discussed its strategic positioning for both the British and the Patriots leading up to and during the Revolutionary War.

Contex Travel NYC
The Watson house is one of NYC’s last Federalist style buildings built in 1800 and now surrounded by skyscrapers.

Our group continued by weaving its way into the oldest section of New York. On the way, we passed by the Watson House, former home to James Watson and a Federalist along with Hamilton.

Lower Manhattan doesn’t have the grid street pattern as in midtown and upper Manhattan. Instead, early Dutch settlers built streets based on Native American pathways and the natural landscape of the island.

This is the reason why downtown streets like Stone, Beaver, Pearl, and even Broadway meander and curve. If you’re visiting other neighborhoods in NYC, you’ll notice the same applies to NYC’s Greenwich Village. 

Along the way, our Context Travel docent talked about Hamilton’s role in the Revolutionary War. He joined the militia in 1775 and worked his way up the ranks. Eventually, Hamilton became a senior aid to George Washington.

Contex Travel NYC
Alexander Hamilton

At this point in the conversation, our docent mentioned the name, Hercules Mulligan. Now, I’ve always been a history buff, but I had to admit I didn’t know much about this guy.

Our expert scholar talked in detail about Mulligan’s connections to Hamilton and how he incredibly saved George Washington’s life twice. It’s at moments like these when I can’t help but wonder about all the historical information and stories still to be learned!

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And so, fitting Context Travel’s mold as an “intellectually curious traveler,” I asked a ton of questions.

I never felt as if I was holding up the group or going beyond our group leader’s expertise. Quite the contrary, in fact. My questions were welcomed and prompted others to ask their own questions for a truly in-depth conversation.

The tour continued to Revolutionary period spots like Fraunces Tavern. It was here after the Revolution where George Washington hosted a farewell dinner, thanking each of his closest military aids one-by-one.

Contex Travel NYC

At Federal Hall, George Washington’s Statue looks out over today’s financial district.

Although the original Federal Hall has since been demolished, this was the site of the first congress and where Washington was inaugurated. Hamilton played a key role in helping the Constitution to be ratified and became the first Secretary of the Treasury.

The Federal Reserve Bank of New York, founded by Hamilton, is just a few buildings away.

I couldn’t help but think how I’ve walked by these spots dozens of times without piecing together their Revolutionary history.

A couple of times, I even went against my own NYC dos and don’ts, stopping suddenly on the sidewalk to look without pulling over! 😉

Contex Travel NYC
George Washington’s view where he gave his inaugural speech back in 1789 has changed just a bit…

The sign of a great tour is one that is a walking, interactive, and in-depth discussion. Context Travel accomplished this with ease.

When Context tours come to an end, you have a fuller understanding and the inspiration to go even deeper into the subject.

I was so interested in what I’d learned that I spent the weekend reading more about Hercules Mulligan and deciding which Alexander Hamilton books to read.

Contex Travel NYC

Towards the end of our Context tour, we entered Trinity Church’s cemetery to see the resting places of Alexander Hamilton, his wife, and family. Eliza’s sister, Angelica, and Hercules Mulligan were also buried nearby.

Contex Travel NYC

The cemetery was crowded with a couple of other revolutionary war tours packed with a lot of people in a group. As I squeezed passed one of the groups, I overheard a man asking his wife if she could hear what the guide was saying…

Now, I’m not sure what your reason for traveling is? Maybe you’re looking to check off items on your must-see and do list. Or perhaps, you’re hoping to grow in some way from your experiences?

If you’re like me, you truly believe in the teaching power of travel. But, I get it. Your time as a traveler is precious. So, make certain the experiences you choose are ones that’ll stay with you long after you’re back home.

If you’d like to go deeper on your next trip, check Context Travel to learn about their offerings in 40 cities around the world. Visit Context Travel New York for more information about the tours offered in NYC.

Would you like to take a Hamilton tour in New York City?

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Hamilton Tour NYC- Uncovering the Man and the History Behind the Musical
Disclosure: I was a guest of Context Travel. This teacher, traveler, history nerd genuinely loved learning with Context Travel New York. As always, all opinions are my own. 

20 thoughts on “Context Travel NYC: Uncovering Hamilton and Revolutionary New York Tour”

  1. I have been to New York quite a few times and this is the first time I’m seeing this. Definitely a different and unique tour! I really like getting to know the lesser-known sides of the history of a city/place.

