Top Things to Do and See on the Upper East Side

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.
Once you’ve explored the area make sure you book a stay at one of the best hotels on the Upper East Side through Culture Trip.

Olga Belykh contributed additional reporting to this article.