The Best Things to See and Do on Roosevelt Island, NYC

The Best Things to See and Do on Roosevelt Island, NYC

Although Roosevelt Island is technically a part of Manhattan, it has long been overshadowed by New York’s Erector-Set Queensborough Bridge. The island was once called Blackwell Island, then Welfare Island, housing insane asylums and prisons, then an outpatient clinic for hospitals, and eventually an UN-run facility. In some ways, the slightly drab, uniform housing (mostly – there are newer condominiums that pop out a bit more) recalls Stalinist housing blocks.

Change is taking place, though. With its riverside walks and unobstructed views of Manhattan’s Upper East Side, Roosevelt Island has always been a nice place to take a stroll with no crowds. However, the recently opened Cornell Tech campus and the new ferry stop have brought a newfound sense of vitality to the island.

While you’re there, here are nine things you shouldn’t miss;

1. The Tram

In one of New York’s most memorable commutes, you can glide over Upper East Side avenues and the East River with the swipe of your MetroCard.

2. Four Freedoms Park

In 1974, Louis Kahn died, and with him, his plans to build a Franklin D. Roosevelt memorial on Welfare Island, his only New York project. A revival of the project was finally realized in 2012 when the Four Freedoms Park opened. Featuring an open-topped deck surrounded by granite blocks, the park certainly makes a good impression. Between May and October, the festival hosts yoga, book readings, kite flying, lectures, and music performances. You can also enjoy the Fourth of July fireworks from this vantage point if you arrive ridiculously early.

3. Smallpox Hospital

Before reaching Four Freedoms Park, you’ll pass the ruins of the first hospital in the country dedicated to treating the infectious disease, the weed-covered Smallpox Hospital, which opened in 1856. Behind the fence, you can still see the aging structure even though you aren’t allowed to wander through the ruins (for safety reasons).

4. North Point Lighthouse

It’s worth exploring both sides of the island. It’s a 25-block walk north from the tram stop or a five-minute walk from the island bus terminus, which is free to ride from south to north. Upon reaching the top of the hill, you’ll see a Gothic revival lighthouse built by the city in 1872 to illuminate the nearby insane asylum. Though the asylum has long gone, there are some shaded lawns and seating areas near the lighthouse that overlook Randall’s Island.

5. Octagon

An island retreat built in the mid-19th century that impressed young Charles Dickens then became a hospital before falling into neglect for years. As of 2006, it has been transformed into high-end housing. As you walk up the winding entry of the ‘flying staircase,’ you’ll see an adjoining gallery.

6. Blackwell House

The clapboard farmhouse has been standing on the island since 1796 as a private residence, known as Blackwell Island after its owners. The house’s interior will be converted into a community center as part of the renovation plans.

7. Art

Near the subway station is RIVAA, a gallery on Main Street with unusual hours (6-9 pm Wednesday & Friday, 11 am-5 pm Saturday & Sunday). Artists from RIVAA also exhibit their works in the OCTAGON Gallery located in the Octagon Building. Sculptures by Tom Otterness titled ‘The Marriage of Money and Real Estate are located offshore near the island’s north end.

8. Roosevelt Island Historical Society

A small visitor’s center is run by the Roosevelt Island Historical Society near the tram terminal in a historic, relocated streetcar entrance kiosk. It’s great merch and includes a heartbreakingly cute, hand-drawn map of Rhode Island.

9. Cornell Tech

With the new Cornell Tech campus opening on the island, as well as the world’s first Passive House residential high-rise, the island will get a whole lot busier. It has striking architecture, open public spaces, and a recently opened hotel. Among Cornell’s food science products, you can find Big Red Cheddar Cheese Curds in the cafe at the campus’s Bloomberg Center.
If you’re visiting New York, there are countless things to add to your itinerary, from the top sights to see and places to explore to the most popular breakfast bars, restaurants, and the best brunch cruises in New York.

Scott is the editor-in-chief of Spice Market New York. He is also an author and publisher of his own craft.