The Upper West Side has plenty of drinking options. There are cocktail bars with live music, lots and lots of sports bars, and wine bars with people on first, second, and fiftieth dates. There’s also a stretch of Amsterdam Avenue full of college bars, where you’ll find things like beer pong and people tapping on multiple car windows asking if this is their Uber. So no matter what type of place you’re looking for, use this guide the next time you go out on the Upper West Side.
Vanguard is one of the best first-date spots on the Upper West Side. It’s a big French wine bar, and even on weeknights it gets pretty full of couples talking about their siblings and where they went to college. That said, it’s equally good for a drink with a few coworkers, or a catch-up with a friend. Just be aware that the whole place might smell like truffles, since they serve various truffle- and non-truffle-related snacks.
E’s Bar is one of our go-to spots in the neighborhood, because they do so many things right. There’s solid bar food, you can get a good cocktail, and the space feels kind of like a long clubhouse with booths, darts, and board games. It’s a great spot for a big group hang, and if you live in the area, you’ll probably wind up knowing at least one bartender by name.
We don’t mean this as an insult to the land above 59th Street, but The Owl’s Tail is the sort of place you expect to find downtown. It’s a little spot decorated like a living room in a very nice apartment, and they serve top-notch cocktails. You can drink one at the L-shaped bar in the corner, or you can grab a little table along the wall. Bring a date or meet some friends here, and if anyone gets hungry, get a few small plates like meat, cheese, and oysters.
Prohibition has live music every night, so it’s a good option for all kinds of situations, from first dates when you want to avoid awkward small talk to quick solo drinks when you’re killing time. Get some house cocktails at the bar, and if you end up wanting a break from the music (or you come before the music starts), hang out at one of the sidewalk tables out front.
As we mentioned, the UWS has no shortage of sports bars - but Blondies is our favorite. This place gets packed during big weeknight games and all day on weekends, with the booths and tables in the dining room usually reserved days in advance. That room and the first-come first-served bar area both have lots of TVs playing games at high volume, but what really sets Blondies apart from other sports bars is the food. Particularly the buffalo wings, which are some of the best in the city.
Caledonia is, above all, a whiskey bar. They have an enormous scotch selection, a large number of snifters, and plenty of Irish and American whiskey as well. That said, it isn’t the sort of place where you have to whisper and swirl your glass before you take a drink. Mostly, it just feels like a relatively calm pub that happens to have a lot of brown liquid in stock. The little space is long and narrow, with a bar up front and a few tables in back, and it works for anything from date night to a drink with your parents.
You’re on the Upper West Side, and you want to drink beer. But not a beer that all your friends have heard of. You want something obscure, because your horoscope recently told you to try new things. Go to George Keeley. From the outside, this place looks like a very normal pub - and on the inside it looks pretty normal, too. What sets it apart is the fact that there are so many hard-to-find beers on tap. Big flat-screen TVs behind the bar show lists of what they’re currently pouring - and there are also a few other TVs for watching sports.
There are a few things that differentiate Bodega 88 from the other sports bars in the neighborhood. First of all, the TV situation here is pretty great - each booth has its own screen, and then there are multiple big screens over the bar. Secondly, the food is more exciting than what you’ll find at other spots nearby (the fries come with chimichurri and manchego cheese, and the fried calamari is glazed with Dominican honey). The space is about the size of a studio apartment, so we wouldn’t recommend bringing a group, but it’s a decent place to watch sports alone or with a friend, especially before 7pm when drinks are half off.
Whether you have opinions on mosaic versus cascade hops or you don’t know IBUs from IPAs, check out Gebhard’s. They have a bunch of beers on tap that you definitely won’t find on the shelves at Whole Foods, and the dark space works well for a low-key drink with a couple friends. If you don’t feel like staring into pint glasses and wondering about fermentation processes, you can play darts or foosball instead.
The Dead Poet is really just a solid neighborhood bar. Isn’t the least bit fancy, but it also doesn’t smell bad, and they even have some books you can read while you drink. There’s one long room with a couple of TVs for watching sports, and you’ll also find both daytime and late-night Happy Hours. The whole space is about the size of a subway car, though, so don’t bring a big group.
