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The Ultimate Guide to Trivia Nights in Annapolis

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Do you have a ton of random knowledge and a desire to test it? Or maybe you’re an expert in a couple of areas—an O’s stats nerd, a diehard Swiftie, or a world-renowned authority on mollusks. Whether you’ve got a hodgepodge of info about movies, history, or heavy machinery (thanks to my toddler, I feel pretty confident about my ability to name construction vehicles), one of our local trivia nights is the way to share it. 

These competitions are a fun reason to get out of the house and have some bonding time with friends, family, and coworkers. So this intrepid reporter ventured out to a few locations to give you the lowdown on how to make trivia night your weekly routine.

Trivia Night Part 1: Crooked Crab Brewing Company

Address: 8251 Telegraph Road, Suite D, Odenton, MD 21113
Day/Time: Wednesdays, 7 PM
Trivia Host: Geeks Who Drink

Crooked Crab Brewery in Odenton has a very popular trivia night on Wednesdays, so you should try to get there early. I did not. I ended up parking in the back in a spot that was maybe not an actual spot. Who’s to say?

As for trivia, I had some bad luck. The company that puts on the event canceled after being unable to find a last-minute replacement for its usual host. Instead of a traditional trivia night, they handed out the questions to each group so you could do it yourself. I’ve been assured it’s a fun time, the company is normally very reliable, and this was a one-time thing. 

If you decide to try it, keep in mind that they allow up to eight people per team. They have pizza made in-house and plenty of drinks on tap. Winners will receive a $25 gift card and second place gets a $15 gift card. They also have seasonal tournaments where the winning team earns 20 oz. “trivia champion” mugs, which they can use the following season for full pours at regular pint prices. And while I didn’t get to do trivia, I didn’t leave empty-handed. I made sure to grab a six-pack of Haze for Days.

Trivia Night Part 2: Pherm Brewing Company

Address: 1041 MD-3, Gambrills, MD 21054
Day/Time: Thursdays, 7 PM
Trivia Host: Trivia Maryland

On Thursday nights, this brewery in Gambrills packs the house with trivia contestants…and a few dogs, too. You won’t have much trouble parking, but you should get there early to snag a good table. The room is long, with the screen and trivia host at one end. If you hit traffic, you may end up in the nosebleeds. 

I joined my friend and their team of high school teachers. This worked out well for me. Not only was I on a team that was really good, but they could help me understand the point system. The score sheet lays out the rules pretty well, but it’s useful to have someone explain it. For half of the questions, you pick a number that represents the confidence of your answer, and that’s how many points you’ll get if you’re right. The other half are multi-part questions and the points vary based on how many you get right. Plus there’s bonus point questions. I let my teammates handle the math. (They’re math teachers, so it’s only fair.)

Pherm doesn’t serve food, but a different food truck parks outside each night. The atmosphere is fun and a little wild. Expect some friendly heckling from both the crowd and the host. The energy kicks up more as the night goes on, and by the final question it feels like the stakes are high. And for dedicated trivia teams who are part of the ongoing tournament, those stakes are real. There’s $1,000 up for grabs at the World Series events. Start studying!

Trivia Night Part 3: Neo’s Pizza Annapolis

Address: 220 Harker Pl Suite 145 , Annapolis, MD 21401
Day/Time: Mondays, 7:30 PM
Trivia Host: Charm City Trivia

At Neo’s Pizza in Annapolis Town Center, Charm City Trivia hosts the trivia night. They’re part of Charm City Entertainment, and they hold dozens of games across Maryland. There’s a good chance that a trivia night you attend may have them involved. 


Parking is easy for Annapolis Town Center, since the Target garage is right next to Neo’s. This is another dog-friendly venue, which comes highly recommended by Kramer, the goldendoodle who welcomed me. 

I tried my hand at being a solo player. But I needed the host, Sarah, to help with the rules and points system. Like at Pherm, the wagers took me a minute to get the hang of, but I got comfortable quickly. And being a team of one had its benefits: I turned in my (mostly wrong) answers quickly, and I didn’t have to share food! I ended the night in third…from last. The usual prizes are gift cards to Neo’s: $15 for first place, $10 for second place, and $5 for third place. Extra prizes are offered on “tap takeover” days, where a brewery comes in with their products. This occurs about once a month.

