You met someone on OKCupid and their only interests are: bluegrass, craft cocktails, and spending time with their four-year old nephew. You've seen pictures of the nephew, and he looks dumb and boring, so you roll with the other two interests. Now you need a bar that has bluegrass.
If you’ve been in this situation, this guide’s for you. Also, if you like bars and you like live music, this guide is for you.
To be clear, this isn’t a list of venues. These are bars that happen to have live music. Even when there isn’t music, we still like to hang out at these places. True, we could have just called this guide “bars we like," but that wouldn’t have been very specific. Obviously, you know nothing about naming guides.
According to Google, a honky tonk is a “cheap or disreputable bar, club, or dance hall, typically where country music is played.” Yeah, that sounds like Skinny Dennis. This Williamsburg bar is cheap and disreputable in all the best ways. We suggest you lean on the bar, double fist some Lone Stars and chat with a friend while you catch some country music with your peripheral hearing. Most nights there’s a band - just check the calendar to see what’s coming up.
Manhattan Inn falls somewhere in between a bar, a restaurant, and a lounge, and somewhere in between divey and classy. You could eat a full meal there, but you could easily just camp at the bar and have a cocktail while you listen to whatever’s going on that night. There’s live music (on the grand piano, mostly), but they also do karaoke and dance parties. For dinner beforehand, try Cherry Point a block away.
Little Branch isn’t quite a speakeasy, but it also isn’t a normal bar. There’s no sign out front, there are a bunch of rules, it's in a basement, and the cocktails are excellent. That last part's why you go to Little Branch. It's in the West Village, and it can feel like a tourist trap at times, but if you go on a weeknight you can usually catch some live jazz and have a cocktail in relative peace.
The Flatiron Room takes its speakeasy shtick a little too seriously, but there's live music and a lot of whiskey. Sure, it can feel like you’re in the American Prohibition section of the Epcot Center, but that’s part of the fun. Music is typically jazz and blues, and it’s the perfect place to bring someone... mature (old).
Alphabet City is a neighborhood. The people there know each other, and they even seem to like each other. We suggest you head over, be friendly, and pretend you're a local at the the 11th Street Bar. It’s a dim little pub that has live music most nights. Sometimes it’s jazz, sometimes it’s folk, and sometimes you’ll get something else. It’s a toss up. Check the schedule. Also, eat at Babu Ji first.
Mona's is deeper into Alphabet City than 11th Street Bar, and even fewer tourists make it over. Maybe that’s why we like it so much. It isn’t the nicest bar in the world, but at the nicest bar in the world there’s probably a huge line for drinks. Not so at Mona’s. Mona’s is small, dive-y, and people seem to know one another. The house specialty is New Orleans jazz, but you can also hear bluegrass on Mondays.
St. Mazie345 Grand St
St. Mazie is an excellent date spot in Williamsburg. Bring someone you like, order at the bar, then listen (and maybe dance) to live flamenco. We can’t promise it’ll always be flamenco, but there’s some form of live music most nights around 10. The bar itself is dark and cozy, and there's an excellent patio. Should you get hungry, there's also a full restaurant in the basement.
The Dead Rabbit is probably the best drinking option available to all humans living or working in FiDi. The upstairs is upscale, and the downstairs is more laid back. Both spaces feel like a pub from the 1800's, and they both have music. Check the calendar to see what's playing, but usually it’s a pianist or some Irish folk music. Also, be sure to get a cocktail or a bowl of punch - because the bar game is top notch.
Most weeknights there’s jazz, mambo, or some kind of brass band situation at Apotheke. On weekends, you’ll probably hear a DJ (and you’ll probably have to get past a doorman). There’s a big seasonal cocktail list, and there’s also a prohibition cocktail list, because bars are still doing the prohibition thing. Go for upscale cocktails and throwback vibes in Chinatown.
Belly Bar used to be called The Leadbelly, and only the name has changed. You can still bring a first date here, and you can still hear live music on weeknights. The space itself is long and narrow and a lot more attractive than what most bars settle for. Have a cocktail or a beer and linger while a band plays. Stay for a late-night DJ set or head to a rowdier LES bar if you feel like making worse decisions.
People jam out at Bar Lunatico, and the musical styles are all over the place. Performances begin nightly at 8:30, and the kitchen serves small plates till 10. Get a cocktail with something weird in it and listen to whoever's playing that night. You might get dubstep, or it might be Brazilian pop. This place is small and cozy, and you never know what you're gonna hear. Be adventurous, don't check the schedule.