Known decades ago as Welfare Island, thanks to its assortment of hospitals, and before that as Blackwell Island, when it was home to an asylum, a prison, and even more hospitals, New York City’s Roosevelt Island hasn’t always been a popular attraction.
But in recent years, this tiny island in the East River has become a quick, easy escape from the urban sprawl, boasting green spaces, historic landmarks, a chic new hotel with an even chicer rooftop bar, and an aerial tram with incredible views of Manhattan’s Upper East Side. Here are the best things to see and do while you’re there.
Roosevelt Island tram: a commute with a view
Giving the Staten Island Ferry a run for its money as one of the best ways to see New York's sights without breaking the bank, the Roosevelt Island tram glides over Upper East Side avenues and the East River, offering one of the city's most memorable commutes – all for the swipe of a MetroCard. Watch this 60-second video with a driver who's worked for the tram since it opened in the '70s.
Four Freedoms State Park: an unconventional Presidential memorial
When architect Louis Kahn died in 1974, so did plans to build his only New York project, a memorial to Franklin D. Roosevelt on the southern tip of what was then called Welfare Island. Fortunately, it was eventually revived: Four Freedoms State Park opened in 2012, and it's a sight to behold, comprising an open-topped deck lined with tall granite blocks. The park's event season runs from May to October and includes yoga, book readings, kite flying, public talks and music performances. (It’s also a great vantage point for the Fourth of July fireworks if you’re willing to get there obscenely early to snag a spot.)
Smallpox Hospital: a relic from the island's former life
Just before you reach Four Freedoms park, you’ll walk past the ruins of the weed-covered Smallpox Hospital, which, when it opened in 1856, was the first hospital in the country dedicated to treatment of the infectious disease. Though you aren’t allowed to wander through the ruins for safety reasons, you can still get a good glimpse of the aging structure from behind the fence.
The Graduate Hotel: the best – and only – hotel around
The island's sole hotel, the Graduate pays tribute to the rich history of its surroundings, with a hallway on the first floor dedicated to photographs of the Roosevelt family and a copy of FDR's famous "Four Freedoms Speech" in every guest room. A nod to its location at the center of Cornell Tech (more on that later), the first-floor lobby and adjoining area are lined with more than 10,000 textbooks, all of which were donated from the school. Just off the lobby is the island's newest restaurant, Anything At All, which takes a farm-first approach to contemporary comfort food. (Its name is a reference to a line in The Great Gatsby, for all you bibliophiles.) Topping it all off, quite literally, is the Panorama Room, a rooftop bar offering stunning views of Manhattan, Queens and beyond.
The Lighthouse: a north-point attraction
At just 1.75 miles – or 35 city blocks – long, it's worth hitting both ends of the island, and the northern tip is a pleasant, 20-minute stroll from the tram (or a five-minute walk from the terminus of the island bus system, which you can ride for free). Once there, you'll reach a lonely Gothic Revival lighthouse, built in 1872 using granite quarried from the island itself – and constructed, legend has it, by a patient at the former asylum. That institution is long gone, but there are some shaded lawns and sitting spots by the lighthouse that look north towards Randall's Island.
The Octagon: a revitalized landmark
A block south of the lighthouse, this mid-19th-century remnant was built as the main entrance to the New York City Lunatic Asylum, and its architecture was so impressive it drew praise from a visiting Charles Dickens. The asylum became a hospital, then fell into decades of neglect beginning in the 1950s, but in 1972, the building was listed on the National Register of Historic Places, and in 2006, it was refashioned as high-end housing. Today you can visit the "flying staircase" up its winding entry, and there's an adjoining gallery.
Blackwell House: a glimpse of 18th-century history
The sixth-oldest house in New York City, this clapboard farmhouse was built in 1796 and dates back to when the island was a private residence (then known as Blackwell Island, after its owners). The interior was renovated in 2020 to restore the building's 18th-century decor.
Artistic endeavors: galleries on Main Street
A couple blocks north of the subway station is Gallery RIVAA, a Main Street salon affiliated with the Roosevelt Island Visual Art Association. It shows pieces by local artists, hosts jazz sessions and poetry slams, and keeps some unusual hours (6-9pm Wed & Fri, 1-5pm Thu, 11am-5pm Sat & Sun). Works by RIVAA artists are also exhibited in the OCTAGON Gallery in the Octagon Building.
Roosevelt Island Historical Society: smart shopping
The Roosevelt Island Historical Society runs a small visitor's center in a historic, relocated streetcar-entrance kiosk, just next to the tram terminal. The merch is great, and includes a heartbreakingly cute, hand-drawn RI map.
Cornell Tech: contemporary architecture...with a side of cheese
When it opened in 2017, the Cornell Tech campus brought an ambitious assortment of buildings and tech entrepreneurialism to this sliver of land in the East River. Among the new additions was the House at Cornell Tech, the first residential high-rise built as a so-called passive house, which requires very little energy. In addition to its striking architecture, the campus also includes two acres of open public space. While you're on the premises, drop into the cafe at the Bloomberg Center to pick up some Big Red Cheddar Cheese Curds, a product of Cornell's Department of Food Science.