    What I read so far about Context Travel has been very positive. Really interesting and insightful tours.

    1. Jackie Sills-Dellegrazie

      Even as a local, Hugo, this Hamilton NYC tour showed me a different side to many places I walk past all the time. Context tours are really in-depth and personal. I’d recommend them for NYC and any city you plan to visit where they offer a tour. 🙂

  2. Wow, I never knew that New York was first settled by the dutch. It also made me chuckle when I read Hercules Mulligan – Taylor and spy, because it really reminded me of Kingsmen 😀 Great article, keep up the good work

    1. Jackie Sills-Dellegrazie

      Thanks, Tom. 🙂 Yes, most U.S. history books only focus on the English 13 colonies, which is such a shame. The Dutch history of NYC is so rich.

  3. I am nerding out right now! I loved reading this and learning some little nuggets of history! Like Hercules Mulligan. I had no idea! That doesn’t really sound like a name from back then either! Love it. Thanks for sharing. We would totally do this tour if we were headed to New York! Will have to keep it in mind for the future 🙂

    1. Jackie Sills-Dellegrazie

      Thanks for reading, Kate. We can totally nerd out together over Hercules Mulligan! He is such an interesting Revolutionary War figure.

  4. I’m not too big on cemeteries, but honestly it would be so cool to see the grave stones of Alexander Hamilton. So cool how much history NYC has—even more than I already knew!

    1. Jackie Sills-Dellegrazie

      So much history, Miranda! The layers from each time period are fascinating. I know a ton about Dutch NYC but it was cool to see how Dutch sites figured into Revolutionary history.

  5. I wish I’d taken this tour when I was in NYC. You’re right, I only knew about Hamilton because of the Broadway show. I joined the onsite lottery everyday while I was there but I was never lucky. He’s such fascinating man!

    1. Jackie Sills-Dellegrazie

      So fascinating, Aleah! Keep the tour in mind for your next NYC visit. We both still may be waiting to get out hands on Hamilton tickets! 😉

  6. Tours with Context Travel are filled with such history and depth – like you said, thematic field trips. I’ve gone on Context Travel tours in Paris and Bangkok and have impressed. This one in New York and story of our founding fathers and nation sounds incredible. I’m all for learning and touring at the same time. Thanks for sharing this particular Context Travel tour.

    1. Jackie Sills-Dellegrazie

      Totally agree, Rosemary. Travel is the ultimate learning tool and when you can tour with an expert, it’s that much more in-depth. I’ll definitely have to check out their tours in Paris and Bangkok. 🙂

  7. What an awesome guide. I definitely missed most of this on my trip to NYC. I was all caught up in the new, the big buildings and the art, that I totally didn’t even think about Revolutionary War history. I did make it to Trinity Church, which was beautiful, but my brain stopped on history there. I won’t make that mistake next time!

    1. Jackie Sills-Dellegrazie

      So glad you made it to NYC and Trinity Church, Paige. Next time, you can layer the history on! 🙂

  8. Sounds like a really great tour – I think you’re right – I’ve been to New York so many times, but didn’t pick up on any of the sites from colonial / revolutionary times – so it’s definitely about knowing where to look. I love that Context tours never have more than 6 people on it, – makes it feel less like a tour and more like a group of friends exploring. And I love that you can ask as many questions as you want and have in depth conversations. I had no idea that New York was settled first by the Dutch – learned quite a lot of new things today!

    1. Jackie Sills-Dellegrazie

      You’re not alone, Megan. Not many people know that Dutch first settled NYC. It’s all been glazed over to the British 13 colonies. I so agree about asking questions as a major perk of a small group tour. You have access to the guide so it is more of a discussion that being talked at…Context Travel has something in common with the best teachers, I guess! 😉

  9. This is something I didnt imagine for New York. This is something unique and different tour. I would like to experience when I visit this city. This is really interesting, to walk back from the past and learn the history.

    1. Jackie Sills-Dellegrazie

      Totally, Cai. If you don’t know where to look, you walk right past and never realize how much Colonial and Revolutionary history NYC has. Hope you can visit soon!

    1. Jackie Sills-Dellegrazie

      Can’t go wrong with either of those cities, Ollie. Hope you can visit soon!

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