PRIVATE EVENT | WS DEVELOPMENT TRIVIA NIGHT
2026-06-11 16:00 - 17:00 (America/New_York) | WS Development, 33 Boylston St, Ste 3000, Chestnut Hill, Massachusetts, 02467
A little friendly competition and team-building fun!

OH, JACKIE O! Famous Jackies Trivia & B-day Celebration
2026-06-15 19:00 - 21:00 | The Hollows, 248 Holland St, Somerville, MA, 02114
Join us every Monday night at The Hollows for Trivia Night!

Some Jackies are legendary. One of them works at The Hollows! 🥂

Oh, Jackie O! is a trivia night devoted to the most iconic Jackies across arts, pop culture, film, music, TV, and sports — and we’re doubling the fun with a birthday party for The Hollows’ own Jackie Olivia. 🎂

Think you know your Jackies? Come prove it.

🗓️Monday, June 15th

⏰Doors open at 5pm · Trivia kicks off at 7pm

📍 The Hollows — 248 Holland St, Somerville, MA (Teele Square)

🎉 Free to play | Teams welcome | Birthday energy required

🍹Specialty Drinks 🧑‍🍳Delicious Food 🏆Prizes 🥇Bragging Rights

THURSDAY NIGHT TRIVIA
2026-06-18 18:00 - 20:00 | Citizens House of Blues Restaurant & Bar, 15 Lansdowne St, Boston, MA, 02215
Grab your smartest friends (and maybe even your frenemies) to battle it out for bragging rights and an amazing prize — FREE tickets to a House of Blues show of your choice!

Yes, the winning team takes home free tickets to an upcoming HoB show. You’ll test your knowledge on everything from pop culture to (somewhat) obscure history, music to movies, not to mention some wild categories we’ll throw at you. And don’t worry, our trivia is Goldilocks approved — it’s not too hard or too easy, it’s just right!

Cold drinks, hot competition, and an outstanding music playlist awaits. No cover, just bring your A-game.

STATIC & NEON: 80s Trivia Night
2026-06-22 19:00 - 21:00 | The Hollows, 248 Holland St, Somerville, MA, 02114
Join us every Monday night at The Hollows for Trivia Night!

🌈📼 STATIC & NEON: 80s TRIVIA NIGHT 📼🌈

Dust off your acid-washed denim, tease up your hair, and get ready to time travel — Titletown Trivia is bringing the most rad(ical) decade back to The Hollows for one night only! 🕹️✨

🎬 Movies, 📺 TV, 🎵 music, 👾 video games, and all the pop culture you grew up on (or wish you did)… we have, like, got it all.

Think you know your Goonies from your Gremlins? Your synth-pop from your hair metal? Prove it. 💪

📅 MONDAY, JUNE 22🚪 Doors at 5PM🧠 Trivia from 7–9PM📍 The Hollows | 248 Holland St, Somerville

🆓 FREE TO PLAY🏆 PRIZES🍹 DRINK SPECIALS🍺 INDUSTRY NIGHT SPECIALS

PRIVATE EVENT | BRISTOL MYERS SQUIBB SUMMER PARTY
2026-06-24 15:00 - 17:00 | Tavern in the Square, 810 Constitution Ave, Littleton, Massachusetts, 01460

PRIVATE EVENT | BRISTOL MYERS SQUIBB SUMMER PARTY, Part 2
2026-06-25 15:00 - 18:00 | Tavern in the Square, 810 Constitution Ave, Littleton, Massachusetts, 01460

POP MAJESTIES TRIVIA NIGHT
2026-06-29 19:00 - 21:00 | The Hollows, 248 Holland St, Somerville, MA, 02114
Join us every Monday night at The Hollows for Trivia Night! This week’s show:

👑 POP MAJESTIES TRIVIA NIGHT 👑

The crowns are coming out. 👑✨

Get ready to test your knowledge of pop culture’s true royalty 🎬🎤📺🎭 — the Kings & Queens of movies, music, TV, and stage who’ve defined entire eras. Legends only. 🌟

So grab your squad, bring your best trivia game and find out if you really know your icons from your imposters. 🧠🔥,

📅 MONDAY, JUNE 29🚪 Doors at 5PM🧠 Trivia from 7–9PM📍 The Hollows | 248 Holland St, Somerville

🆓 FREE TO PLAY🏆 PRIZES🍹 DRINK SPECIALS🍺 INDUSTRY NIGHT SPECIALS

📲 Reserve your spot today!

