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Exploring Roosevelt Island: The Secret of New York City Unveiled

by Adam Guy

Roosevelt Island? What’s that? Never heard of it. Is that even a part of New York? This is a common reaction I get from guests – certainly from new visitors, but also from frequent travelers to the Big Apple.

Now, keep this to just us… Roosevelt Island is the secret of New York City.


Roosevelt Island Tram

Roosevelt Island has loads of history, views aplenty, and a rare calmness away from the freneticism of Manhattan. It’s two miles long and only about 200 yards wide. It’s a safe and fascinating, family-friendly sanctuary. The island's dark and storied history gives it character, but also might keep people away. Hence the mystery.

Did I mention that I used to live there? I DID... for more than seven years and loved every minute of it.

Brief History

Since the 1820’s, Roosevelt Island was the place where the city of New York would quarantine criminals, the mentally ill, and those with severe diseases. It was an island of prisons, asylums, and hospitals, separated from Manhattan by a dangerous-to-cross East River – perfect if you want to keep the “undesirables” away.

Bust of Franklin Delano Roosevelt on Roosevelt Island

The latter half of the twentieth century saw the island, once known as Blackwell's Island, transform into a new residential area. Adopting a new name in honor of President Franklin Delano Roosevelt, the island started building apartments, schools, and parks.


Today, about 12,000 mixed-income families and individuals call it home. There’s everything you would need on the island, including schools, grocery stores, restaurants, churches, a mosque, ball fields and tennis courts.


Amazingly, some of the dark institutions that were once mainstays on the island STILL exist!  In fact, the mental asylum is still there. Of course, now it’s part of a luxury apartment community. (How New York, right?)

Visiting Roosevelt Island

One of the highlights of a visit to Roosevelt Island is a ride on the Roosevelt Island Tram! The first and one of only two trams in the U.S. that are part of public transportation system, the tram has been in operation since 1976.


While you can get to the island via subway or ferry, the tram is the most scenic way for visitors to get there. It’s also just a cool ride!


Once there, head toward the south end of the island first. There you can see:


Graduate Hotel – The lobby is interesting, and they have funky restrooms. Either Eleanor or Franklin Roosevelt watches as you do your business. ALSO, after 5:00 p.m., the Graduate has an amazing rooftop bar called the Panorama Room. Don’t let the pricey drinks and loud music deter you. The view is stunning!

View from the Panorama Room in the Graduate Hotel on Roosevelt Island

Cornell Tech – This Ivy League annex focuses on biotechnology, health engineering, and computer sciences. There’s a café and restrooms on the first level. The students who go here are “wicked smaht.” Oh sorry… that’s a Boston thing to say.


FDR Hope Memorial – This work by artist Meredith Bergmann is one of the only tributes to FDR in which he appears in his wheelchair.

Ruins of the SMALLPOX HOSPITAL – An incredible landmark that you won’t believe still exists until you see it in person. There’s an incredible story behind smallpox, immigration, New York City, and this building. You’ll just have to come a tour with me to hear it!

Smallpox Hospital Ruins on Roosevelt Island

Four Freedoms Park – The south end of the island honors FDR’s legacy with stunning granite-laced design and larger-than-life bust of the former president. The “room” at the very end offers a place of peace and reflection as you look east at the United Nations and south toward downtown Brooklyn.

This walk should take you 60-90 minutes. If you feel inclined, then head up to the north end of the island. You’ll be able to see firsthand what living on the Island is like. The northern end also has some amazing sights to see including:


The Octagon - former Lunatic Asylum on Roosevelt Island

The Octagon – The main octagonal building is the original building of the Lunatic Asylum… for real!  That structure and the two new buildings flanking each side now make up the Octagon, a luxury apartment complex. You can go inside and have a look, but they have a very strict “no photos” rule.


The Girl Puzzle Monument honoring Nellie Bly – This is the most striking monument in all of New York City. Created by artist Amanda Matthews of Prometheus Art, this collection of sculpted faces celebrates the legacy of one of the bravest, game-changing women in American history. Never heard of her? I’m not surprised. She gets far less attention than she deserves. I could write a whole blog about her moxie and mold-breaking ways. She was a total BOSS! Go to the monument and learn about her. Also note, the placement of the Monument is important, as some of her trailblazing work is connected to the asylum! 

The Girl Puzzle Monument honoring Nellie Bly on Roosevelt Island

Roosevelt Island Lighthouse – This old lighthouse used to help boats find safe passage through Hell Gate, the waters that sit just north of the Island. These once treacherous passageways had rough currents and jagged rock formations throughout and is credited with bringing down roughly 1,000 ships annually. Years of erosion and dredging have made the waterways much safer.

Tom Otterness’s “The Marriage of Money and real Estate” sculptures – Walk back from the lighthouse along the west side and you will see three of Otterness’s works in the water near the shoreline. The sculptures aim to make a statement about New York’s real estate obsession as you stare over at the dense and expensive Upper East Side.

The Marriage of Money and Real Estate by Tom Otterness on Roosevelt Island

Roosevelt Island is a wonderful surprise for sure and should be on anyone’s NYC trip itinerary. I’m biased. I know. That said, I take people to Roosevelt Island for tours all the time. The reaction I receive is consistently: “I never knew this place existed,” I would have never come here without you,” This place is so great and unexpected,” and “I’m so glad we came here!”


This gem is not quite the secret it once was (hence my rent increase), but it’s still off the radar for most vacationers. Now you know, too! 


I would love to show you around my former home island. Ask me about a tour. That’s right I run a tour company called I Know A Guy NYC Tours. Get it?  Adam Guy…. I Know A Guy. Send me an email or shoot me a text or WhatsApp message at 404-915-9901 so we can figure out the best adventure for your family or group. 

I’ve taken loads of families and groups out in the city. (Everyone has survived!) See what they’ve had to say about the experience on Google reviews.

I also post great content about everything NYC – cool places, fun facts, special moments -  on Facebook or Instagram.  Follow along and you may be inspired to finally book that trip to the Big Apple.


I Know A Guy NYC Tours

Thanks for reading this blog! If you would like to chat about your upcoming trip and possible tour ideas, please contact me at I'm quite friendly!

© All photos by Adam Guy


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