Top Things to Do and See on the Upper East Side

Photo of Anne Bauso
26 August 2021

Live the life of a true Manhattanite while strolling through the upscale Upper East Side for the day. This New York neighborhood is home to the world-famous Museum Mile, as well as a hodgepodge of retro eateries, brownstone apartment blocks and auction houses.

Filled with elegant residential streets, designer shopping and world-class cultural institutions, the Upper East Side is one of Manhattan‘s most desired neighborhoods – and that’s before you factor in next-door adjacency to Central Park, the city’s gigantic green space of grassy meadows, woodlands and serene waterways. Discover our recommendations of the best things to do when you’re next on the Upper East Side.

Ride the Roosevelt Island Tramway

Architectural Landmark
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The famous Roosevelt Island Tramway that spans the East River and connects Roosevelt Island to the Upper East Side of Manhattan
© Leonard Zhukovsky / Alamy Stock Photo
The Roosevelt Island Tramway is the best few bucks you’ll spend in New York City. For the cost of a subway swipe – two for return trips – this cherry-red sky tram skirts high above the East River, treating you to incredible views all around, including Brooklyn, Queens and the iconic Lower Manhattan skyline. The journey between the Upper East Side and Roosevelt Island takes about five minutes, with trams departing every 15 minutes.

Get down on one knee at Bethesda Terrace and Fountain

Museum, Park
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Bethesda Fountain with people view from the terrace in Central Park in a sunny day in New York
© Astes / Alamy Stock Photo
When Central Park co-designer Calvert Vaux dreamed up the Italianesque Bethesda Terrace and Fountain, he used the idea of love as inspiration. More than 150 years later, the theme lives on as it’s among the top proposal spots in the city. Today, you can stand on the terrace’s upper level and admire views — largely unchanged since the 19th century — of the Ramble, Central Park’s 36 forested acres (15ha). Go below to see the beautiful arched mosaic-tiled ceiling of the passageway.

Visit a World-Famous Art Gallery on Museum Mile

Museum
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Metropolitan Museum of Art, New York. The Charles Engelhard Court at The Metropolitan Museum of Art, 5th Avenue, Manhattan, New York City, NY, USA
© Ian Dagnall / Alamy Stock Photo
The Upper East Side’s famous Museum Mile contains several of the world’s most preeminent art museums in a single stretch. It kicks off in the south with the Metropolitan Museum of Art, a Beaux Arts behemoth housing everything from an ancient Egyptian temple to Issey Miyake couture. The trail runs north along Fifth Avenue connecting other major cultural institutions, like the Guggenheim and the Jewish Museum.

Go Climbing at Steep Rock Bouldering

Gym, Shop, Sports Center
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Exploring big cities means great exercise for your legs, but rarely do travelers get to work on their upper body strength. With two uptown locations, Steep Rock Bouldering is a meticulously clean bouldering facility that offers plenty of kid- and beginner-friendly climbing routes as well as ample space to move around – even when the after-school crowd departs. Day passes are available, with climbing shoes and powdered chalk to rent.

Treat Yourself at Lexington Candy Shop

Diner, Ice Cream Parlour, Candy Store, American, $$$
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Lexington Candy Shop on the Upper East Side, New York City.
© Elizabeth Holmes / Alamy Stock Photo
Everything at Lexington Candy Shop is made the old-fashioned way from scratch — from the soda to the malted milkshakes. Owned by the same family since it opened in 1925, this retro luncheonette captures New York of the past – with original menus framed on the wall next to vintage posters and photos. Some of the house favorites include their sweet lemonade and strawberry pancakes.

Sip a Cocktail at the Iris and B Gerald Cantor Roof Garden

Bar, Cafe, American, $$$
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This is one of New York’s greatest two-in-one attractions. Not only is the Metropolitan Museum of Art the city’s most revered art museum, but the seasonal Iris and B Gerald Cantor Roof Garden is a truly unique rooftop bar. It offers unrivaled, panoramic views of Central Park and the Manhattan skyline. On warmer days, snag a highly coveted spot under the shady trellis with a cocktail and snacks. The space is especially magical at sunset, when the sky turns pink behind the Dakota apartment building.

Grab a Coffee at Café Sabarsky

Cafe, Restaurant, Austrian, $$$
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Find out just how luxurious drinking coffee can be at this old world Viennese cafe with handsome wood walls and herringbone floors. Each European-style cup of coffee is a precious delivery to the marble cafe tables, especially when paired with an elegant slice of Sachertorte or buttery apple strudel. For more savory fare, there are Viennese classics like sausages, goulash and spaetzle for you to enjoy.

Hike Along the East River Greenway

Park
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The East River Greenway is an epic 9.4mi (15km)-long paved trail stretching from the southern tip of Manhattan to East 125th Street in Harlem. You can walk, run or bike the entire length in both directions. The southern leg offers top views of the Manhattan and Brooklyn bridges as well as the Brooklyn skyline – where the quieter northern portion of the trail edges the Upper East Side – keep your eyes peeled for Roosevelt Island.

Peek Inside Gracie Mansion

Building, Park
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Entrance to Carl Schurz Park, Gracie Mansion, Upper East Side, Manhattan, New York City
© Wendy Connett / Alamy Stock Photo
This city landmark has seen a lot of New York City life. Built as a country home in 1799 – on what was then the outskirts of NYC – it has since served as a park snack stand, a museum and a home to nine of the city’s mayors. One of the oldest surviving wood structures in Manhattan, the buttercup yellow Federal-style mansion lives on as a member of New York’s Historic House Trust. Public tours through the art-filled interiors are generally available twice a month, advance booking required.

Join an Auction at Sotheby's

Building
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Bidding under way on a Chagall painting, Sotheby's fine art auction, New York, New York, USA
© Philip Scalia / Alamy Stock Photo
You may not be aware of this, but visitors are welcome to walk into this world-renowned art broker’s showroom and check out the soon-to-be-auctioned items – free of charge. Expect to spy paintings, furniture, jewels, rare wine and other museum-ready merchandise. If you time it right, you can even sit in on an actual auction amid the couture-clad buyers and collectors – and bear witness to heated bidding wars and potentially astronomical sales.

Olga Belykh contributed additional reporting to this article.

These recommendations were updated on August 26, 2021 to keep your travel plans fresh.

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