Finding Cats, Heroes and Confidence At Roosevelt Island
How an island rich in history made me appreciate how far I’ve come
Prologue
One Saturday in the middle of May a couple of us content creators got together in Chinatown for a networking event. We spent four hours catching up with familiar faces and making new friends. While the gathering was fun on its own, it was the “after-party” that I enjoyed the most. A group of us spent the evening going from spot to spot trying out ube, pork, skewers and enjoying the sights and sounds of a historical NYC neighborhood draped in darkness. It was one of those magical nights you tell your friends about for years to come. As the evening came to a close, one of the more experienced creators turned to me and asked, “So what’s the next big stream?”
When I first started watching IRL (short for “In Real Life”) streams most of the creators I followed were based in NYC. While all of New York has its charm and beauty, Midtown stands out as an epicenter of culture, creativity, entertainment and energy. The flowing crowds, art installations and cultural events make Midtown the perfect backdrop for a livestream on Twitch. Watching these streams motivated me to spend more time at the landmarks that these creators showcased on their platforms. In October of 2023 I decided that I was not satisfied by simply visiting these locations by myself, I had the urge to bring along an audience of my own.
Naturally, I stuck to what I knew best. A lot of my earlier streams centered around Times Square, Bryant Park, Rockefeller Center and Columbus Circle. Of course, there were a few exceptions. I made a couple of visits to the 9/11 Memorial and spent quite some time enjoying the live musical performances at Washington Square Park. While visiting these places for the first time on stream was plenty exciting, several months into my creation journey and the content felt repetitive. I needed something that would both excite my audience and motivate me.
Fresh off the heels of two parades (St. Patrick’s and Easter) and after being live during the 4.8 magnitude earthquake that struck the city in April, I decided it was time for a change. I had spent most of the day during those three streams on 5th Avenue, and while all of these events were exciting in their own right, having the same backdrop for all three made me sick of being in Midtown.
I grabbed my selfie stick and after a couple hours of research made my way down to Chelsea. Walking The High Line (an elevated train line that was transformed into a public park) was a major turning point for my channel. It was a viewer’s recommendation that I was able to turn into a reality, which made me very happy. More importantly, though, it made me realize that the kind of engagement I wanted from chat was only going to come from having content that was more distinct from what I had done in the past.
Weeks after walking The High Line I made a trip down the west coast of Manhattan on my way to see The Intrepid (an aircraft carrier that serves as a museum) which caught the attention of many of my peers on Twitch. Not only did they enjoy the livestream, I got a lot of positive feedback on the highlight video of that day that I published on YouTube.
As the creator networking event drew closer I resolved to do one more big stream. For my first stream outside Manhattan I would cross the Brooklyn Bridge on foot. I made my plans known, from then on out I only wanted to do things on stream that I had never done before. When the creator I mentioned earlier asked me what my next big stream was, little did he know his own travels around NYC had inspired me to go somewhere special.
Inspiration is the name of the game as far as IRL streaming is concerned. It is very unlikely that someone who starts streaming now is going to reinvent the wheel when it comes to how things are done in this space. Streamers in the same city are likely going to visit the same locations, attend the same events and even share the same audience. However, every creator has a distinct perspective that sets them apart from the rest of the crowd.
Without a speaker blaring music or sound alerts, my content relies heavily on my ability to narrate the experience in front of the viewers eyes. My love of history and art sets me apart from some of my peers who rather live in the moment or prefer the viral over the aesthetic. This is why even though I wanted to do something entirely unique for my next big stream, my inspiration was the visit to Roosevelt Island that my peer had made several months before. I knew that my take on this tiny underrated island on the East River would be unlike anything the IRL audience had seen before.
I knew next to nothing about Roosevelt Island. As a matter of fact, I had completely missed my peer’s livestream from the island a couple of months ago. What I did know was that the island was mentioned by both that streamer and their chat constantly. There was something on that island that captivated IRL viewers, I just had to figure out what it was. Although our streamer friend tried his best to point me in the direction of different landmarks on the island worth visiting, my brain struggled to absorb any information after nearly 6 hours of nonstop socializing. In the haze of adrenaline I managed to make out a few keywords:
- Tram
- Park
- Smallpox (???)
Unfortunately it would be another ten days before I could start to unravel the mystery of Roosevelt Island.
