The best hour to eat near Union Square is the one most people skip: the stretch between leaving the office and sitting down to dinner. From about 2 to 6 on a weekday, a couple of the Italian rooms around the square run an early aperitivo window, the bar seats are open, and you can have a spritz and a few small plates without committing to a full meal or a reservation. If you have tickets to something at Irving Plaza later, or you 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 off 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, a few 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 open at 5 and take walk-ins at the bar, though 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. In summer the drink of the season is almost always a spritz of some kind, which is exactly what the early menus here lean on.

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 is large 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, and the bar menu is a short list of small bites and spritzes rather than the full dinner card: things like saffron arancini and a guanciale toast, with a rotating handful of spritzes and cocktails. Prices and pours change with the season, so check the current list before you build an evening around a specific drink. 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.

Tarallucci e Vino, East 18th Street

A block north of the square, 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 all day, 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 and will seat a walk-in at the bar, where you can order off the full menu without a reservation.

Rezdôra, on East 20th Street, is famously hard to book for a table, but the bar is a different proposition and a fine place to start a night with a glass of Lambrusco. Massara, a few blocks up at 913 Broadway, opens for dinner at 5 every night and cooks southern Italian; 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 you are willing to walk a few blocks north into Gramercy, the options widen. There is a full rundown of the exact happy-hour windows a few blocks north in Gramercy, which is worth a look when the Union Square rooms are full.

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 best part of the evening here, which is 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.