Starting at 7:30pm every Monday Night NYC Trivia League hosts trivia at The Winslow Gin House and Eatery. Trivia buffs in the East Village and Gramercy neighborhoods flock every week to mentally flex on other teams. Speaking of trivia buffs, Bunny Massacre, a local trivia team and regular winners at The Winslow, were mentioned in this New York Times article referencing their devoted process to staying trivia savvy.



Do you want to become famous for how good you are at trivia? Do you ever wonder how much random knowledge you have stored in your brain? Would you like to document it as well as lord your superiority over your friends and strangers? If so, Pub Trivia night with NYC Trivia League at the Winslow might be the spot for you.
Every Monday at 7:30pm (right after Happy Hour) is your chance to come in with your friends and go head to head with other teams vying for both pride and prizes. If you are interested you can register your team here.
NYC Trivia League has over 75 participating bars in their network. Teams compete in a season format against not only other teams in this network of bars, but also teams competing from their home venue.
Things To Know About Trivia Night at The Winslow

Sure, trivia nights can be a dime a dozen, but this local haunt boasts an amazing time along with many prizes and specials that are anything but trivial. Many a factoid and alcohol enthusiast alike come every week to The Winslow to stretch their mind muscles as well as chase away any remaining case of the Mondays. Obscure facts: check. Drink Specials: check. The feeling of pride that swells within you when you know more than the person sitting next to you: check. Here are some other fun facts you should know about trivia at the Winslow hosted by NYC Trivia League:
- It’s Absolutely Free
It’s absolutely free to participate and the winning team also gets a $50 Winslow gift certificate to use at a future date (think delicious brunch Gramercy where you can watch NFL games and sip mimosas for hours, or maybe keep it for a future trivia night). A round of shots also goes to the 2nd place team as well as to the team with the best name. Hint, hint, the trivia host tends to favor the deep cut puns so don’t be afraid to go for the groan.
- The Rules are Simple
The rules are easy to follow, as well as the understanding there is an honor code amongst players:
- No cell phones
- No Shazam
- No Google
- No Bing
- No search engines of any kind
- Just don’t look things up. Use your brain.
- If we catch you cheating, you will be disqualified
- Don’t shout out the answer. It’s free to play, so why not grab an answer sheet from your trivia host? Please just keep the answers to yourself.
- Your trivia host has the final say.

- Recommended Team Size
NYC Trivia league recommends six players per team. Six or fewer people on a team is great, but if you have more than that you can split up your team into two teams and make it a battle royale. Winning against strangers is fun, but beating your buddies gets you bragging rights.
- Point System
Categories of each round range greatly in subject matter and there is no betting or wagering allowed (save that for your Fantasy Football draft party). Most trivia nights do include a music or picture round.
There is a possible total of 50 points broken down as follows:
- There are five rounds of trivia
- There are 10 question per round
- Each question is worth one point
- League Rules
Find more information on NYC Trivia League and their league rules here.
Pub trivia is great because it covers so many bases. If you’re bringing a group make sure you have “experts” who have general knowledge in pop culture, geography, botany, cobbling, chemistry, geology, Six Nations Rugby, history, literature, etc. You know, the hits.
If social anxiety is more your speed, and you hate chatting at bars, NYC Trivia League at The Winslow might help ease that stress. Think about it, it’s a bar activity that everyone can participate in, yet avoid all the small talk. The devil is in the details.
Monday Trivia Night at the Winslow always has drink specials as well as an amazing food and cocktail selection. Grab your thirst, grab your knowledge, grab yourself, grab your friends, then head over to The Winslow on Monday nights and grab a table. No seriously, seating is limited and tables are first come first serve so be there promptly by 7:30pm and let your brain and NYC Trivia League take it from there.