The Plan
After a brief illness I woke up one morning determined to stream. Travel is stressful whether you’re streaming or not, but getting around on those days following a period of sickness is particularly anxiety-inducing. “Am I going to have access to a restroom?” “Will I be able to get home in a timely manner if my condition worsens again?” These are questions I’ve unfortunately had to ask myself on more than one occasion during my journey as a livestreamer.
Indeed, many viewers would be surprised to learn the extent of my poker face, having streamed in the midst of illness, fear and even heartbreak. However, this particular morning I felt no worry whatsoever. This happens from time to time and if I had a way of figuring out what puts me in this carefree mood I’d happily trigger this state of mind before every single stream. I knew this morning was special and I had to capitalize on it.
I had already gone live once after the networking event, again in Midtown breaking down the events of the past Saturday for those who weren’t able to attend and visiting the recently re-activated Portal (an art piece allowing people in Dublin, Ireland and Flatiron Plaza to interact with each other via webcam). Starting yet another stream near the TKTS stairs in Times Square felt like taking a step backwards. Then I remembered… Roosevelt Island.
I had not only mentioned Roosevelt Island to all those people at the after-party, I had also brought it up on stream. I have a hard rule against promoting streams and not following through. So, in order to hold fast to my self-imposed rule and to capitalize on the chill mood I was in, I decided it was time to pay Roosevelt Island a visit. One small problem — I still knew next to nothing about the island itself.
I was on the fence again. Sure, I had stumbled into situations where I had no idea what was going on before only to be rescued by some very helpful chatters who were willing to do research on the fly. However, the majority of my most recent streams had included some degree of research. I had a rough idea of the different art pieces I wanted to see on The High Line. I had a couple of facts on hand about the opening of the Brooklyn Bridge before crossing it. I knew enough about The Intrepid after visiting the museum as a child to keep some new European viewers entertained. Not wanting to enter a potentially successful stream entirely blind I turned to one of the world’s greatest resources of information, YouTube.
The last time I relied on YouTube for help on these sorts of matters I found a video from a former Twitch streamer. He highlighted certain entrances/exits to the Brooklyn Bridge that turned out to be very convenient when it came time to exit DUMBO and enter Chinatown while live. Watching someone go through the steps of finding these locations in real-time made it much easier for me to absorb the information than simply looking at a map. This surprised me, as I had never been much of a visual learner.
While still in shock at how much I had changed since the days when simple text or a map would suffice, I nevertheless searched for Roosevelt Island on YouTube, hoping that I would strike gold and make my way across the East River with enough crash course knowledge to deliver at least two hours of engaging content.
I still credit Manny’s video as the reason I decided making the trip was worth it. Manny Explores — a travel YouTuber who’s content centers primarily around NYC — has apparently made several videos from Roosevelt Island, one of which showed up as the first result on my YouTube search. I don’t know if it was Manny’s unassuming nature or the way in which he moved around the island with total ease (probably a combination of the two), but I instantly knew this was something I could pull off. After cramming a few tidbits of information about the island’s north and south ends I was ready to make the trip.
Getting There
Getting to Roosevelt Island isn’t particularly difficult. Of course, you can always make your way to 2nd Avenue and board the tram located between 59th Street and 60th Street. I opted for a more conventional mode of transportation — the F train. I knew that foregoing the amazing views that the tram could offer was a big risk, but I needed to know how reliable the F train was in case I had to make a quick exit off the island. If anything I could (and did!) ride the tram back into Midtown from the island towards the end of the stream.
It was a short ride from Midtown to Roosevelt Island. Upon exiting the F train I realized just how beautiful the station actually was. It bore no resemblance to the dark and often dreary train stations I had become accustomed to in the rest of NYC. Honestly, the only other station that bore any resemblance was World Trade Center Station beneath the Oculus in the Financial District. I took my time making my way to the exit. Indeed, it seemed like no one else who had arrived along with me was in any sort of rush. Stepping out of the station I immediately recognized the mosaic across from me as the one Manny had pointed out in the beginning of his video.
