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

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Conceived in the ‘70s and opened in 2012, Four Freedoms Park was well worth the wait. This Roosevelt Island park is an FDR-dedicated memorial positioned on the island’s southern tip, featuring a striking granite deck and hosting events ranging from kite flying to readings to yoga – plus there are stunning views of Midtown Manhattan, home to the Empire State and Chrysler buildings.

Full disclosure: Roosevelt Island comes with a somewhat spooky backstory, a key point of which can still be observed – from a distance. Opened in 1856, the island’s Smallpox Hospital – also known as the Ruin – is where patients infected with the contagious disease were once quarantined; it now stands in ruins. However, the off-limits attraction is still viewable from behind a fence, with only the colony of nearly 100 feral cats that have taken over the building allowed to pass.

The Roosevelt Island Tram is consistently credited as one of New York’s most underrated attractions, and for good reason. For just a swipe of your MetroCard, this decades-old institution whisks you through the air on a journey from Roosevelt Island to Manhattan’s Upper East Side, providing bird’s-eye views of the East River and city skyline on a commute that’s both efficient and enjoyable – really.

To see some of the best contemporary art around, you’ll have to take to the sea. Or, rather, the East River, where RIVAA (Roosevelt Island Visual Arts Association) exhibits works by some 35 artist members alongside international guest artists. Whether you’re interested in photography, painting or live music, you’ll find your fix at RIVAA.

We know, we know: we’re meant to be discussing what to do on Roosevelt Island, but we couldn’t help but notice the panorama! From Roosevelt Island’s west side, you’re afforded a front-row view of Manhattan’s Midtown and Upper East Side, not to mention one of the most famous skylines in the world. So, snap away – the island will understand.

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Lighthouse Park is easy to find on any Roosevelt Island map – it’s at the northeast tip of the island (about a 20-minute walk from the tram). If you find yourself here, look out for the Blackwell Island Lighthouse. The 1872-built Gothic Revival structure, which has the honor of being on the National Register of Historic Places and a New York City Landmark, used to light the old New York City Lunatic Asylum (one tale even claims it was built by an inmate). It now provides a picturesque backdrop for locals relaxing on the lawn.

As you can likely tell by now, Roosevelt Island is a perfect balance of old and new. No place exemplifies this point better than the Octagon, a mid-19th-century structure that was converted into high-end housing in 2006. Even richer than the building’s current tenants is its history. For example, Charles Dickens wrote about its stately main staircase, and multiple fires affected its facade. It was once the entrance to the old asylum, which was opened in 1841. Before its conversion, the five-story rotunda, which was made of stone quarried from the island, was rather un-loved following years of decay.

History buffs won’t want to miss the bragging rights that come with a visit to Blackwell House. The 1796-built clapboard farmhouse, one of the oldest houses in New York City, was added to the National Register of Historic Places in 1972. The refurbished house has been opened up to the public, and exhibits tell the story of Roosevelt Island and the buildings that are no longer standing. Entry is free.

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