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The Definitive Guide to Trivia and Game Nights in Portland

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The Definitive Guide to Trivia and Game Nights in Portland
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Art by Marc Patenaude

Hi ho! It’s cold and miserable out, and for the next few months anyway, there’s no urgent electoral politics to bang your head against. That means it’s a perfect time to do things like nurture friendships. That timeless task is essentially the backbone behind trivia night (don’t let the know-it-all pals tell you otherwise).

Along with bingo and board games, these public gatherings are Maine winter staples where you can make questionable food choices, not watch Netflix, and flex your esoteric interests in front of friends and loved ones (and let them forgive you when you get something wrong).

From trivia nights, bingo, karaoke, open board game sessions and more, here’s a (near-)comprehensive list of your options in Greater Portland. 

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James Curwood runs a Geeks Who Drink-style trivia at Bull Feeney's every Monday night

MONDAY 

Old Port 

Hosted by the local chapter of Geeks Who Drink, a nationwide effort to promote competitive nerdiness, Bull Feeney’s trivia night at 7 pm is known for its hyperspecific themes. Past quizzes have been dedicated to some of our favorite fictional universes including Star Wars, Harry Potter, The Office, and Seinfeld. Bull Feeney’s proves to be a great place for this sort of thing, with plenty of seating and a menu of Irish pub fare like lamb stew and whiskey-steamed mussels to keep you busy between rounds.

It’s a cavernous den over at Sebago Brewing Company in the Old Port, where a guy named Rick founded one of the city’s most time-honored and institutional trivia nights (and has since deployed his charge to numerous fact-bearing acolytes both here and at the Sebago in Kennebunk).

Sure, Arcadia National Bar has tons of cool video games and pinball machines to sink an hour or two into, but it’s also fantastic place to nerd out over some classic tabletop strategy games. It remains the only place in town to crack open some Magic the Gathering booster packs and draft the latest Guild of Ravnica set with 6-8 others for $10 every other Sunday. Booster drafting is great for casual or beginner players — as you don’t need to bring any cards and everybody drafts from the same card pool — but if you’re a more competitive spellslinger, bring your 100-card deck to Commander Night every Monday starting at 7 pm. 

Bayside 

Monday nights aren’t boring at Bayside Bowl. Trivia starts at 7pm up on the mezzanine (with over $70 in prizes on the line) and after 8 pm the bowling lanes are open for just $10 an hour. Of course, these activities require actual human friends, and if you’re in need of some check out the “Lonesome No More Club,” a Reddit community of disaffected young adults who are looking to reboot their social life by bowling and playing trivia with other random strangers they just met online. This group is considering Bayside for their future meet-ups because it offers cheap thrills and generous piles of tater tots.

West End

Funnyman Krister Rollins hosts a trivia night at tapas restaurant Local 188 called "The Spanish Inquisition," where they offer half-priced bottles of wine every Monday at 9:30 pm.  

Off-Peninsula 

It fits our definition of a dive, and we love the atmosphere at the Spring Point Tavern. Frequented by college kids and middle-aged folks alike — there’s an auto shop and a college campus right across the street — this spacious pub hosts a trivia night every first and third Monday of the month. And the dude who runs it loves to include some tidbits of local lore in his questions, so you best know Portland! What’s at stake? Hoodies, hats, neon signs, posters, glassware — really whatever the owner is feeling like that particular week. Elsewhere in the area, a dude named Don Corman hosts a trivia night at Moe’s Original BBQ at 7, where prizes range from gift cards to the restaurant and occasionally sponsoring breweries. We’re also obliged to tell you that the Tilted Kilt runs a trivia night at 7, and Pizzeria Uno does up a “speed quiz” at 9. You do you!

In Old Orchard, Caleb Biggers runs “brain busting trivia” at Jimmy the Greek’s in the center of town. One of the more compelling setups we found is at Run of the Mill in Saco. Owner Geoff Houghton hosts, and participating teams pay $10 to play ($15 for teams of more than 5 people). That money gets split two equally at the end of the night — between the winning team and the team that finishes squarely in the middle. That’s right, mediocrity will get you that bread.