I crossed the street and took a left. Now I was directly under the Queensboro Bridge. I nervously made my way down a street with no clear pedestrian path as several vehicles moved past me. It wasn’t long, however, before I came across a couple of benches and a pair of locals pushing strollers down the sidewalk. Unsure of how long it would take me to get from my current location to one of the key spots on the island, I decided to sit down, set up my tripod and go live anyway.
Going Live
The opening shot is a gorgeous view of the Queensboro Bridge stretching from the top right hand corner of the screen across the East River and into a neighborhood my audience was all too familiar with. I still had Manny on the mind as I pressed live and made sure to credit him and our streamer friend for all their help during the first few minutes of the video. Less than twenty minutes into the stream and I had already come across the first landmark on what would become a long journey up and down Roosevelt Island.
The FDR Hope Memorial
Roosevelt Island gets its name from America’s longest serving president, Franklin Delano Roosevelt. As I approached the FDR Hope Memorial I rattled off a few facts I learned in middle school about the U.S.’s 32nd Commander In Chief. I told my audience — many of whom are not Americans — that FDR had been stricken with polio, which left him wheelchair bound and how the media — in a gesture of empathy that would be entirely unheard of in today’s political climate — did their best to hide the president’s medical condition from the public.
As I circled the two statues — one of FDR in his wheelchair stretching out his hand and the other of a disabled girl in crutches reaching out to him — I couldn't help but be touched by a quote engraved on the ground in front of them.
“All communities become more like Roosevelt Island: accessible, inclusive and welcoming”.
The path preceding that quote was filled with engravings highlighting different laws passed in order to make the lives of disabled Americans easier.
Most Americans are familiar with the concept of a propositional nation: that the U.S. was founded on the principles of freedom and equality for all individuals that call its territories home. However, this was the first time I had encountered a propositional neighborhood, one dedicated to making sure the needs of its disabled inhabitants are acknowledged and addressed. Two weeks after my visit and the aforementioned quote still pops into my mind every now and then.
After exiting the memorial I made my way over to a set of very comfortable reclining chairs. Sitting back I could imagine what it would be like to be there all on my own, without having to worry about entertaining chat. With a great view of the Manhattan skyline straight ahead one could easily spend an afternoon there gazing across the water, contemplating life.
If there's one thing I love about Manhattan its the hustle and bustle. There's always something going on. However, as I sat there on an island filled with thousands that felt eerily empty, I could almost sense time come to a stop. It had been a hectic couple of weeks, in between a demanding stream schedule, social engagements, falling ill and the near-dissolution of a very close friendship, this was the first time in months that I truly felt at peace. Remembering my obligation to the audience still tuning in, however, I got up and made my way to the southern end of the island.
The Smallpox Hospital
I practically ignored one of the most significant pieces of history on the island as I walked over to the Four Freedoms Park, which was unfortunately closed. Turning back around, chat was able to spot the Smallpox Hospital before I had a chance to properly introduce it.
Opening in 1856, the 100-bed hospital was an attempt to quarantine patients affected by smallpox, which still ravaged New York despite the availability of a functional vaccine. Today only the ruins of the hospital’s exterior remain. My mind instantly drew a parallel with the present day and as I turned the camera around to film a segment for YouTube I couldn’t help but mention the extant coronavirus pandemic.
The ruins are an eerie sight. They reminded me of similar structures that can be found throughout the game map of Red Dead Redemption 2, which I fully played through on stream. As a lover of history I oscillated between feeling creeped out and privileged to be able to see a forgotten remnant of history with my own eyes.
The Cat Sanctuary
We were in desperate need of a palate cleanser and the cat sanctuary delivered just that. Up until then the only wildlife I had come across with great frequency were the geese. The island is teeming with geese who feel right at home standing just feet away from the humans walking about. These cats move freely in and out of the sanctuary gates. Some of them rushed past me when a shirtless jogger (who I tried my best not to record) stopped to talk to one of the staff members of the sanctuary.
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As I made my way over to read a display about the island’s wildlife another cat came over and laid down right in front of me. Naturally, these cats melted chat’s heart and if it were up to me we would have spent much more time getting to know our new friends. However, I realized we were racing against the clock when it came to my phone battery so I hurried along towards the next destination.
