Dining in Central Park truly couldn’t get any more “New York”
than at the Tavern on the Green, which has been a dinnertime
destination since the 30s. Originally a barn for the park’s sheep
that would spend their time in Sheep’s Meadow (hence the Tavern’s
logo), the restaurant spills out into the park and was recently
renovated, with wooden beams and pistachio-hued couches punctuating
the space, as well as a circular bar surrounded by leather stools.
For a classic experience, book a table during the holiday brunch – an annual tradition
among many people born and bred in the city – and toast to the
season with mimosas, roasted figs with goat cheese and honey, and
maple bacon. Warning: the spiced eggnog crème brûlée with
gingerbread cookies might also be difficult to avoid.

A pilgrimage that the beau monde of Westchester and Connecticut have made for
generations, visiting JG Melon is a tradition that has never lost
its charm. A bustling, energetic restaurant that does simple dishes
right (read: the best burgers in the city), this
is a no-reservations spot where you people-watch with a gin and
tonic at the bar before being led to your table. JG Melon has a few
locations, but the Upper East Side spot is as classic as it gets,
with publishing moguls keeping it low-key and Harvard rowers
jostling for space. If you’re sick of gourmet grilled cheeses
overloaded with caramelised onions, or just want a simple plate of
cottage fries, head here for the real deal.

A centerpiece of old-school New York, the bar at The Carlyle
hotel, with gold-tinged murals painted by the author of the
Madeline series, Ludwig Bemelmans, this spot is a go-to for a
cocktail to kick off a special night out. There’s a live pianist,
naturally, and the crowd ranges from fashionistas visiting town to
chic local couples enjoying a night out. The fleur du paradis
cocktail is exquisite (and comes with a matching price tag) while
the mini burgers make a great after-work bite.

In a city chock-a-block with old-time Italian restaurants, it’s hard
to distinguish the authentic from the try-hard. Unlike most of the
packed eateries in Little Italy, however, the Upper East Side’s
Isle of Capri is as real as it gets, continuously operated by the
Lamanna family since the 50s. Come here for classic dishes done
perfectly, such as the homemade lasagna, as well as the old-school
hosts who will ensure you’re taken care of. Don’t be surprised if
Robert De Niro is your dining
neighbour.

It’s not often that you’ll see someone stroll into a restaurant
wearing an actual top hat these days, but that just so happens to
be the type of thing that occurs at this Upper East Side eatery. While
the restaurant only opened in 2012, it possesses the feeling of a
place that’s been around for decades. Local families regularly
return for celebrations here, thanks to the highly attentive staff
headed up by a husband-and-wife team, the pan-roasted duck that
will transport you straight to Provence (ordered from a
hand-scrawled menu) and a crowd that has clearly lived in the city
forever.