PRIVATE EVENT | SIDLEY AUSTIN LLP
2026-06-30 16:00 - 18:00 | Sidley Austin LLP, 60 State St, 36th Floor, Boston, Massachusetts, 02109

THURSDAY NIGHT TRIVIA
2026-07-09 18:00 - 20:00 | Citizens House of Blues Restaurant & Bar, 15 Lansdowne St, Boston, MA, 02215
Get ready to put your not-so-useless knowledge to the test and enjoy a lively night of trivia at House of Blues Restaurant & Bar!

Grab your smartest friends (and maybe even your frenemies) to battle it out for bragging rights and an amazing prize — FREE tickets to a House of Blues show of your choice!

Yes, the winning team takes home free tickets to an upcoming HoB show. You’ll test your knowledge on everything from pop culture to (somewhat) obscure history, music to movies, not to mention some wild categories we’ll throw at you. And don’t worry, our trivia is Goldilocks approved — it’s not too hard or too easy… it’s just right!

Cold drinks, hot competition, and an outstanding music playlist awaits. No cover, just bring your A-game.

MONDAY THE 13TH: A NIGHTMARE ON HOLLAND STREET TRIVIA NIGHT
2026-07-13 19:00 - 21:00 | The Hollows, 248 Holland St, Somerville, MA, 02114
Join us every Monday night at The Hollows for Trivia Night! This week’s show:

🔪 MONDAY THE 13TH: NIGHTMARE ON HOLLAND STREET 🔪A Horror-Themed Trivia Night

Friday the 13th is busy, so it’s sending Monday instead. Equally cursed, just slightly more inconvenient.

Round up your final girls, your himbo-who-dies-first, and the friend who insists on splitting up to cover more ground (don’t). It’s a night of slashers, scream queens, questionable cabin choices, and the movies that taught us never to say “I’ll be right back.” Think your trivia knowledge can survive the night? Statistically… it probably won’t.

📅 Monday, July 13📍 The Hollows — 248 Holland St, Teele Square, Somerville⏰ 7:00pm – 9:00pm (doors at 5pm)🎟️ Free to play🏆 Prizes for whoever makes it to the credits

🍹 Drink specials🍺 Industry night specials

📲 Reserve your spot today!

PRIVATE EVENT | AVALONBAY SUMMER PARTY
2026-07-20 12:00 - 13:00 | AvalonBay, 600 Atlantic Ave, 35th Floor, Boston, Massachusetts, 02210

SKETCHY BEHAVIOR: AN ANIMATED TRIVIA NIGHT
2026-07-20 19:00 - 21:00 | The Hollows, 248 Holland St, Somerville, MA, 02114
🖍️ SKETCHY BEHAVIOR: AN ANIMATED TRIVIA NIGHT 🖍️

Titletown Trivia is taking over The Hollows for a night dedicated to everything animated: the shows that raised us, the ones we probably weren’t supposed to watch, and the ones we still rewatch as “adults.” Get ready for full toon immersion.

WHAT TO EXPECT:🎨 2 games covering Saturday morning classics, Disney/Pixar, adult animation, anime crossovers, cartoon villains, iconic theme songs, and more🧠 Trivia for casual fans AND the person on your team who still argues about Kim Possible lore🏆 Prizes for the top toon-brained teams

🍸 Drink specials🍻 Full food menu at The Hollows all night

THE DETAILS:📅 Monday, July 20⏰ Trivia from 7-9 PM — doors at 5pm📍 The Hollows, 248 Holland St, Teele Square, Somerville🆓 FREE to play👥 Teams & solo players welcome

👉 Reserve your spot — this one’s gonna draw (get it?) a crowd.