Walking past Cornell Tech, I could feel the vibe of the island shifting. The closer to the center, the more it resembled mainland Manhattan with one glaring exception. Absent from the island were the major fast food chains that adorn the rest of NYC’s streets. A Starbucks and Subway were the only examples of New York consumerism I could find on my way to Main Street. As I attempted to make it to the north end of the island, I had no idea I was about to come across a structure that had been standing since the 1700's.
Blackwell House
Before the City Of New York took control of the island, Roosevelt Island had changed hands — and names — multiple times. Archeologists credit the Lenape, a group of Native Americans from the Northeastern Woodlands, as the island’s first settlers. In 1637 the Dutch purchased the island from the Lenape and commanded the territory until their surrender to the British in 1664.
In 1668 British military captain John Manning acquired the island for a brief five-year stint until the Dutch retook ownership and forced Manning to live on the island as punishment. The island took its name from the exiled captain, becoming Mannings Island. Manning’s stepdaughter became the new owner and after marrying, ownership was transferred to her husband, Robert Blackwell, who’s family settled the island for over four generations.
In 1796, Robert Blackwell’s great-grandson constructed a wooden home on the island that now bore his family’s name. As I crossed the street I could not believe I was standing in front of one of Manhattan’s oldest homes. The house still looked to be in great condition (from the outside at least).
Unfortunately, signal issues — which had become more persistent since moving closer to the island’s core — prevented me from fully appreciating Blackwell House with my viewers. Chat would later inform me that the house had also been used as a living quarters for wardens of the various institutions that once called the island home, such as the penitentiary and the almshouse.
The Chapel Of The Good Sheppard
Moving beyond Blackwell House, I could immediately tell we were entering a more residential area. The streets, which had been practically desolate since I arrived now saw a slightly greater movement of people. Tucked away from the island’s more aesthetic extremities, this region resembled some of Manhattan’s more quieter neighborhoods. An art gallery, a deli, and even a laundromat gave this section of Roosevelt Island a quaint charm comparable to that of Manhattan’s northernmost streets.
Construction noise near the Chapel Of The Good Sheppard made me feel right at home. I took the opportunity to rest my legs, summarize the day and welcome in new viewers while sitting at the tables in front of said chapel. Then, walking past a modern looking restaurant that promoted live jazz music on one of its posters, I continued my journey to the lighthouse.
Jack McManus Field
Past the supermarket and beyond some small art displays was Jack McManus Field, best described as “a soccer field with a view” (due to the skyscrapers visible in the distance) by one of my audience members. It was one of the only outdoor recreation spots that I had come across on the island.
Tucked away from the rest of the street by vegetation, the field’s entrance was adorned with metal archways that instantly caught my attention. I actually hesitated, as the thought of being all alone in a soccer field seemed kind of depressing to me. To my surprise, there was a small group of men kicking a ball around deeper into the field. I sat at the bleachers and contemplated out loud if I would be able to live on an island so far away from the restaurant chains that I had taken for granted in mainland Manhattan.
Emergency vehicles were a common sight on the island. I passed by a number of police cars, spotted an ambulance near Cornell Tech and as I walked past the rest of Jack McManus Field I could see a number of fire trucks in a lot across from me. It was comforting to know that the island, tiny and peaceful as it was — could respond to any emergency in a timely manner. Looming behind Pony Field (another near-empty park) was a sight that would quickly become discomforting the more I learned about it.
The Octagon
The first thing that stood out to me was the white façade. The color and size were unlike anything else I had spotted on Roosevelt Island. Then I noticed the grey dome, adorned with an American flag flowing in the breeze. “This must be a government building of sorts”, I thought to myself. The theory made perfect sense to me. Blackwell House was too tiny and antiquated to host any significant political presence. If there was some degree of authority on the island, it must be housed in that gigantic and ornate building. Little did I know I was heading towards The Octagon, a residential building with a very dark past.
The name “The Octagon” is actually a reference to the distinctly shaped tower that serves as an entrance to the attached residential building. When the City Of New York acquired the island it did so with the purpose of housing prisoners and the mentally ill. The Octagon, a decade after the construction of the island’s penitentiary, opened as an asylum. I’ve never been one to give in to superstition or pay any great mind to the supernatural, but there was a palatable negative vibe to the place.
Although it seemed like chat agreed with me, The Octagon — with its 500 residences — houses grills, tennis courts and a private pool. Something made me wonder if this was an issue of class. If there was a certain callousness that allowed those who could afford the luxury apartments to compartmentalize the evils that went on at that location (which we will talk about more later on!) and the easy living that they now experienced.
