A day in the life of a Roosevelt Island tour guide


A tour guide on Roosevelt Island gives visitors an overview of the island’s history and attractions. But that overview is growing as the community raised its profile over the last decade. FDR Four Freedoms State Park opened the south end with style, and Cornell Tech brought in the leading edge of technology.

by David Stone

The Roosevelt Island Daily News

Roosevelt Island Tour Guide.
A Roosevelt Island Tour Guide with his group across from the Tram Plaza.

What are the highlights a tour guide shows visitors?

My first visit was led by a tour guide with Adventures on a Shoestring. We met on 2nd Avenue, paid up and rode a Tram cabin across the East River. Once on Roosevelt Island, we went north because, apart from Goldwater Hospital, there was nothing south.

But times have changed in thirty years, probably more than any other neighborhood in New York City.

This small island in the East River rests on solid rock between Manhattan and Queens, accessible by the Roosevelt Island Tramway, the NYC Subway, NYC Ferry and a lift bridge from Queens. Roosevelt Island is home to many historical and cultural sites, as well as beautiful views of the cityscape.

Sights for a Roosevelt Island Tour Guide:

Start with the Tramway: You can tell how many tourist are in a Tram cabin by the number of gasps heard as the journey lifts passengers above the Queensboro Bridge. Or by the cameras coming out, recording the ride.

It’s a four minute glide that feels briefer because the views rise and fall rapidly. There’s a lot to see.

The Roosevelt Island Lighthouse: One of the most iconic landmarks on Roosevelt Island. The lighthouse was built in 1872 and is one of the oldest structures on the island. A popular spot for photography, it’s a must-see for anyone visiting Roosevelt Island.

Four Freedoms Park: This park was built to honor President Franklin D. Roosevelt and, specifically, his Four Freedoms speech, widely regarded as the modern foundation human rights.

“The Room” in FDR Four Freedoms Park where the walls honor the ideals Roosevelt held up to the world.

The Octagon: This is an eight-sided building that has gone through multiple incarnations. It is now a residential building. Its claim to fame? Once a women’s lunatic asylum, it was so terrible it brought Nellie Bly on a secret mission of investigation. Her writing so exposed the horrors, it forced an historic change in practices nationwide.

Bly is honored in nearby Lighthouse Park with The Girl Puzzle, a large art installation by Amanda Matthews, opened in 2021.

Blackwell House: This is a historic house that was built in the 1790s. Now a museum, it was recently restored using public funds, guided by local historian Judith Berdy.

Bring Your Walking Shoes Because There’s So Much More

  • Lighthouse Park: This is a park that offers views of the Roosevelt Island Lighthouse and Hell Gate where the East and Harlem Rivers slug it out with tides from Long Island Sound. A good spot for picnics and relaxing.
  • Southpoint Park: Shore to shore views of the Manhattan skyline as well as fast-growing Long Island City. On the way to Four Freedoms.
The Smallpox Hospital, designed by James Renwick, in Southpoint Park.
  • Cornell Technion University: Commonly known as Cornell Tech, it’s an historic technology landmark. Its architecture in Phase One is groundbreaking in itself. And while the campus transformed Roosevelt Island, it also brought the city up to speed in leading edge technology.
  • The Girl Puzzle: This is a public art installation in Lighthouse Park. It consists of four statues of girls and is a tribute to pioneering journalist Nellie Bly.
Amanda Matthews’s The Girl Puzzle on opening day. In the background, the Roosevelt Island Lighthouse undergoes restoration.
  • The Chapel of the Good Shepherd: This is an historic chapel built in 1885. It is now a community center located in Roosevelt Island’s town center.
  • The Main Street Canyon: A pedestrian walkway stands as a reminder of Roosevelt Island’s original purpose, a one of a kind community that defied real estate interests by honoring people first.

Roosevelt Island Tour Guide Options

There are many other sights and attractions on Roosevelt Island, and a tour guide would likely tailor their tour to the interests of their customers. Roosevelt Island is a unique and fascinating place, and there is much to see and learn here.

And needless-to-say, the Island is loaded with places to eat — from the Café at Cornell Tech to Granny Annies in Riverwalk Commons to Nisi in the Main Street Canyon. Enjoy a full day, maybe as your own Roosevelt Island tour guide.

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