Neo’s has table service, so you don’t need to leave your seat to get pizza. You don’t have to get there super early for a decent table, either. This is an audio-only game, with Sarah reading off the questions without the aid of a screen or other visual clues. It was a very relaxed and chill vibe for the entire game, which Sarah told me is how it usually feels. And the game came in under two hours! I like that kind of efficiency.

Trivia Night Part 4: O’Loughlin’s

Address: 1258 Bay Dale Drive, Arnold, MD 21012
Day/Time: Tuesdays, 7:30 PM
Trivia Host: Amanda’s Trivia

O’Loughlin’s in Arnold is another popular trivia night where you should get there early. (Don’t worry, I did this time.) Tables are not promised, so everyone is added to a waitlist. The event takes place in two areas separated by a wall, but the strategically placed speakers make it easy to hear the questions. If you’re lucky, you’ll get a cozy spot by the fireplace. If you’re luckier, you’ll get to sit near Amanda, who runs the trivia game. She’s not part of a larger company, so she comes up with the questions herself. There’s a good mix of challenging and knowable questions for those who pay attention to the world. And she drops Easter eggs and hints throughout. She’s both close with regulars and instantly welcoming to new players. 

I ate my shrimp tacos (it was Taco & Trivia Tuesday, after all) while the game got started. Another team noticed that I was alone and asked me to join them. This gets at something I’ve learned: the trivia crowd is friendly, so this is a great activity for anyone who might be a bit shy. And the competition is less intense here than at places that hold big, ongoing tournaments.

The scoring system is not complicated. You write all your answers for a single round on one paper, which you turn in at the end of the round. Correct answers equal points. There’s the potential for a tiebreaker at the end to see who gets first place (a $30 gift card to O’Loughlin’s) or second place (a bottle of wine, with your choice of the color). My team came in fifth or sixth place, which is pretty good given how many teams there were. 

You can find Amanda at O’Loughlin’s on Tuesdays, Molloy’s in Gambrills on Wednesdays, and Anthony’s in Bowie on Mondays. You’re bound to have fun if she’s there.

Tips for a Good Time

  • You don’t have to participate the first time. Feel free to visit and observe. Enjoy the food, drinks, and atmosphere to see if it’s a good fit. And you’ll see the kinds of questions they ask so you can join next time.
  • Plan to be out for a while. These events typically run about two hours, but may go on later than that. It’s a night out, so maybe don’t skip the afternoon caffeine.
  • No one to go with? No problem! When you get there, start with the host. They’re used to seeing regulars and new people, so they can offer suggestions and give you the lay of the land. Then see if there are smaller teams of about two or three people. Ask them if you can join their group! 
  • Bring some supplies. Some trivia hosts, such as Charm City Trivia, have pens you can use. But bringing your own pens and paper come in handy. And if you’re near-sighted (like me), don’t forget your glasses! Some games are audio-only, but others use a screen. 
  • Look for clues on social media. Trivia hosts may put a clue for that evening’s game on their Facebook or Instagram pages. If you don’t use social media, check with your teammates or the host to see if they’re willing to show you.
  • Get creative with your team name. There are team names of all stripes. You can go with rhyming, puns, inside jokes, or just something deeply silly. I have to give a shout-out to team Bed, Bath, and Your Mom at O’Loughlin’s as my favorite. But if you need a jumping-off point, here are some other ideas:
    • For Moms:
      • Bad Mama Jamas
      • Mothers Know Best
      • MamaMommyMomBruh
      • Mother Shuckers
      • I’m Literally Just a Mom
    • For Parents:
      • Dino Nugget Dieters
      • The Minivan Caravan
      • Diaper Bag Demons
    • For Marylanders:
      • Let Them Eat Crab Cake
      • Pink Flamin-Goes to Washington
      • Poto-Mac ‘n’ Cheese
      • Old Bay Reasoning
    • Or let your kids name your team! Yes, that is a recipe for disaster, since you may get anything from potty jokes to 6-7 references. Don’t say I didn’t warn you.

More Trivia Night Locations

And there are three locations that used to have trivia nights, but don’t anymore: 1747 Reynolds Tavern, RegionAle (their Annapolis location closed recently), and The Trophy Room at Graduate by Hilton, Annapolis.

Mom-brain? Never heard of her. You’ve got knowledge to show off, whether you are a master at math, a whiz with world history, or just a really good guesser. Use those mental muscles and make some new friends while you’re at it. So get out there and get your trivia on!

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About Elizabeth Krischer