5 Boston-area trivia nights you need to check out

A quizmaster explains some of the qualities that help make a trivia bar great.

Indie trivia at Aeronaut Brewing.
Indie trivia at Aeronaut Brewing. –Aeronaut Brewing

When seeking out trivia night in the Boston area, there are multiple factors that can determine whether you keep coming back. According to quizmaster Wes Hazard, the host of WGBH’s nationally syndicated TV show “Stories from the Stage” and a host for the quiz company Big Quiz Thing, good questions and good hosts are both keys to making a trivia evening entertaining.

Hazard, who won a little more than $53,000 as a contestant on “Jeopardy!” last year, said he’s more than happy to play trivia in his apartment by himself, calling a stack of Trivial Pursuit cards “a good night for me.” But as a host, Hazard said you need to give an audience more than that.


“A lot of what makes a good host is realizing that trivia night, for whatever else it is, is a night of entertainment,” Hazard said. “These are people who have chosen to spend some time with you. They could be at a concert, a literary reading, a comedy show, or sitting at home. You have to realize people have taken the time to be there, and you’ve gotta give them a show.”

Big Quiz Thing, which still occasionally visits the Oberon in Cambridge, makes use of video and audio rounds, and features questions that are both fun and clever, by Hazard’s estimation.

“I had a friend once who went to random bar trivia, and he got the question, ‘What is the length of the Queen Mary II ocean liner?’” Hazard said. “That is a horrible question! One, no one is going to know that, so you just alienated 99.9 percent of the people playing. And also, it’s uninteresting. Who cares? That question is not fun.

That’s why I really like Big Quiz Thing, for surrounding questions with a lot of cool video, cool audio, and making it a show,” Hazard continued. “And I love ‘Jeopardy!’ and their style of writing questions as well. They often give you a hint in the answer. There’s been clues where I don’t know the answer, but if you notice a little detail in there, you’re able to figure it out. Those details can make things fun, and I think are crucial elements to making a good trivia night.”


Here are five different trivia spots around town that contribute a little extra something to the local trivia night offerings.

730 Tavern

Most trivia nights hook players by awarding gift certificates to the bar or restaurant at which they’re hosted — but those certificates can’t be used on the same night as the respective trivia game. John Kinnally, the manager of 730 Tavern, prefers to award cash. “I know our food and drinks are good, so why make people wait?” Kinnally explained. The longtime radio host dishes out six cash payouts between $10-20 each during a 90-minute game, which lets players stay in the running for money even if they fall behind early. And unlike Stump or Geeks, there’s no limit to how many players are on each team. (Tuesdays at 7:30 to p.m.; 730 Massachusetts Ave., Cambridge)

Aeronaut Brewing Co.

Somerville’s Aeronaut Brewery has built a reputation for putting on unconventional events, including its trivia nights. Over time, the trivia night has built up a healthy community of regulars, and each week a different member (or members) of said community hosts the game. The end result is a trivia night that has garnered a regular rhythm over time, but still always offers a slightly different experience. (Tuesdays at 8 p.m.; 14 Tyler St., Somerville)

The Sinclair

The Sinclair is generally regarded as one of the best live music venues in the Boston area, so it makes sense that its trivia night is centered around rock ‘n roll. Hosted by Brett Milano (author of “Vinyl Junkies” and “The Sound of Our Town”) and Rockerzine.com editor in chief Erin Amar, the six-round, 60-question trivia night is a must for music fans, and is held on the first Tuesday of each month. (The first Tuesdays of each month at 8 p.m.; 52 Church St., Cambridge)

The Banshee


This Dorchester pub ups the stakes on the traditional weekly quiz offerings by rewarding repeat visitors. Along with a weekly gift card prize, the bar occasionally gives the top-scoring team over a monthlong period a much larger reward. The questions hit a variety of topic areas, but music aficionados will appreciate the difficult name-that-tune round, which is worth double the points of the other rounds. (Wednesdays at 8 p.m.; 934 Dorchester Ave., Boston)

The Druid

Wednesday nights at this Irish pub in Inman Square draw a packed house, which isn’t hard in such a snug venue. The questions here are a bit harder than the ones at your average trivia night, with questions sometimes skewing very local or vaguely niche, but the regulars are usually up to the task. Only the first place team wins a cash prize, but second and third win “something special from behind the bar,” and even the last place team doesn’t leave empty-handed. (Wednesdays at 8 p.m.; 1357 Cambridge St., Cambridge)