What could ucalegon, Boggle and the Pleasantville Diner possibly have in common?

These are some of Will Shortz’s favorite things—favorite word, board game and local dining choice, respectively.

Shortz is the editor of the New York Times crossword puzzle, author of top-selling Sudoku books and a 24-year veteran of National Public Radio (NPR)’s Weekend Edition.

Did we mention that he was also the founder of the American Crossword Puzzle Tournament that started in 1978, and featured in the award-winning documentary Wordplay?

Shortz has been a resident of Pleasantville for more than 17 years—and he does a lot more than puzzling. In fact, he is planning to open a table tennis club in the village in about a month.

Shortz had been living in an apartment in Forest Hills for several years, forced out simply by the need for more room. In 1993, after looking at several towns and villages, Shortz settled in Pleasantville. Appreciative of “old stuff,” Shortz was drawn to his house, and the village, for many reasons.

“Pleasantville is a walking village and close to the city,” said Shortz, but, “the icing on the cake was the black and white tile in the bathroom,” reminiscent of—you guessed it—a crossword puzzle. 

Favorite haunts include the Jacob Burns Film Center and the Pleasantville Diner, the latter to which Shortz’s out of town visitors are often taken. In fact, one friend in particular, from Holland, is so enamored with the Pleasantville Diner that he has gone so far as to declare it is his favorite dining spot in the country. Nearby Quaker Hill Tavern on Chappaqua tops the list, as well.

Perhaps many of us know Shortz was an enigmatology (the study of puzzles) major at Indiana University, but he professed puzzling as a possible profession much earlier. Evidently, as early as eighth grade when Shortz declared, in a homework assignment, his intent on being a puzzle maker.

The reaction at home was mixed.

“My dad, who’s a serious guy and was a personnel director for a printing company, said, ‘Puzzles will make a great avocation, not a vocation,’” Shortz said. “He thought the dream of being a puzzler was fine, just something that would come and go—[that] it would be my lifetime hobby.”

Mom’s reaction was slightly different.

“My mom was a writer, a more creative type,” Shortz said. “She was actually the person who helped me with my first submissions to magazines. She did this all the time for her own articles, so she showed me how to submit puzzles for publication.”

He added, “She was not a puzzler particularly—she did them out of motherly love."

In fact, the pair had an agreement.

“We had this arrangement that I would read her articles if she would solve my puzzles,” Shortz explained.

Shortz’s interest in crosswords, per se, came later on.

“Novelties, new things that twist your brain in a new way,” he said of his initial attraction. “Also, the old style crosswords were not that interesting. I think I've helped make them more interesting.”

Shortz, who receives upwards of 100 puzzle submissions weekly, enjoys puzzling himself, with cryptic crosswords–in the British style as a favorite.

“I like American-style crosswords of the Friday and Saturday New York Times level,” he revealed. “Sudoku is pretty good, I like that, but I actually like KenKens better.”

But Shortz is up to a lot more than puzzling. Not only will he be doing the publicity for an upcoming British “treasure hunt” book this fall, Shortz will be opening a table tennis club in Pleasantville.

An avid table tennis player, he has been playing for years. But, apparently his club had outgrown its current facilities. Good friend, coach and table tennis champion Robert Roberts suggested purchasing club space to Shortz several years ago. Initially wary of such a project—primarily due to Westchester real estate prices—Shortz eventually became aware of potential space availability in Pleasantville...and took action.

The club, open to all, will have 13,000 square feet of space and 18 tables, making it the largest table tennis club in the northeast. Open seven days a week, memberships for children and adults will have low introductory rates, said Shortz.

Alternatively, people will also be able to pay daily, just to try it out. There are plans for after-school programs for kids, beginners’ and league nights, coaching, group lessons and monthly tournaments—with plenty of room for spectators.

The club will have staged openings, beginning with an existing club member opening in late April, followed by a Pleasantville resident opening, and culminating with a final opening for the general public. Expect Susan Sarandon—who co-owns the Spin Table Tennis Club in Manhattan—to be in attendance.

Excited about the opening, Shortz was quick to add he “really enjoys the social nature” of the club, which offers players the opportunity to play many different people.

“It’s a very friendly club, very democratic—everybody plays everyone else,” he said.

Those who worry that table tennis may trump puzzling shouldn’t. Shortz isn’t leaving anytime soon, he reassured.

And when asked if he was still excited editing the Times’ puzzles he responded, “Yes, it’s been 17 and a half years…I will never get tired of this.”