Chicago Puzzling • August 2025
Crossword Fest, Blood on the Clocktower, Puzzled Pint
Midwest Crossword Tournament returns [Oct 4]

The second Midwest Crossword Tournament will be held October 4 at University of Illinois Chicago, 750 S. Halsted St. An all-Midwest team of editors, organizers, and constructors (previously published in The New York Times and other outlets) will present six crosswords. Plus: a mid-tourney game by yours truly! Last year was my first time at a crossword tourney and it was hella fun. Just lots of lovely word nerds to hang out with.
If you're wondering if this is an event just for speed solvers, I'll repeat what I pasted last year, from my friend Ben:
Much like a marathon, a crossword tournament is not so much about 'winning' as it is the unique experience and camaraderie. It’s a celebratory gathering of like-minded people. All types of solver are in the room, beginners are welcome and people enjoy it regardless of skill level.
Details and registration are here:
P.S. Here's a brand-new free preview crossword.
Blood on the Clocktower @ Demo Brewing [Aug 13]
I'm storytelling a night of Blood on the Clocktower, the social deduction game, at Demo Brewing in Ravenswood. There are only 16 spots available. It's open to veterans and beginners alike. As long as you're willing to lie, and be lied to (as you play the game), you'll have a blast. It's free to come, just plan to buy some drinks while you're there.
Blood on the Clocktower is (imho) the best social deduction game out there. If you know Werewolf or Mafia, it’s similar in structure, but it fixes for all the bad parts, and adds improvements that make it a really twisted, almost solveable logic puzzle.
Here's an official video from the creators about how to play.
Puzzled Pint: Orville Peck [Aug 12]

Puzzled Pint is tomorrow! The theme is, incredibly, the young alt-country music sensation Orville Peck. Never have I been more excited about a set this niche.
Chicago has two locations for Puzzled Pint!
- At Marz Community Brewing Company in Bridgeport (map) at 6:30 PM. RSVP here.
- At The Reveler in Roscoe Village (map) at 6:30 PM. RSVP here.
Also…
Don't forget to play my daily word game Raddle! Currently we're celebrating dogs.

Til next time,
-Sandy