New York City’s Upper East Side has long been on my ‘to visit’ list. On my most recent visit to New York, I was working which meant I had just one day to look around and see something new. But more importantly, I am partway through a re-watch of Gossip Girl * (original, obviously). This meant only one thing—I had to spend a day on the City’s Upper East Side.

I was told by many New Yorkers that the Upper East Side is “just residential” and not worth a visit. It’s true that apartment buildings dominate (and no, they’re not all shoeboxes). This area is so much more than a sleepy neighbourhood for Manhattan’s elite. Plus I find wandering suburbs or residential areas fascinating – the shops, cafes and people you meet help you really get a feel for a place.

I found just by taking the day and wandering, that the Upper East Side was a part of New York that had plenty to explore (and eat). Shopping here does not rival Soho’s eclectic charm or the status of Fifth Avenue. There are however many gems, and a GREAT branch of Old Navy (which I don’t think many Upper East Siders use, but I got a great black dress).

The quip in Gossip Girl* that Dan makes about the cost of coffee here versus Brooklyn is true. I somehow spent more of my hard-earned money than I thought possible on a bagel (yes I know inflation, but still… $20 for a bloody bagel!)

Most importantly, the Upper East Side is home to the best hot chocolate I’ve ever had—but more on that later.

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Where is the Upper East Side?

The Upper East Side is one of Manhattan’s most famous neighbourhoods, and as Gossip Girl *likes to remind us, it’s home to Manhattan’s elite.

The Upper East Side stretches from 59th to 96th Street. It is bordered by Central Park on the west and the East River (on the East, not surprisingly). It is home to some of New York’s most iconic cultural sites, from the Metropolitan Museum of Art to the Guggenheim. If you’re picturing brownstone buildings, immaculately kept tree-lined streets decorated with large boxes of flowers, and impeccably dressed residents, you’re on the right track.

Why should you visit the Upper East Side?

This combination of opulence, culture and wonderful eateries means that the Upper East Side is a great destination for anyone looking to experience a quieter, more refined side of New York. With Gossip Girl landmarks scattered throughout, it’s easy to feel like you will run into Serena or Blair at any time.

My logistics

I travelled to the Upper East Side by CitiBike (New York is surprisingly safe for cyclists – a tip from my colleagues based there) from the Millennium Hilton (which is not far from the bottom of the Upper East Side in midtown, near the UN).

I chose to cycle because: 1 I HATE the Subway (no really, it makes the Tube in London look clean) and 2 Well, I was being tight and didn’t want to pay for a cab. Plus the hotel had a deal with CitiBike, so it worked out well for me.

If you want a real Gossip Girl experience, there are a ton of tours on GetYourGuide (NB I’ve not done one so can’t vouch for them).*

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My Upper East Side Highlights

The Cooper Hewitt Museum

One hidden gem on the Upper East Side is the Cooper Hewitt, Smithsonian Design Museum, housed in the historic Andrew Carnegie Mansion. Fans of Gossip Girl might recognize it as the inspiration for the Constance Billard School for Girls, Blair Waldorf’s alma mater.

The museum itself is a treasure trove of design, with exhibitions that range from graphic arts to textiles and furniture. It’s an immersive space where you can engage with the artworks. There is also space to create your own digital designs. The architecture and interiors reminded me of a National Trust property in the UK.

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Possibly the best hot chocolate on the Upper East Side

One thing you absolutely cannot miss on the Upper East Side is Glace Hot Chocolate. It feels like the sort of place I should have hunted down from instagram, but in truth I just walked past it and couldn’t resist. The shop is tiny (most seats are on the pavement) but the hot chocolate will blow your mind. Thick, velvety, and made with rich, premium cocoa, it’s like drinking dessert. Each cup is topped with a dollop of homemade whipped cream and a sprinkle of cocoa powder.

The Met

No Gossip Girl-inspired day on the Upper East Side would be complete without a stop at The Metropolitan Museum of Art. Yes, the steps of the Met feel like the Gossip Girl hierarchy is a real thing. The Met however is much more than just a set of steps. Inside, you’ll find a world-class collection of art spanning over 5,000 years, from ancient Egyptian artifacts to Renaissance masterpieces and modern American works. The Met’s rooftop garden is another highlight, offering views of Central Park and the city skyline.

Central Park (and its Reservoir)

Of course, the day wouldn’t be complete without a stroll through Central Park. The Jacqueline Kennedy Onassis Reservoir, one of the park’s quieter spots, is just a short walk from the Met and offers an incredible view of the city skyline reflected in its still waters. The park itself is practically a character on Gossip Girl, and wandering its paths feels like walking into countless classic New York scenes. If you are lucky, you will also get to see budding actors or influencers capturing content (though they don’t seem to appreciate you staring at them when filming!)

The Church of Heavenly Rest

By the time I got to the Guggenheim I didn’t have the energy for a third art gallery (I know, shocking) so I opted to nip into the church next to it. What looked a little plain from the outside was stunning inside (my mediocre photo doesn’t do it justice). The carvings inside and stained glass windows really add to the atmosphere of the church.

*denotes an affiliate link, which means if you make a purchase I get a small commission at no cost to you.

Save the Upper East side for later