MUSIC & POP CULTURE TRIVIA NIGHT
2026-07-23 18:00 - 20:00, 2026-07-30 18:00 - 20:00, 2026-08-06 18:00 - 20:00 | Citizens House of Blues Restaurant & Bar, 15 Lansdowne St, Boston, MA, 02215
Play for a chance to WIN CONCERT TICKETS to a House of Blues show of your choice!

This is NOT your run-of-the-mill trivia night with lame questions and even lamer prizes! We’ve got TWO games with music & pop culture questions that are not too easy, not too hard, but rather, JUST RIGHT!

We also have FREE House of Blues tickets on the line for the winning team in EACH game — YOUR choice of show!

So round up your smartest friends (or fly solo) and battle it out and answer questions across all kinds of pop culture categories, from music & movies to social media & current events.

Come hungry, come thirsty, and come ready to compete. Doors open early… arrive before 6PM to grab your table!

The Rundown:

🎵 Music & pop culture trivia

🏆 Win concert tickets to a House of Blues show of your choice

🍹 Full bar + restaurant menu available

🔞 Ages 18+

🎉 Solo players & teams welcome

📍 House of Blues Restaurant & Bar | 15 Lansdowne St, Boston

🗓️ Every Thursday

⏰ TWO games: 6PM & 7PM

THAT'S WHAT SHE SAID: THE OFFICE TRIVIA NIGHT
2026-07-27 19:00 - 21:00 | The Hollows, 248 Holland St, Somerville, MA, 02114
Join us every Monday night at The Hollows for Trivia Night!

Bears. Beets. Battlestar Galactica. If you can recite Michael Scott’s worst puns from memory, know exactly why Dwight keeps a Bobblehead Award on his desk, and have strong opinions about the Cornell vs. Scranton branch rivalry, this one’s for you!

Titletown Trivia is bringing a full night of The Office trivia to The Hollows, testing your knowledge across all nine seasons of Dunder Mifflin’s finest (and most chaotic) employees. Expect questions on iconic cold opens, Schrute Farms lore, Jim and Pam’s world-class pranks, Creed’s unexplainable everything, and plenty of “that’s what she said”-caliber categories.

📅 Monday, July 27🕖 7:00 PM – 9:00 PM📍 The Hollows | 248 Holland St, Somerville, MA

✅ Free to play🍹 Drink specials all night💼 Industry night specials for service industry folks🏆 Prizes for the winning team

Grab your work wife, your work husband, and anyone else who’s ever quoted the show unprompted… teams of any size welcome. Space fills up fast, so reserve your spot today!

PRIVATE EVENT | COOLEY LLP SUMMER PARTY
2026-07-29 18:00 - 19:00 | STK Steakhouse, 222 Berkeley St, Boston, Massachusetts, 02116

TRIVIA MISÉRABLES: A NIGHT OF BROADWAY BELTERS
2026-08-03 19:00 - 21:00 | The Hollows, 248 Holland St, Somerville, MA, 02114
Join us every Monday night at The Hollows for Trivia Night!

Do you hear the people thinking? 🎭

Assemble your team and storm the barricades of trivia! Two games covering Broadway’s biggest hits, from Hairspray to Hamilton, West Side Story to Wicked. Showstoppers, one-hit wonders, and deep-cut deep cuts. Musicals, melodramas, movie adaptations. We’ve got it all.

One night only. No singing required (but we won’t stop you).

📅 Monday, August 3rd🕖 7:00 PM – 9:00 PM (doors at 5 PM)📍 The Hollows | 248 Holland St, Somerville, MA

✅ Free to play🍹 Drink specials all night💼 Industry night specials for service industry folks🏆 Prizes for the winning teams

Les Quizérables await. Will you answer the call?
