This month, The Westport Library will host their 27th annual Crossword Puzzle Competition. While the event might not be as well-known in town as some of their tentpole events like VersoFest and BOOKED for the Evening, the contest is an annual gathering of some of the most die-hard competitive puzzlers, who come together on one of their favorite days of the year. And it can be traced back to one fateful meeting between The Westport Library’s former director and Will Shortz.
For the uninitiated, Shortz is a revered figure in crossword-puzzling; since 1993 he has served as the crossword editor of The New York Times and has been featured as a recognizable face of crosswording in cameos on shows like How I Met Your Mother, Brooklyn Nine-Nine, and The Simpsons, among others. Back in 1998, the then-director of The Westport Library, Maxine Bleiweis, happened to meet Shortz in N.Y.C. while he was autographing crosswords at the “New York is Book Country” street fair. Bleiweis, newly arrived in her role and looking to bring a crossword puzzle contest to Westport after finding success with them at other libraries, took her moment with Shortz to ask if he might share an unpublished crossword of his to use at the event. “He surprised me by saying ‘Could I come and conduct the contest?’” Bleiweis recalls. “I immediately said yes.”
Shortz’s presence gave the Westport contest a major visibility boost. Other than the contest Shortz runs himself, the American Crossword Puzzle Tournament (which, coincidentally, is usually held in Stamford), ours is the only other one he attends. “I've been to almost every one since the second one,” Shortz tells Westport Lifestyle. “After I went once, I was so impressed with the library, and liked the people, and it's just a good time.” At the contest, competitors complete three 15-by-15 crossword grids as quickly as possible, in a series of rounds. The final round, the playoffs, happens on stage, and there are also awards for “best penmanship” (in both ink and pencil), so less speedy attendees can still earn recognition. While judges score the rounds, Shortz plays word games with the crowd. “In my job as a crossword editor, I send my stuff out into the world, and I have to wait weeks or months to get a response from the audience,” Shortz says. “The wonderful thing about the Westport tournament is that I'm with the puzzle solvers, and get to hear their responses.”
For avid puzzlers, the contest has become a highlight of the year, bringing together a real community around a favorite hobby. And Shortz’s involvement has kept energy around the competition high. “The fact that he continues to want to come every year is fabulous,” says Jennifer Keller, the senior programming and events coordinator for The Westport Library. “He really makes it special.” Bleiweis agrees. “It became known as the ‘warm-up’ for [Shortz’s] big annual contest in Stamford,” she says. Westport, with its early-in-the-year timeslot, carved out a niche in the puzzling community. “There’s a whole world of competitive crossword puzzle tournaments,” explains Quiara Vasquez, the crossword editor at Slate and the current reigning champion of Westport’s contest. And while ours may not be one of the highest-profile ones, it has a reputation of being convivial and fun. Friendships have been forged wholly because of the contest. Stacy Stableford, a retired Westport school teacher, has been competing for more than 20 of the contest’s 27 years, and has a circle of friends she calls her “same time next year club” because they reunite each February at the contest. “We pick up as if a year has not gone by,” Stacy says. “We know each other's kids, and who's got [grand]babies, and it's just a lot of fun.” Stacy's husband, Lloyd Stableford also a retired teacher, competed once, but found more enjoyment as a volunteer scorecard runner. He loves the chance encounters with parents of his former students who are competing, he says, “and talking to Will [Shortz],” he says. “He talks to everybody, he’s very personable. It’s a lot of fun.” (Volunteers are always needed!)
One of the unique aspects of our puzzle contest is that, despite its pedigree in Shortz, there’s room for casual competitors alongside top-ranked ones. “I’m not doing [crosswords] to be an expert or to be fast,” says Stacy (who has won Best Handwriting). “I savor words.” But you’ll also find some of the quickest puzzlers in the country, most likely up on stage in the Trefz Forum during the final round. Vasquez has finished a 15-by-15 grid in as little as 90 seconds. Her top tips for speed? “Look at clues as quickly as you can,” she says. When a puzzle has a series of clues that lead to an overarching theme or a sort of punchline, she says, “I try to spoil that for myself as quickly as possible. And the real trick you have to get good at is reading the clues while you’re writing in entries.”(She also learned early on in her competing days that a lowercase “e” is faster to write than an uppercase one. The more you know!)
Keller says they anticipate nearly 200 people will attend the contest this year (spectators are allowed, but only for the final round). “There is a camaraderie among the people who come to us,” she says. There’s just something about the Westport contest. “I am so impressed with the Westport Library,” Shortz agrees. “I like libraries in general, but the Westport one is special. And I think Westport has an extraordinary community as well.” So if you’re looking for something different to do this month with a great crowd—as Shortz puts it, “crossword people tend to be smart, interesting, funny, well-rounded people”—consider joining for the finals. “I just love solving crosswords,” says Vasquez. “There’s something auteurist about it. It’s a very real chance to glimpse into another person’s mind.”
The Crossword Puzzle Contest is on February 7 from 1:00 pm - 4:30 pm at the Westport Library. For registration and more information, visit westportlibrary.org