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Trivia Night in Portland, Maine: Where It Actually Happens Each Week (Verified Against the Venues' Own Pages)
The most useful thing to know about trivia in Portland is that it lives on brewery calendars, not in any directory. Wednesday has the most listings, Thursday is close behind, and the room that warns it fills up is the one with the pizza. Most of the lists you will find are a year or two old, written by someone summarizing a Facebook post. This one is built from the venues' own pages, read on October 30, 2026, and where a night could not be confirmed we say so instead of guessing.
Wednesday: the two big rooms
Foundation Brewing & Pizza. Foundation's events page lists trivia every Wednesday at 6 p.m., hosted by Mike from Hardly Trivial, and says a new season started Wednesday, September 2. The rules are the most specific of any venue we checked: old-school pen and paper, no phones during rounds, and a maximum of six players per team. The page also warns that the room usually fills up and suggests arriving early to get in the pizza queue. Wednesday is also their "2 Pints & a Pie" deal, two pints plus a Detroit-style pie for $25, which is the sort of arithmetic that explains the crowd. Our read: pick this one for a full, competitive night, and arrive early.
Bissell Brothers. Bissell's events page lists trivia every Wednesday in the taproom from 6 to 8 p.m., teams of 2 to 8, no registration required, with prizes for winners and the kitchen open. The bigger team cap makes this the easier landing spot for a group of seven friends who do not want to split up. It also has the lower barrier: nobody needs to book anything.
If you want a Wednesday decision rule: big group, show up and sit down, pick Bissell. Small serious team that wants the stricter format, pick Foundation.
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Thursday: a quieter, more varied night
Definitive Brewing. The Portland taproom's own site lists "Thursday Trivia 6-8pm," and a banner on the page says the first and second place teams win Definitive gift cards. We could not find a team cap or host named on the page, so ask when you arrive.
Bissell Brothers, again, with a twist. Bissell lists a JEOPARDY! Bar League every Thursday night, described as the official bar trivia experience from the quiz show. We read the listing but not a start time or any cost, so check the event page before you go. This is a different animal from a pub quiz, and it is the only licensed-format night we found.
Brickyard Hollow (Portland). The brewery's Portland page mentions "trivia on Thursdays" among the things going on in the space. It gives no time, and no host, so treat it as a signal to call or check their calendar.
Sunday: the one almost nobody lists
Bramhall (769 Congress Street). The host company Raise the Bar Trivia lists a Bramhall game on Sunday, November 1 at 7 p.m. on its own events feed. That matches the weekly Sunday 7 p.m. slot reported in earlier coverage, and it settles a point where one published list put Bramhall under Friday.
Allagash: confirmed, but not pinned down
Allagash's tasting room events page says "weekly trivia nights" are part of what happens at the Flagship tasting room. It does not give the weeknight on the page we could read, so we are not going to print one. A 2024 roundup put it on Fridays, but that is exactly the kind of claim that goes stale, so check the Allagash events calendar before you plan around it.
South Portland, as reported
The Portland Press Herald ran a May 2026 roundup of South Portland trivia that names Coppersmith Tavern and Table on Monday at 6:30, Evie's Ferry Village Watering Hole on Tuesday from 7 to 9, Rattle Shake Grill on Wednesday at 7, and Sea Dog Brewing on Wednesday with two rounds at 6 and 7. We could not load those venues' own pages, so treat these as reported, not confirmed, and verify before driving over. Of that list, the Tuesday Ferry Village game is the one worth the trip if you want a neighborhood-bar feel instead of a brewery crowd.
What we skipped
Several venues appear on older lists with a trivia night: Austin Street, Goodfire, Gritty McDuff's, Mast Landing, Smoked Portland and others. Their own sites either failed to load for us or did not mention trivia on the pages we could read, so they are not listed above. That is not a statement that the nights ended. It is a statement that we will not print a night we could not read. Trivia schedules change by season, and hosts move between bars with little notice.
How to pick, in practice
Go on a Wednesday if you want a crowd and you are happy to arrive early. Try a Thursday if you would rather avoid the Wednesday rush, though we have no attendance data to promise an empty room. Bring a team of four to six, since that fits every cap we found. Leave your phone in your pocket, because the stricter rooms ban it during rounds. And if you are new in town and playing alone, ask the host to place you with a team; most will. For other ways to meet people after you move, see our directory of clubs and groups that take newcomers and the Portland run club guide, since Bissell's own Run Club sends runners back to the brewery for discounted pours.
FAQ
What night is trivia in Portland, Maine?
Wednesday and Thursday are the two main nights. Foundation Brewing and Bissell Brothers both list trivia every Wednesday starting at 6 p.m., and Definitive Brewing lists trivia every Thursday from 6 to 8 p.m. Bramhall runs a Sunday game at 7 p.m. through Raise the Bar Trivia.
How many people can be on a trivia team in Portland?
It depends on the room. Foundation Brewing caps teams at six players, and Bissell Brothers allows teams of 2 to 8. Other venues did not publish a cap on the pages we read.
Do I need to register or book for trivia night?
Bissell Brothers says no registration is required. Foundation says the room usually fills up and recommends arriving early, but does not describe a booking system. Check each venue before a large group goes.
Is trivia free to play in Portland?
None of the venue pages we read listed an entry fee for their weekly trivia, and the prize structures mentioned are gift cards or prizes. We did not find a published cost for Bissell's Thursday JEOPARDY! Bar League, so confirm that one directly.
Are phones allowed during trivia?
Foundation Brewing bans phones during rounds and runs pen and paper only. Other venues did not state a rule on the pages we read.
Which Portland trivia night is best for a big group?
Bissell Brothers, because the published cap is eight players and no registration is required. Foundation caps teams at six.