TUESDAY 

Old Port 

Winter demands that you crawl in tight and cozy spaces, and Dogfish Bar and Grille offers just that — plus twinkle lighting! Apart from weekly live music showcases, Dogfish hosts a trivia night every Tuesday at 8 pm captained by Mat Yerkes, where young and old test whose better versed in music, T.V., and movie obscura for a chance to win “bar swag” and occasionally bigger prizes on multi-week competitions, all while you munch on nachos in a welcoming basement-y interior. A coupla guys named Ben and Nate mounted a trivia night at hotspot burger joint Black Cow Burgers and Fries on Exchange Street last month, generating questions for a two-team winners’ payout of Black Cow gift cards. Trivia night at Ri Ra can get kinda serious. Questions lean heavy into music and pop culture with several of them involving identifying the songs playing over the loudspeaker. Prizes include a $35 gift card to Ri Ra and some swag in the form of t-shirts and hats from Downeast Brewing, who is sponsoring the event for December. We recommend you munch on their chicken bites while you play because they’re not previously frozen and that makes a difference.

East End 

Halfway up Congress Street, Munjoy Hill Tavern also hosts a trivia night every Tuesday, keeping up the community flourish as the grittiest spot on the hill. And Howie’s Pub, overlooking Washington Ave, hosts a really solid one at 6:30 pm with way-cheap pizza specials, run by the dude himself (Howie, we mean).

West End 

Margaritas may be a corporate chain in a city whose residents love small local businesses, but trivia night gets pretty packed. Keep those $3 margaritas coming while you act smart every Tuesday night from 7 to 9. The host is known to be a funny dude.

Off-Peninsula 

There’s a Geeks Who Drink-style trivia at Foulmouthed Brewing across the bridge. The popular Geeks Who Drink staff host their spin out questions every Tuesday at 7 pm at this cozy little brewery in South Portland’s Knightville neighborhood. Come for the prospect of winning bar cash, stay for the decadent poutine. Another Geeks Who Drink-hosted affair is in the little college hamlet of Gorham, where School Street Pub across from USM presents a trivia night at 8, winners getting meals and drinks comped. There’s also a pub quiz at O’Reilly’s Cure, an Irishish bar on Route 1 in Scarborough (giving away rink-side Bruins tickets this December), while in South Portland, Willow’s Pizza hosts a game of “musingo,” a game where players dot bingo boards after hearing song snippets.

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The trivia scene at Bayside Bowl Monday nights

WEDNESDAY 

Old Port — While dance nights and light shows dominate Brian Boru on the weekend, the mid-week hump is for answering questions. At 7 pm, they host one of the rare trivia nights in town offering cash prizes (or more beer money, depending on your perspective). Winning teams get $50 for 1st place, $25 for 2nd, and $15 for 3rd, covering 40 questions that range from history and geography, to music and sports. The owner at Boru says he’s about to start offering a killer nacho deal for trivia teams, on top of their 50 cent wing specials and tap of 18 local beers. Over at Gritty’s Brewpub in Portland, WCYY radio personalities Rob and Joey sling a popular trivia night at 7 pm, with prizes of the short-term (gift cards of varying dollarge) and long-term (skydiving passes, ski rentals, other seasonal outdoor adventure stuff) variety.

West End — Another Geeks Who Drink jawn, Salvage BBQ and their rows and rows of picnic-style tabling is a picture-perfect set-up for trivia. Winners here receive gift cards, beer sponsor swag, and sip on random beer specials over the night.

Off-Peninsula — A separate trivia company, Stump Trivia, produces all material for Sea Dog Brewing Company’s trivia night, so maybe expect a lot of sports and pop culture questions? A 10-minute drive away in South Portland, this option’s perfect for the person that doesn’t want to deal with Old Port parking, yet wants to eat well while playing. And while we’re at it, we’ll totally plug Foulmouthed Brewing’s “Pints and Purls” crafting night, because drinking beer and knitting in public is pretty much the coziest idea in the frigging world.

