A Walking Tour of Brooklyn with Context Travel

Although I’ve lived in New Jersey for most of my life, I’d never visited Brooklyn before as a tourist. Then I found Context Travel, a travel company known for its “Scholar-led Walking Tours of the World’s Cultural Capitals,” and signed up for a walking tour of Brooklyn. 

Brooklyn Brownstones by Avi Werde
Historic Brownstones of Brooklyn. Photo by Avi Werde

I’d recently taken their fabulous walking tour in Barcelona that sampled the city’s chocolates.  Seeing they had a three-hour walk of Brooklyn’s major neighborhoods – “Brooklyn Neighborhood Tour with Brooklyn Bridge and DUMBO” – I immediately signed up.

A Walking Tour of Brooklyn: A First-Time Visitor’s Perspective

As the largest of New York’s five boroughs, Brooklyn was founded in the 19th century as a place for upper-class families to escape the squalor of Manhattan Island.  Today it is home to some of the city’s oldest brownstone apartment buildings, quite lovely, I found, especially when surrounded by the vibrant orange, gold, and red hues of fall.

Brooklyn has an interesting history, which I was looking forward to learning about. This walk focused mainly on the neighborhood of Brooklyn Heights—the historic area directly across from lower Manhattan—and surrounding areas.

Brooklyn Bridge by Colton Duke
Walking across the iconic Brooklyn Bridge Photo by Colton Duke

Discovering Brooklyn: Crossing the Iconic Brooklyn Bridge

Joining a small group of intellectually curious folks from around the world (and around the corner – New Yorkers turn to Context to learn more about their city as well), we set off to learn about the social and economic history, architecture, and the cultural make-up of Brooklyn.

The sunny day was perfect for a walk, which, led by an urban historian, began on the Manhattan side of the Brooklyn Bridge so that we could enjoy the experience of walking across this world-renowned landmark.  It took fourteen years to build it – it’s the first steel suspension bridge in the world.  When completed, it was the second tallest structure in New York, topped only by the spire of Trinity Church on Wall Street.

The city’s skyline is much different today, but the bridge is still magnificent. As we crossed the narrow East River from Manhattan, we learned about the history of the bridge and the history of Brooklyn, which had been an independent city until 1898. Our guide also pointed out Governor’s Island, at the confluence of the Hudson and East Rivers in New York Harbor.


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DUMBO: Brooklyn’s Trendy and Historic Neighborhood

Across the bridge we strolled through DUMBO (Down Under the Manhattan Bridge Overpass),  which has been called “the neighborhood between the bridges”, and although it’s clustered with historic warehouses, factories, and bars, you’ll find some sweeping views of Manhattan here.  That’s one reason why, in recent years, this neighborhood has become very trendy, its warehouses being converted into residential and cultural venues.  Some of its new luxury condos are priced at over a million dollars.

Here we also visited Jacques Torres Chocolate at 66 Water Street, which was among my favorite stops. It’s the dream of a master pastry chef, Jacques Torres, one of the first artisan Chocolatiers in America to make his own chocolate from cocoa beans.

DUMBO, Brooklyn
DUMBO, Brooklyn. Photo by Fabio Fistoral

With over 30 kinds of truffles to choose from, as well as everything else covered in chocolate, making a decision here can be difficult, but fun!

In 1977, violinist Olga Bloom towed Bargemusic, a coffee barge used by the Erie Lackawanna Railroad, to the Fulton Ferry Landing and adapted it for use as a concert chamber.

Next door is the former Fireboat House, once used by the Marine Company 7 of the New York City Fire Department. Today it’s the Brooklyn Ice Cream Factory, prized for its cones and views!

Exploring the Historic Brownstones of Brooklyn

Brightly colored leaves fluttered from the trees as we viewed the spectacular antebellum homes that lined the streets of Brooklyn Heights. Brooklyn’s leafy upper middle class residential neighborhood is so pretty, it has appeared in various movies, such as Prizzi’s Honor and Moonstruck. The entire neighborhood has been awarded landmark status.

Brownstones in Brooklyn Heights. Photo by Lee Snider.
Brownstones in Brooklyn Heights. Photo by Lee Snider.

Here we saw some lovely carriage houses and the Plymouth Church of the Pilgrims, where abolitionist Henry Ward Beecher (whose statue is shown at the top of this page) was a minister for forty years. He’s the brother of Harriet Beecher Stowe, who wrote Uncle Tom’s Cabin

A slew of famous folks shared the pulpit here, including Charles Dickens, and past worshippers included Abraham Lincoln, Mark Twain, Clara Barton, and Dr. Martin Luther King, Jr.

We also passed the 1880s former carriage house where playwright Arthur Miller lived before marrying Marilyn Monroe.

My favorite part of the neighborhood, though, was the Promenade, which runs along the outer edge of Brooklyn Heights. There we joined joggers, dog walkers, and people who just wanted to sit and admire the view of the lower Manhattan skyline.

Concluding Thoughts: A Deeper Appreciation of Brooklyn

I found Context Tour’s Brooklyn, Portrait of a City, to be an entertaining and thorough introduction to one of New York City’s most fascinating boroughs.

Photo by Carmine Savarese

I could have walked around Brooklyn on my own, but by choosing to go with Context, my experience was much more meaningful. There’s something special about a scholarly guide who not only knows the area in-depth but imparts a contagious enthusiasm.

By taking this tour, Brooklyn became so much more to me than just another borough. Now I can go back and explore by myself with a much deeper understanding of the city.


Staying in Manhattan: Personal Recommendations

I stayed at Yotel Manhattan, a trendy hotel on Tenth Avenue at W42 Street.  Their monsoon rain showers and heated towel racks get an A+!  I enjoyed their free WiFi and tasty Dohyo Restaurant & Bar. 

Three of my favorite New York City hotels are Citizen M, the Library Hotel, and the Hotel Giraffe.

Disclosure: I took part in this tour courtesy of Context Travel, but all opinions are my own.

About Melody Moser

Melody is a Travel Writer and Blogger. She loves exploring the world and helping others plan their journeys near and far.