In Search Of CT’s Best Trivia Night

In Search Of CT’s Best Trivia Night
10 comments, 04/25/2014, by , in ENTERTAINMENT, LOCAL

It started simply enough.

A phone call from my pal, asking me if I’d be down for trivia with some other friends & co-workers at Plan B. Burger in Milford.

Considering that I live in SoNo, and that I hate driving pretty much anywhere, I was quickly wracking my brain for excuses not to go. And that’s when he hit me with the question that quickly made the decision for me.

“C’mon. When’s the last time you’ve ever actually won ANYTHING?”

And the truth is, I couldn’t even remember. I dunno, maybe like $100 on a scratch ticket like five years ago? A few random hands of poker here n’ there?

Regardless, it kind of lit a fire under my ass- and just like that, that simple question motivated me enough to make the half hour drive up 95 to Plan B.

Almost immediately after I arrived as the fifth member of our team (“Meghan’s New Hair Color”-to honor the new ‘do of one of our teammates) I remembered that even though I don’t consider myself a trivia junkie by any means, I love the ritual of trivia night.

It had been years since I’d participated in a trivia night on a regular basis, but now I think I need one back in my life again. And as I sat at my table sipping my cheap-ass Narragansett draft, I began to wonder: what is it about this little competition that I’ve always loved so much? Why do I and others like racking our brains and resurrecting useless knowledge and information? And furthermore, considering how mobbed the joint was on a random Thursday night, why do we participate in trivia competitions as a social ritual?

Well, despite my friend’s lust for winning, I generally think that the draw of Trivia Night is that the expectations and risks are low, thus the reason so many people participate. Plus, it’s always a good time sucking down some wings and beers while bullshitting with your friends, right?

Now with all that being said, I’m proud to announce that “Meghan’s New Hair Color” tore shit up last night, rallying from 5th place with just two rounds to go, to winning the whole damn Trivia Night.

And it was awesome.

High fives, yelling, that temporary feeling of being not only drunk-but also drunk with power.

Speaking on behalf of my teammates, I think they’d all agree that it was pretty invigorating all-around.

The problem is (and this is no offense to Plan B. Burgers, who are great) is that for all of our trivia savvy, and knack for the comeback, all we won besides the bragging rights was a $20.00 gift card.

This is bullshit.

We, the representatives of “Meghan’s New Hair Color” demand all the riches. We want half of our bill paid, or at least a $50.00 gift card. In other words, give us a reason to keep coming back to your Trivia Night, because a mere $20 gift card isn’t going to cut it.

So this is where you, the fine CTBoom reader come in.

I’d like you to please leave some Trivia Night recommendations below. Preferably for Thursday nights, but we’re really not that picky. We’d just to know where it’s hot, where the questions have a good level of difficulty, and most importantly, who’s got the biggest payoff.

Do please let us know, and be forewarned. “Meghan’s New Hair Color” might be knockin’ on the door of one of those nights you’ve recommended.

About Murray

is a writer for CTBOOM


  1. amygrey1041
    April 30th, 2014 15:11

    Wilson’s Pub in Collinsville!! Every Tuesday night! The vibe is sick!


  2. Liz
    April 26th, 2014 16:51

    WhatTrivia is the BEST in CT  - especially at Billy Tee’s in Cromwell on Thursday night.  It is FREE bar trivia, there’s no fee to enter, and as such, I consider the $ 50/25/10 gift cards for the top three teams to be quite generous.  The food is fantastic and you won’t have to suck down swill like cheap-ass ‘gansett – there are 19 decent beers on tap, and plenty of other tasty concoctions to tempt your palate.


  3. Shane Carty
    April 26th, 2014 15:13

    Anna Liffey’s longest running in the state, every Tuesday night


  4. BeckyLeutertDurant
    April 26th, 2014 13:57

    Whattrivia at Billy T’s on Thursday nights in cromwell. if you want another night, try Tuesdays at Arch street in Hartford or Wednesday at Damon’s Tavern. awesome trivia, great regulars (of which I am one).


  5. April 26th, 2014 10:10

    WhatTrivia is a local company that has a couple nights around Hartford.  We give out gift cards to the restaurants we run trivia in:
    Arch St. Tavern in Hartford Tuesday at 7pm – $50 for first, $25 for 2nd, and $12.50 for 3rd place.
    Damons Tavern in Hartford Wednesday at 8pm – $30 for first, $20 for 2nd, and $10 for 3rd place.
    Billy Tees in Cromwell Thursday at 8pm – $50 for first, $15 for 2nd, $10 for 3rd place.

    All the questions are “figure-out-able” meaning there’s no “When was the first battle of this obscure war?” but it’s not easy either.  We do a photo round, involve wagering so there’s an art to it, and usually have every place packed each night.


  6. April 26th, 2014 0:27

    Whats good? The Great Doc P here! I work with Big Boy Trivia! Thursday Night we have an awesome night at Maddens Gastropub in New Haven 175 Humprey St. Grand Prize is a $50 Gift Card. Sign up is 8pm game starts at 8:30PM. I also host Monday nights at Whiskeys in Derby!! Come see me!


  7. Ken3
    April 25th, 2014 22:16

    Bufflo wild wings every wen night at 7 pm in Southington . They don’t hand out $$$ but free shirts/ hats and other cool things just for playing. Last week for first place they have out RedSox tickets


  8. TraciSchneider
    April 25th, 2014 22:14

    You have to check out DJ Trivia!  Top 3 teams for the night get gift cards to the location they play at. They also have trivia leagues the best teams go to play offs and then if your good enough, grand championships for a sweet cash prize. There are many locations to choose from.  Here is the website: and the facebook page:


  9. Dark anjel
    April 25th, 2014 19:42

    We run a really fun and interactive trivia night on Thursday’s at Yama Dora Asian Grill in East Haven. We have video rounds….don’t forget the lyrics….lots of fun stuff and first place wins a $50.00 gift card to the restaurant. The best team name of the night also wins a free round of shots for their team. Come check it out sometime.


  10. Craig the Trivia Guy
    April 25th, 2014 19:19

    Check out any of Big Boy Trivia’s Nights! 1st prize ranges from a $50 Gift Card to $75 Cash. And all of their nights are FREE to play! Check us out at


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