Obscura Society NY: Roosevelt Island - Two Hours in a Madhouse - Atlas Obscura
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Obscura Society NY: Roosevelt Island - Two Hours in a Madhouse

Explore Roosevelt Island's fascinating past, from lunatic asylums, to abandoned smallpox hospitals, to pneumatic trash tubes.

A stone's throw from the city, Roosevelt Island couldn’t feel further away from the hustle and bustle of busy Manhattan. But the calmness underlies an eerie past which has been obscured by 100 years and multiple makeovers. Join guide Mark Sikes for a walking tour to uncover some of Roosevelt Island’s hidden secrets. 

A place of many names, what we know now as Roosevelt Island was once the home of an insane asylum and a penitentiary that imprisoned such figures as Billie Holiday, Mae West, Emma Goldberg and Boss Tweed. We will visit the ruined asylum’s historic Octagon Tower, see the last remaining walls of the penitentiary, and visit the island's original street car kiosks.

Plagued by decay and urban blight throughout the 1960s, the island was re-envisioned in 1969 as a utopian island with no cars, soviet-style housing towers, an ariel tramway, and a pneumatic trash system. We'll view the architecture from the Tram as we ride over, and take a walk down Main street that will make you feel like you're walking through a Robert Moses/World's Fair Futurama. 

 Meeting location:

Roosevelt Island Tramway plaza on the corner of 60th Street and 2nd Ave. Closest subways are the 456 and NRQ at 59St/Lexington Ave. Dress appropriately for walking and weather.