Best Spots for a Spontaneous Evening in NYC

Our favorite way to experience a night out in a city is to pick a neighborhood and be open to where the evening takes you.

Some of the most memorable nights are not fully planned, but allow flexibility. In a place like New York City, this can also make things quite expensive if you don’t pay attention. But, despite the rising cost of cultural events in NYC, there are still a number of spots to have a carefree spontaneous evening.

Here are some of our favorites:


  • This legendary Park Slope establishment hosts some of the most talented Jazz, Funk, Afro-Carribean, and Eastern European musicians in the city. If you feel like it’s time to get out of your musical rut and explore a different genre, come here.  No need to purchase tickets in advance. Just put $10 in the bucket once you enter the back room and enjoy the musical adventure.


  • This Red Hook bar hosts the best bluegrass jam sessions in the city. Every night, people flock from far and wide to see musicians of all ages play sing-along bluegrass tunes. No ticket needed, just grab a cheap beer and find a seat where you can. It’s no longer the secret neighborhood spot it used to be, but it’s still a gem.

Mercury Lounge

  • Located close to other small music spots in Manhattan like Piano’s, Rockwood Music Hall, and Bower Electric, this is my favorite for the lot. Mercury Lounge hosts some of the best up and coming bands around the country. Tickets are usually $10-$15, and it’s the best place in the city to find a music group right before they hit the “big time”

Union Hall

  • Union Hall curates some of the best comedy nights in the city. The former stomping of renowned comic Mike Birbiglia, this venue puts on affordable, amazing lineups that will be sure to keep you laughing through the night.

Pete’s Candy Shop

  • The volume of art events happening at Pete’s Candy Shop is staggering. They host about 3-4 artists in their small, but charming back room every night. Whether it’s an open mic, comedy showcase, or a singer-songwriter, all of the events here are free, intimate, and don’t require advanced purchase.

What are your favorite spots that we’re missing from the list? What are your favorite spontaneous spots for a night out in your city?