The Girl Puzzle
I was still on the lookout for any familiar sights from Manny’s video on my journey towards the lighthouse. I had a hazy memory of bronze head statues, which I mistakenly thought were in the Four Freedoms Park that I had been unable to enter earlier. However, as I approached the island’s northernmost tip, I realized that the heads were right in front of me.
The round mirrors and bronze heads adorning the north of the island are a monument in memory of journalist Nellie Bly. The Girl Puzzle, by American artist Amanda Matthews pays homage to the enterprising reporter of New York World newspaper fame who went undercover at the aforementioned insane asylum to expose abuses and injustices at the hands of asylum staff.
Nellie Bly’s 1887 book, Ten Days in a Mad-House, chronicles her epic journey through the city’s archaic mental health system. It shows how she successfully convinced many individuals in said system that she was mentally ill despite being of sound mind and how her — as well as the other patients of the asylum — were mistreated. It is definitely a tale worth further exploring if you have the time. I did not expect to come away from my trip to Roosevelt Island with a new personal hero, but Nellie Bly’s name is one that I will hold in high regard for the rest of my life.
The Lighthouse
I couldn’t help but become a bit emotional as I approached the lighthouse. In August of 2023 I stood in front of the first lighthouse I had even seen in person. The Little Red Lighthouse sits just under the George Washington Bridge in Manhattan. Also known as Jeffrey’s Hook Light (after the section of the Hudson River by the same name) the thick red structure bore little physical resemblance to Roosevelt Island’s lighthouse. However, both lighthouses have come to mark very special moments in my life.
In the summer of 2023, certain personal circumstances forced me to be outside of my home for many hours during the day. Although I could come back home in the evenings, I had nowhere near the level of comfort I enjoyed for most of my life, having to sometimes sleep on the floor and wake up before sunrise. This was an emotionally and physically trying period in my life.
Having never been confronted with a situation like this before, I was understandably aimless. I passed my time visiting the local parks in my neighborhood, sometimes walking in circles to alleviate boredom. Eventually, I decided I was going to capitalize on the free time available to me and start visiting some of these landmarks that I had seen on other livestreams.
Being able to make content out of these travels was an unforeseen benefit. Actually, I had been in a bit of a panic during this time, as I had to put my desktop streaming career — which had just started to see some success — on hold for several weeks. I started off slow, visiting Times Square and several city parks nearby. However, it was my trip to The Little Red Lighthouse, a journey through wooded areas and an isolated Manhattan coast, that showed me I had the wherewithal to go anywhere and do anything. As I tipped my phone up and snapped what I still consider to be one of the best photos I have ever taken, I had unknowingly begun a journey that would bring me right to the edge of Roosevelt Island.
It was those miles-long walks around the city, kicked off by the journey to The Little Red Lighthouse, that helped bring my body and mind into a kind of shape that I could be proud of. That ensuing confidence allowed me to go on all the adventures that the latter half of 2023 and the past few months of 2024 have seen me undertake.
As I stood there in front of the Roosevelt Island lighthouse, I couldn’t help but feel that I had reached another checkpoint. I had a consistent audience, those who I had spent the last four years watching now considered me one of their peers and I had officially shed the old mold of running around Midtown holding my cell phone in my hand for two measly hours. If I walked away from it all then and there — something I had seriously considered given how challenging the past two weeks had been — I could hold my head high with pride in all that I had accomplished.
My streams are often filled with these sentimental moments. My first proper stream started in front of the Empire State Building, which housed some of the first radio shows I ever listed to. I was awestruck seeing the Rockefeller Center Christmas tree for the first time in person — mostly because for years it had been a tradition for me to watch the lighting on TV with family. Visiting the Intrepid for the first time as an adult was so special because I could still remember posing for a photo in front of it as a child with a family member that has since moved very far away. Before crossing the Brooklyn Bridge for the first time I paid a visit to the DUMBO neighborhood where a trip there two years prior with my closest friend reignited my love of photography. It was no surprise then that my brain drew an instant parallel between the two lighthouses and what they mean to me.
