New York
Roosevelt Island Tramway & Self-Guided Ridiculous History Tour
Fly over the East River to the weirdest two miles in NYC. Forget the polished tourist traps. Grab your MetroCard (or OMNY) and ride the "Flying Red Toaster" (the Tram) to the former home of New York's convicts, lunatics, and smallpox patients. This self-guided audio adventure starts with a flight above the traffic and lands you squarely in the middle of "Welfare Island." We'll walk the promenade, investigate the creeping ivy of the Renwick Smallpox Hospital ruins, and stand in the shadow of the asylum that investigative journalist Nellie Bly exposed. You'll also encounter "The Girl Puzzle"-a haunting monument to Bly and the women who suffered in the asylum she got herself committed to. It's a mix of dystopian history, skyline views, and the kind of bizarre facts you can only find in New York. Highlights: The Tram Ride: Get the best aerial view of the city for the price of a subway swipe. The Ruins: Get up close to the haunting, crumbling walls of the Renwick Smallpox Hospital. The Asylum & The Girl Puzzle: See the tribute to the woman who faked insanity to reveal the island's horrors. The FDR Memorial: A massive, surprisingly intense monument at the tip of the island.
Expected Tour Length: 2 hours 5 mins
Number of Stops: 14
Tour Type: 🚶♂️ walking
Key Locations
- • Roosevelt Island Tramway
- • Franklin D. Roosevelt Four Freedoms State Park
- • Smallpox Memorial Hospital
- • Cornell Tech
- • The Octagon
- • The Girl Puzzle Monument Honoring Nellie Bly
Includes
- • Private tour, completely controlled by you!
- • Pintours App allows for full personalization.
- • Pause or skip any stop on the tour.
- • Unlimited free time, stay as long as you want
- • Free access to secret info per stop
Highlights
Designed By
Robert Hillebrand
I’m Robby, a dedicated cycling enthusiast and history detective obsessed with uncovering the strange, forgotten, and truly radical stories of New York City. My years as a bike messenger gave me an unparalleled, street-level intimacy with NYC's grid—a critical background that allows me to meticulously curate routes that are not only safe and accessible for all skill levels but designed to immerse my guests in the city's authentic, often bizarre, local culture. My tours specialize in the crucial, yet little-known, histories that transform NYC from a mere destination into a living, breathing origin story.