Elsewhere Wednesdays, if you want community gaming (in the vein of Settlers of Catan, Scrabble, Exploding Kittens, that sort of thing), head to Westbrook at Quill Books and Beverage, which hosts their own board game night roughly every Wednesday. Down in Biddo (where the locals totally call it that), the still-sorta new Cowbell Burger Bar hosts a Family Feud-style trivia night at 7 pm, with prizes ranging from gift certificates to the occasional bowling pass or major market sports ticket (though do you really wanna see these Celtics?)

THURSDAY 

Old Port

Trivia at Binga’s Stadium is particularly fun because they do it Family Feud-style, where you might be asked to, say, rank the top five Spanish speaking countries, or, like, the top five most famous wizards. Point is, prompts are all over the place. Speaking of families, you could your bring your kids to this one — there are no raunchy questions and the spacious interior, dizzying amount of televisions, and cheap finger food makes Binga’s quite kid-friendly. Prizes vary from mugs, steins, gift cards, t-shirts and tickets to the next Mariners game.

West End

Thursday is, as your ride-or-dies know, where Hall of Fame karaoke maestro DJ Cougar has posted up every week at Flask Lounge for the last 10+ years (though he’s been working the circuit for much longer — anyone remember Bottomz Up?). Flask gets high marks as a karaoke room (and yes, karaoke is a game) because of its odd, antechamberish dimensions and soft dungeony vibes. You can be someone else here, whether that’s David Lee Roth, Rihanna, or Lisa Loeb. It’s at 9.

Off-peninsula

The sports bar/pizza hub Profenno’s in Westbrook holds a trivia night hosted by a guy named John Hilton every Thursday at 9 pm, where you can carb-load on solid pizza and pub fare and try your hand against local stalwarts. And up in Brunswick, Flight Deck Brewing runs a doozy from 6-8 pm.

FRIDAY 

Old Port

The nights of soft contemplation behind you, Friday nights usually sort themselves out with brighter-lit entertainment, but there’s always a nuclear option at the Silver House Tavern, an ageless Commercial Street haunt that hosts karaoke Friday and Saturday nights. The writer of these words thought it was a good idea to sing “Rocket Man” there in like, 2009, and while the sound system made his voice sound a little more like Bernie Taupin’s than Sir Elton, it’s nonetheless a memory that survives today.

Off-Peninsula

It’s not every week, but Quill Books and Beverage in Westbrook tells us they host a “queer trivia” once a month or so, typically falling on Fridays. Winners get gift cards to this lovely book and bistro.

SATURDAY 

West End

Although there are no scheduled events, Union Station Billiards provides plenty of outlets for the competitive spirit and enough cheap beer specials to fuel them. It’s got a bit of a dive bar meets man-cave vibe, complete with neon Budweiser signs, but it benefits from a cavernous interior that’s typically very clean, well-lit and packed with things to do from billiards, foosball, ping pong, air hockey, arcade games, darts, and a jukebox. Solid french fries too.

Off-Peninsula

While they axed their trivia night, there’s a decent karaoke spot at Seasons Grille, which is indeed the restaurant adjoining the Ramada Hotel. Do you dare drop your best “Summer of ‘69” here?

SUNDAY 

Old Port

It’s a bit of an older crowd at the Old Port Tavern, but they might be the best folks to hear your drunk and sloppy rendition of R.E.M.’s “Losing My Religion”. Karaoke starts at 10 pm here and goes Sunday through Thursday (so you can apply it all week if you like), so you’ve got plenty of chances to make a fool of yourself. If things get too weird know that you can always escape upstairs and shoot pool on one of their six tables.

West End 

Bingo night at Salvage BBQ is easily the best way to wet your daubers without having to go out to the mall (which is also a hoot). Lovingly and animatedly hosted by Lex (of bluesplaying fame) and Amber, they routinely give out $20 gift cards to Salvage (or sister ‘straunts Local 188 and Black Cow) as well as seasonally curated gift packages, like “sun-screen and bug spray int the summer, buckets of Halloween candy in the fall, and practical stuff like snow shovels and and electric tea-kettles and whimsical stuff like disco ball bluetooth speakers.” If you’d rather a more active approach to the table, it’s a busy night at Blackstones, where Jerry runs karaoke from 6-9 and the best pool table in the West End is the site of an 8-ball tournament at 6 pm. 

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