With little battery left on my phone I had no other choice but to scurry back near The Octagon and catch one of the free red shuttle busses. This marked another first for my stream. Taking public transportation while live in Manhattan is not a wise decision. Signal is inconsistent — at best — on the subway and busses can be both slow and crowded in more populated areas. However, I knew I wanted my audience to see the entire tram ride back to Midtown and I wasn’t sure if chat — or even I for that matter — had the energy for the entire walk back.
As I fitted a charging case to my phone I could tell the shuttle bus driver was very experienced. The bus moved speedily throughout the island, coming to various quick stops at key spots. It wasn’t long before I was thanking the driver for the ride and dismounting in front of the tramway. One of the most exciting experiences of my life was just feet ahead.
The Tram Ride
I swiped into the tramway station with my MetroCard and waited alongside the growing crowd. As I tried to pass the time at the station an old friend “raided” me. Raids are when one creator ends their stream and sends all of their viewers over to another channel. I was ecstatic to have an even larger audience for the tram ride. I greeted many of the familiar faces coming into my channel and summarized the past two hours for them. One very astute chatter recommended I wait for the second tram in order to get a better seat at the front. I hesitated — I was exhausted and anxious to end stream — but ultimately followed her advice.
The doors of the second tram opened and I hurried to get a front row seat. Contorting my body a bit (the seats face inwards for some reason) I was able to give chat a great view of what lied ahead. I hadn’t been on a tram before and didn’t know what my reaction would be. I never thought myself someone afraid of heights, but when I had gone to see the Intrepid just weeks prior I found myself gripping the rails that separated the walkway from the vast water below for dear life. The last thing I wanted was to embarrass myself — not only in front of the tram filled with strangers — but in front of the now much larger audience watching along on Twitch.
As the tram lifted and dangled us right above the East River I felt nothing but ease. The state of total relaxation that I had woken up with that morning had thankfully lasted all the way through to this moment when I was at the same height as the Queensboro Bridge. One viewer pointed out the skyscrapers that adorn Billionaires’ Row — a neighborhood known for its expensive luxury apartments housed in various supertall buildings.
All in all it was a 5 minute ride back to Midtown. Arriving for the first time at the 2nd Avenue tramway station I could only utter one word that is often-overused on my stream: surreal. Much like that one evening in May when I prowled the streets of Chinatown with some of my favorite creators and viewers, I knew I had come away from an experience that I would be talking about for years to come.
Summary
Nearly two weeks later and I can safely say that my trip to Roosevelt Island changed me.
First, it made me more appreciative of the creators who have come before me. There’s always the allure of being the first creator to an event or location. However, I couldn’t have produced a quality stream without Manny’s video serving as a roadmap for all there was to see on the island.
Second, it instilled in me a greater desire for travel. While I love Manhattan, nothing beats the novelty of streaming somewhere entirely new. My reactions — as significant to the stream as what goes on in front of the camera — could not be what they were if I was merely doing my usual rounds in Midtown.
Third, it made me more considerate of the plight of the disabled. That quote at the FDR Hope Memorial still affects me to this day. Think of how radically different the world would look if we prioritized the needs of the approximately 1.3 billion people around the world who suffer from some sort of significant disability.
Fourth, it made me more appreciative of how far I’ve come. It is undeniable that I both personally and professionally as a content creator have changed tremendously in the last 8 or so months of livestreaming.
Fifth, it made me aware of the importance of taking chances. I had every reason to stay home that day. I was considerably ill just days before, I had only a cursory knowledge of a place I had never visited before and I was reeling from the sudden deterioration of a close friendship. Despite all that I decided to hop on the F train and embark on what has been one of my favorite adventures so far.
Epilogue
As that magical night in Chinatown came to a close the haphazardly assembled posse that had dined and laughed together under scaffolding and streetlights slowly trickled into the the train lines below. Some faces I expected to see again, others I knew were gone for good. When my turn came to descend into the subway and make the slow journey back home, the three of us who still remained turned to each other. The creator who had inquired about my next big stream embraced me and as we stood toe to toe with each other paid a compliment that still rings in my ears so many days later. “I like what you’re doing”. Well, after Roosevelt Island I can safely say I like what I’m doing too.
Thank you for reading. If you enjoyed this story be sure to watch the companion video above and check out my social links for updates, photography and alerts for when I go live.
