New York City Roosevelt Island

Once known as “Welfare Island,” this land was long used to contain New York's unwanted and forgotten—an asylum, a smallpox hospital, and a prison all shared the very limited space here throughout the 19th and early 20th centuries. Famous inhabitants Mae West and Billie Holliday both served very brief time on the island for various misdemeanors. The Goldwater Hospital to the south and the Coler Hospital to the north are living reminders of the island's legacy. In the 1970s, a planned community was established and modern rentals and condos built, lending the island its somewhat artificial look. Divided into Southtown and Northtown, Roosevelt Island houses some 12,000 residents.

Southpoint Park Area, At the island's southern tip, Southpoint Park (open daily 8am-dusk) provides amazing vistas of Manhattan. A promenade runs along it's western edge, offering benches and more views across the East River. The Blackwell House is the revolutionary-era farmhouse of the Blackwell family, who owned the island from 1676 to the early 19th century. Just north, the Chapel of the Good Shepherd, built in the 1880s and frequented by the island's sick during its welfare days, now houses both Protestant and Catholic congregations. Toward the northern tip of the island, you'll find the remarkable Octagon, once an asylum whose conditions shocked Charles Dickens, and later part of the City Hospital. Today, it's the lobby of a huge apartment building. At the northern edge, Lighthouse Park provides views of Manhattan and Queens that center on the 1872 lighthouse, which once assisted boats navigat Take Tramway from 59th St. and 2nd Ave. to Roosevelt Island. Southpoint Park open 8am-dusk.
Tramway, The island is accessible via the F Subway line, but a more exciting option is the Tramway system. The 4½min. crossing from the Manhattan terminal on 59th St. and Second Ave. takes you 250 ft. above the East River and deposits you right in the middle of the island. The bright red trams have become landmarks—you may remember them from the first Spider-Man, in which a tramload of passengers is saved from the Green Goblin's murderous clutches by our web-slinging hero. The tram system was under repair and scheduled to re-open in early 2011. Once on the island, you can travel up and down Main St. on the cheap minibus. One-way pass $2. MetroCards accepted. Trams leave every 15min. M-Th 6am-2am, F-Sa 6am-3:30am, Su 6am-2am.