The Tipsy

Have Drinks With the Ghosts of Christmas Past at Pete’s Tavern

The Gramercy Park bar and restaurant has been inspiring writers, poets, Frank Sinatra, and the just plain thirsty for 154 years.

Photo by Sayaka Ueno

Pete’s Tavern is the kind of place that, as part of its special New Year’s Eve menu, includes a full breakfast served at 1:45. In the morning. It’s the kind of place that provided O. Henry with enough comfort and whiskey for him to crank out the mythic fable of empathy The Gift of the Magi, among other hit stories. The kind of place where, on a recent Wednesday evening, a visitor could enter through the grand, creaky, welcoming, wood-and-glass doorway, est. 1864; pass under a ceiling so packed with red Christmas lights that faces in the crowded front room glowed with cherry cheer; then walk across the tiled floor to a third room in the back, where a thick and wry waiter wearing the Pete’s uniform—pressed, white, button-down shirt and daisy yellow necktie—and leaning against a brick wall that looks like it’s been there from the beginning, would greet the weary traveler with, “You look like you have something on your mind—anything I can get you to help?”

Drink Tipsy History Pete's Tavern NYC
Winter is here. / Photo by Sayaka Ueno

Pete’s Tavern is not just the kind of place where all that is true—it is that place. Built on the same corner a block from Gramercy Park, where it remains today, it’s a martini-and-chop shop low on pretension, high on Old New York charm. Along with a couple other spots in town—McSorley’s, say, and the Ear Inn—it can legitimately make the case that it’s one of the oldest booze houses in town. The substantial wood booths that wouldn’t look out of place in a Victorian cathedral drive the point home deeper. (The framed celeb shots, meanwhile, evoke a different era; I sat under Tom Selleck, Bobby Cannavale, Daniel Radcliffe, and Adam Sandler.)

Built on the same corner a block from Gramercy Park, where it remains today, it’s a martini-and-chop shop low on pretension, high on Old New York charm.

When you go—and for reasons that will become clear soon, it’s recommended you go during the holiday season—one correct answer to that waiterly question is: Yes, sir, I’ll have one of your finest maple bourbon old-fashioneds, please. This drink is on the winter cocktail list, and if you must diverge from the classic beverages Pete’s will inspire you to drink, it’s not a bad way to go. This old-fashioned comes winterized with a substantial twig of cinnamon stick, which gives the familiar sweet twang a nutty undercurrent.

Drink Tipsy History Pete's Tavern NYC
Get cozy with Pete’s take on an old-fashioned. / Photo by Sayaka Ueno

Once your drink arrives, you are free to take in the scene around you. And it’s a scene so lively and true to New York, that Pete’s, for all the bear-hugging bonhomie of the guests that recent evening, is actually a great place to be alone. Especially in December. That’s when the decorations go up. And up and up and up. One long wall of the place is so dense with bright bells, mini Santas, and cotton-ball snow, it is possible to miss the massive faux sharks and other long sea creatures sharing brick with St. Nick.

Drink Tipsy History Pete's Tavern NYC
The view from our writer’s table. / Photo by Sayaka Ueno

This view is occasionally interrupted by the zipping masses in yellow ties. Waiters, busboys, and hosts race the tile balancing burgers, pints, and steak frites on wide silver discs, somehow avoiding a five-tray pileup. Keep your ears perked as they pass and you’ll likely catch a sliver of gold. I was lucky enough to hear two waiters cluck about how a younger staffer didn’t get their Wall Street reference. Imagine!

That Oliver Stone film on the goodness of greed came out in 1987, and the waitstaff banter underscored how Pete’s provides a portal to the mid-’80s. It’s a spot that makes you want to have a two-martini lunch. Or linger a while, nursing the house-made 1864 ale and watching busy city walkers skid past the tall windows while ignoring your iPhone. To concoct an indie film that could actually get a theatrical release. Yeah, that’s how mid-’80s the vibe can feel.

Pete’s provides a portal to the mid-’80s. It’s a spot that makes you want to have a two-martini lunch.

But it was on my way out that Wednesday night that I caught a glimpse of what might serve best as the tavern’s unofficial crest. There on a corner slab of wall near the kitchen and at the top of the steps leading to the basement bathrooms was a photo of Frank Sinatra. This fact alone may not shock you. Sinatra has one of the most captured faces of all time, and you’d surely struggle to find a New York establishment founded before 1999 that didn’t feature him in one way or another. But this photo is different. For one thing, he’s not wearing a tux or even a suit and tie. Instead, it’s Leisure Frank in an open-neck shirt and a cardigan. And there’s his gaze. His eyes are cast downward, away from the camera. The expression is contemplative, weary, lost, and lonely. You can’t even really see his most famous asset: those ol’ blue eyes.

Drink Tipsy History Pete's Tavern NYC
Ol’ downcast eyes. / Photo by Mac Montandon

In this photo, Sinatra is 65 years old. He looks like he could use some company. Companionship. A well-made drink and a joke. Or even just somewhere warm to sit a minute and collect his thoughts. We know just the place.

Need a bar recommendation near you? Find expert picks in every neighborhood on our app!