Discover the fascinating history of Roosevelt Island, from a sliver of farmland off of Manhattan to the home of New York City’s unwanted: prisoners, the mentally ill, and those with contagious diseases. On this walking tour, I’ll show you the island’s southern end where I’ll unpack some of its complicated 400-year-long history. Having grown up on Roosevelt Island, I love sharing the amazing history of this place and how it was transformed from the island of the unwanted into a thriving community. While you walk, you’ll see what’s left of its uncomfortable past and find out how hospitals and penitentiaries were replaced with the fabulous Southpoint Park, Cornell Tech facilities and Franklin D Roosevelt Four Freedoms State Park. On this 30-minute tour, you’ll also: • See the iconic Roosevelt Island Tramway, the first commuter tramway in the country • Hear about Captain John Manning, the island’s first owner, who was sentenced to permanent exile there • Find out about Blackwell Penitentiary, where Billie Holiday was held for a while • Take in the remains of the Smallpox Memorial Hospital, the only ruin in the city’s National Register of Historic Places • Stroll through the beautiful FDR State Park to the magnificent bronze Franklin Delano Roosevelt sculpture Join me on this half-mile tour to discover the island’s history while enjoying the backdrop of Manhattan’s skyline.