You want to watch sports with some friends, and maybe share a couple pitchers of beer - ideally something other than Hoegaarden or Goose Island. Get a table or some bar seats at Dive Bar, a dimly-lit spot with over 30 beers on tap (most of which are available by the glass, growler, and pitcher). Once the Jets are down by 24 and you want to focus on something else, start working your way through the huge menu of bar food.
Walk into this wine bar and you’ll see some tables, a few bar seats, and a big wall stacked with French wines, over 40 of which are available by the glass. This is an excellent spot for a first or second date - especially if you meet on the early side, since wines are discounted during Happy Hour (until 7pm).
Despite the name, Dive 75 isn’t actually that divey. Sure, it isn’t the fanciest bar in the world, and if you order a sazerac here, you might get a weird look - but it’s a nice little place to hang out with a beer, and there’s a sitting area in the back with a couch and some armchairs. There’s also a big stack of board games in one corner, and, with its giant fish tank and mismatched wall decor, the space feels almost exactly like the common area of an off-campus house where six college seniors live.
Like the other locations of Vin Sur Vingt around the city, this UWS outpost is a good spot for a quiet drink with one other person or a small group. It’s a small, brick-walled wine bar where you can also get some snacks, like tartines and shareable charcuterie plates. Plus, the long, all-French wine list has over 50 options available by the glass, and you can even try things in flights of three or five glasses.
If you’re with a few friends near the northern end of the Upper West Side, and you’re looking for a very normal bar where you can hang out for any length of time while you have some inexpensive drinks, go to Bob’s Your Uncle. It feels sort of like a big, slightly divey rec room, with brick walls, a shuffleboard table, and photos of various people named Bob up on the wall. They also have jello shots, so your night here can either be very tame or full of colorful, gelatinous alcohol.
Amsterdam Ale House plays sports on a few TVs, but it feels less like a sports bar and more like a casual neighborhood spot than any other place on this stretch of Amsterdam Ave. They have over 30 beers on tap, many of which are unusual options from relatively small domestic and international breweries, and the space tends to fill up with big groups drinking and sharing bar food. You can get food here until 2am, so keep this place in mind for drinks and a bite after a show at the Beacon Theatre a block away.
This seasonal (May-October) outdoor bar has a bunch of umbrella-covered tables that might make you think you’re in Madison Square Park, except for the fact that you can see the Hudson River and New Jersey. It’s a good spot to day drink with a big group, but there’s no table service - you’ll be notified by a buzzer when your order is ready at the counter.
St. James Gate is very much an Irish pub, but not in a cheesy kind of way. It’s a good spot to eat some bangers and mash, and it’s perfect for when you want to sit on a barstool and watch sports with a Guinness. The big open room is filled with tables, and the service is about as friendly as we imagine it would be in a neighborhood pub in Ireland.
The next time you’re feeling nostalgic about your college days, you could build your own beer pong table and throw out your couch to make room for it - or you could go to Jake’s Dilemma. This big bar on Amsterdam Ave feels like the kind of place you might have gone junior year, complete with foosball, pool tables, and, yes, intense games of beer pong. If you want to pay college prices for that pitcher of Shock Top, come during Happy Hour (until 8pm every day).
The Gin Mill is owned by the same people as Jake’s Dilemma, which is less than a block away, and it feels very similar. Come here when you want to watch college or NFL football, and bet pitchers of light beer on the outcomes of beer pong games with friends. This place also does Happy Hour deals every day until 8pm, including half off the whole bar on weekdays and half off beers on weekends.
We aren’t quite sure what Dakota Bar is trying to be, but it’s a useful place to know about if you ever need to get a cocktail with some acquaintances near Lincoln Center. It’s about equal parts bar, restaurant, and lounge - and it looks sort of like a place where lawyers would hang out on a Friday night in a ’90s sitcom. There’s a bar in the middle of the room, some banquette seating, and a few tables - plus floor-to-ceiling windows looking out on 72nd Street. Bring a few relatives you haven’t seen in a while.