"We are pub trivia connoisseurs, going out once or twice a week for almost three years now.  As a result, we have high standards, and we always have a good time when Big Boy Trivia is running the show.  There are some really amateur trivia hosts out there in CT, but not Craig.  You can tell he has been doing this for years.  The questions are well done and creative, the game moves fast,  and you can always hear what is going on (which isn't the case with some other guys.) If you need something to do on a weeknight around New Haven, just go find a trivia night with Craig." - Scott M.

Trivia Nights

What Is a Big Boy Trivia Night? 

A Big Boy Trivia Night consists of 5 rounds of various categories designed to make you think, invite you to eat and drink, and enjoy a good night out with friends and family. Rounds are 10 questions each and the highest-scoring teams win cash and prizes (varies based on location).

Would you like us to host a private trivia event for a team-building day at the office, a school fundraiser or a different twist to a party or a rehearsal dinner? Contact us and we'll build an event for you!

Some of our past trivia rounds:

MATH  How many kids in each sitcom family?
NAME THAT TUNE  Spoken Word Edition
MOVIE QUOTES  That's What She Said

"Big Boy Entertainment & Craig, the owner, can be trusted to deliver for any wedding, party, etc.  He has made this business his priority and will go above & beyond to make his clients happy.  His trivia nights also can't be beat.  I've been to others that are much too long, poorly organized, or have questions that are so difficult, it takes all the fun out of the night." - Andrea T.

Are you a bar/restaurant owner
who wants to increase their weekly revenue?

How about a trivia night?

If your restaurant or bar is interested in hosting a trivia or karaoke night, Big Boy Entertainment can fulfill your needs and help grow your business. These events consistently increase your venue's attendance, especially on quieter nights.

Want us to host a private Trivia Event?

 We'll run it the same way we run one of our Weekly Trivia Nights,
but this one is just for you.

These events are GREAT for:

  • Business/Team-Building with your employees
  • Fundraisers
  • A twist on your rehearsal dinner
  • Birthday/Anniversary parties

A private trivia night is 2 hours and includes music between rounds and a professional host.


Trivia Registration starts at 8pm. Game begins at 8:30*(unless noted).


Woodbridge Social
12 Selden Street
Woodbridge, CT 06525


Jake's Tavern
179 Center St.
Wallingford, CT 06492

Eli's Orange
285 Boston Post Road.
Orange, CT 06477

Bar 140
140 Center Street
Shelton, CT 06484

Thimble Island Brewing Co.
16 Business Park Drive
Branford, CT 06405

Local Kitchen & Beer Bar
85 Mill Plain Road
Fairfield, CT 06824

Libetry Rock Tavern
229 Bridgeport Ave.
Milford, CT 06460


Local Kitchen & Beer Bar
68 Washington Street
South Norwalk, CT 06405


Bad Sons Brewing Co. 
251 Roosevelt Drive
Derby, CT 06418

No Worries Brewing Co. 
2520 Sate Street
Hamden, CT 06517

River Rock Tavern
5 Main Street
Derby, CT 06418

Sports Haven
600 Long Wharf Drive
New Haven, CT 06511


Question of the Week

October 23 - October 26, 2017

Who was the only MLB team to win 2 World Series titles in the 1980's?

Write the correct answer on your sign up sheet to get 10 Bonus Points.