The Crossword Show with Zach Sherwin

When:
Saturday, Dec 06, 2025 7:00p -
8:00p

Where:
WBUR CitySpace
890 Commonwealth Ave
Boston, MA 02215

EventScheduled OfflineEventAttendanceMode

Admission:
$10-35

Hosted by:
...
wburcityspace WBUR CitySpace

Categories:
Date Idea, Drinks, Games, Good for Groups

Event website:
https://www.wbur.org/events/1031581/the-crossword-show-with-zach-sherwin-2

The Crossword Show returns to CitySpace for a performance of "Puzzle #3: Cross Country," revamped and turbocharged for 2025. Heads up, regulars: this will be the Boston debut of this particular puzzle and show. Host Zach Sherwin (“Crazy Ex-Girlfriend,” “Epic Rap Battles of History,” MAD Magazine) presides as two guest comedians solve an actual crossword puzzle live onstage, with everything displayed on our screen so you can follow along. It’s like the New York Times crossword meets NPR’s “Wait Wait Don’t Tell Me,” with more rap than you’d expect.


As the solvers decipher the clues, Sherwin takes the show down rabbit holes of comedy, music, wordplay and trivia, all inspired by the answer words. Everything ties together at the end for a grand finale that’s as satisfying as it is mind-blowing. You don’t need any crossword expertise to be dazzled by this delightful, brainy, one-of-a-kind experience!

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12/06/2025 19:00:00 12/06/2025 20:00:00 America/New_York The Crossword Show with Zach Sherwin <p>The Crossword Show returns to CitySpace for a performance of "Puzzle #3: Cross Country," revamped and turbocharged for 2025. Heads up, regulars: this will be the Boston debut of this particular ...

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