WESTPORT, CT — On his way to winning his fourth consecutive Annual Crossword Puzzle Contest in Westport on Saturday, Norwich resident Glen Ryan nearly got tripped up by this clue, “Philippine Island that’s home to Iloilo.”

The answer is Panay, and Ryan didn’t know it. But one of the beautiful things about crossword puzzles is that you don’t always have to know the answer right away.

“The puzzle wasn’t particularly hard, but I didn’t know the Philippine Island,” Ryan told Patch after his victory. “Fortunately, I was able to get enough clues around it to get enough letters to figure it out.”

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The other clue that nearly tripped him up? “Trend for unengaged employees.” The answer was “quietquitting.”

“I had a little trouble with that one, too,” Ryan said.

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Considering he won on Saturday with a time of 6 minutes, 7 seconds, he clearly didn’t struggle too hard.

Saturday marked the 25th year that the Westport Library has held the crossword puzzle contest, which is hosted by New York Times Crossword Editor Will Shortz.

To the crossword set, Shortz is probably the equivalent of Michael Jordan, but he comes to Westport to host the event each year, one of only two crossword events he hosts annually. The other being the American Crossword Puzzle Tournament, which was featured in the documentary “Wordplay,” and is held at the Stamford Marriott in April.

Ryan has won the Westport contest a total of six times, but he says he’s only been able to crack the top ten in the American Crossword Puzzle Tournament.

“I’m not in their league,” he said.

On Saturday, Ryan beat runner-up Ken Stern, who finished the championship puzzle in 6 minutes, 58 seconds, and third-place finisher Peter Rimkus, who had a time of 10 minutes, 12 seconds.

The three were the same three finalists in the 2023 Westport contest.

According to organizers, 150 people participated in Saturday’s event, filling the library’s Trefz Forum.

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The contest consists of three, as-yet-to-be-published New York Times crossword puzzles. Participants are given 20 minutes to complete each one, and the puzzles become more challenging after each round. The three finalists are chosen based on how fast they completed those puzzles without errors.

Participants who complete a puzzle with no errors receive a certificate. Additionally, the contest also recognizes the players with the best penmanship in filling out their puzzles: Brian MacDonald who used ink, and Brittany Wayne who used pencil.

Bill Harmer, the library’s executive director, was the emcee for Saturday’s event, a role he cherishes, in part because the event is a showcase of the library’s diversity of offerings.

“We’re very fortunate that Will comes to this event each year,” Harmer told Patch. “It really is great fun, and people leave having learned something.”

The contest draws people from all over the Tri-State area, and this year, a participant traveled to Westport from Georgia to play.

“Creating experiences like these — where people can come together and have fun in such a positive way — are really important in this day and age,” Harmer said.


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