Island of Lost Souls: Madness & Medicine on Roosevelt Island

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The intersections between the history of institutional spaces and the urban folklore that surrounds them

Now a pleasant, tight-knit residential community, Roosevelt Island was once an island of institutions inhabited by convicts, lunatics, and the destitute.

City leaders in 19th century New York viewed the small East River island as an ideal locale for their social “outcasts,” and filled the island with a smallpox hospital, an almshouse, a penitentiary, and a lunatic asylum. A narrow spit of land surrounded by swirling waters with troublesome currents, Roosevelt Island certainly seemed the place to hide the city’s undesirables away. These days the island retains vestiges of its institutional past, some only recently restored and opened to the public for the first time in decades.

Our tour visits the sites of these former almshouses, hospitals, laboratories, prisons and asylums, beginning with the eerie, romantic, and moody-looking neo-Gothic ruins of the smallpox hospital, moving to the site of the first laboratory in the country focused on pathological and bacteriological research, and finally to the site of the New York City Lunatic Asylum, built in 1841, which reporter Nelly Bly called a “human rat trap… easy to get in, but once there it is impossible to get out.”

Along the way, we will see one of the oldest farmhouses in New York City, built in 1796 and still standing, hear the tale of a criminal housed in the penitentiary so notorious she was referred to as “the monster in human shape,” and find out what happened to the bodies of the approximately 450 smallpox victims who died annually from 1856 to 1875.

And, in true Boroughs of the Dead style, we’ll ask the question that’s on everyone’s minds when they view the looming ruins of the smallpox hospital and the forbidding façade of the former lunatic asylum: is it haunted? Perhaps the sinister 19th century architecture simply begs for such tales, or perhaps there is something more to these rumors: an anxiety about the way we deal with the poor and sick, a fear of being trapped in faceless bureaucratic systems, or a discomfort with our own desire to keep unpleasant things hidden from view.

More than just a historic sightseeing tour, this two-hour walk through Roosevelt Island will investigate the intersections between the history of these institutional spaces and the urban folklore that surrounds them, unearthing the secrets that isolated islands and swiftly moving rivers sometimes hide.

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Tour at a Glance
Start Location:

In front of the Smallpox Hospital ruins inside Southpoint Park

End Location:

Near The Octagon tower at the north end of Roosevelt Island

Tour Duration:

2 hours


1.6 miles

Tour Run Dates:

May - November

Important Information


Important Information


  • Comfortable shoes
  • Weather-appropriate clothing
  • Cash (or your preferred app, i.e. Venmo) if you want to tip your guide


  • Pets
  • Drugs and/or alcohol
  • Film/photography/recording equipment without prior permission


  • Tours run rain or shine, so dress appropriately for the weather! (See our advice here)
  • Wear comfortable shoes! Most of our tours are at least a mile in length.
  • In the event of extreme or severe weather conditions, this tour may be amended or postponed; if postponed you will be given a rain check to take another tour at your convenience.
  • There are no bathroom breaks or rest stops on the tour.
  • Tours start on time, so please try to get to the meeting point 15 minutes early to give yourself time to check in and get comfortable before the tour starts.