Aperitivo and after-work drinks near Union Square

The room a restaurant near Union Square is at four in the afternoon is not the room it becomes at eight, and the phrase “italian restaurant union square” promises the later version every time. From about 2 to 6 on a weekday, a couple of the rooms around the square run an early aperitivo window: bar seats open, a short menu, a spritz and a few plates without committing to a full dinner or a reservation. If you have tickets at Irving Plaza later, or just want to land somewhere before the dinner rush, this is the slot to use. Here is who actually runs an early window near the square, when, and where to go if you would rather sit at a bar and order the full menu.

At a glance

Two rooms within a short walk of Union Square run a real early window on weekdays. Isabelle’s Osteria, three blocks north on Park Avenue South at 20th Street, keeps an Aperitivo Hour from 2 to 6, Monday through Friday, at the bar. Tarallucci e Vino, a block off the square on East 18th Street, runs a happy hour from 3 to 6 in its bar and outdoor seating only. If you would rather skip the early menus and just start the evening at a bar, Rezdôra and Massara both start dinner at 5 and neither discounts. Everything here sits inside about a ten-minute walk of the square.

What aperitivo is doing near Union Square

Aperitivo is the Italian idea of a drink and a small bite before dinner, meant to open the appetite rather than replace the meal. It is not quite the American happy hour, even when the timing overlaps, and if that distinction matters to you there is a good piece on why aperitivo and happy hour are not the same thing. Near Union Square the practical version is simple: a spritz, a few plates, and a seat before the room fills up.

The rooms that run an early window

Isabelle’s Osteria, Park Avenue South at 20th

Isabelle’s has the bar built for this. The room seats 150 and the bar is long, so the early window rarely feels like fighting for a stool. The weekday Aperitivo Hour runs 2 to 6, Monday through Friday, at the bar, and the pricing is flat: $5 small bites, $5 spritzers, $5 cocktails, $5 wine, $5 beer. It suits the person who wants to arrive early on purpose, whether that is to eat lightly before a show or to hold a comfortable seat while the rest of the party is still on the train. When you are ready to see what the bar is pouring this month, explore Isabelle’s Aperitivo Hour and go from there. One thing to know before you plan around it: the restaurant does not publish daily opening and closing hours, so call (212) 388-1145 if your timing is tight.

Tarallucci e Vino, East 18th Street

A block north of the square at 15 East 18th Street, Tarallucci e Vino is an enoteca at heart, which makes it a natural aperitivo stop. Its happy hour runs 3 to 6 and is limited to the bar and the outdoor seating, so aim for a stool or a sidewalk table rather than the dining room if the early pricing is the point. Because the place is open from 8am on weekdays, it is also the low-stakes option: you can drift in at 4, have a glass and a snack, and decide whether you are staying for dinner once you see how the evening feels.

If you would rather just sit at a bar

Not every good early drink comes off a discount menu. Two of the more serious kitchens near the square open at 5, which is the hour with the most room at the bar and the least competition for it.

Rezdôra, on East 20th Street, is the one we would not count on without a reservation, but the first half hour of service is the least crowded it gets. Massara, a few blocks up at 913 Broadway, opens for dinner at 5 every night and cooks Campanian food; arriving right at open is the easiest way in. Neither runs a discounted window, so go for the room and the wine rather than the check.

If the drink is really a prelude to a full meal, the eight rooms around the square sorted by how late each kitchen runs picks up where this leaves off, and if the whole evening is built around a show, the pre-event timing guide sorts the same blocks by how many minutes you have. For the streets a little further north, where Italian dinner sits in Gramercy covers the corridor above 20th Street.

Frequently Asked Question

What time does aperitivo actually start near Union Square?

On weekdays, the earliest is Isabelle’s, whose Aperitivo Hour opens at 2 and runs to 6, Monday through Friday, at the bar. Tarallucci e Vino starts a little later, from 3 to 6, in its bar and outdoor seats. Both are weekday windows, so a Saturday plan needs a different approach: on weekends you are ordering off the regular menu at whatever time you sit down. If your goal is the early, lighter version with a spritz and a couple of plates, aim for a weekday between about 3 and 5, which is late enough that the kitchens are settled and early enough to beat the dinner crowd.

Where to start

If it is a weekday and you want the full early ritual, start at Isabelle’s bar around 3 and let it run. If you are near the square with less of a plan, Tarallucci is a block away and easy. And if the point is a good glass rather than a deal, walk into Rezdôra or Massara at 5 and take the bar. Any of them gets you the quiet hour before everyone else shows up.

Editor’s note: Isabelle’s Osteria is affiliated with this publication. Restaurants were selected using the criteria described above.