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Where to play chess in Boston: 4 places to deliver checkmate around town

A typical afternoon of speed chess and trash talk outside Harvard Square's Pavement Coffeehouse.Photo by Sam Trottenberg

It’s time to dust off the discarded tennis racket, dig through the closet for a forgotten Tommy Bahama shirt, and say “hello, old friend” to the summertime blues. While far from the most physical activity (although a three-minute blitz game is sure to get your heart rate up), chess is a fine addition to your repertoire of sunny, by-the-river or in-the-park activities.

The game has exploded in popularity over the past few years with help from 2020′s record-breaking Netflix miniseries “The Queen’s Gambit” (or as I like to call it: 1.d4 d5 2.c4) and the streaming Internet celebrity tournament series “PogChamps.” Board and accessory sales skyrocketed throughout the pandemic, grandmasters are now livestreaming for fans on Twitch, and it looks like the uptick in popularity isn’t just a fad: Free online game site reported 5.3 million new users in the last quarter of 2021 alone. If you’re dying to show off your vicious Stafford Gambit prep, or your tactical mastery, or just your love of the game, here are four places in the Boston area where you can play chess.


Harvard Square

This is the battleground. On any given day outside Harvard Square’s Pavement Coffeehouse you can find an array of chess tables armed with the grizzled hustlers who for many years have acted as a litmus test for New England’s up-and-coming players. It’s fun enough just to watch the trash talk from the sidelines, but nothing compares to the rush of playing these speed demons, and inevitably losing a few bucks. The scene has existed for decades, and remains the Union Square Park of the Massachusetts chess world. Plus, you always have the option of hopping over to Leavitt & Peirce to shop for nice boards and play a couple of games upstairs for $2 an hour. 1350 Massachusetts Ave., Cambridge.


Boylston Chess Club

Tired of losing to the savants in Harvard Square? If you’re looking to get serious, then head to the Boylston Chess Club. The largest chess club in Boston, the Boylston Chess Club was founded in 1919, though its roots trace back to the 1850s, according to the club’s website. Over the years, the club has seen top players such as Harry Nelson Pillsbury (though before it was officially founded), grandmaster Larry Christiansen, and international master Carissa Yip, the current US women’s chess champion.

“The fact that there is a full-time club that’s open all the time in a dedicated chess space makes a big difference,” said Andrew Hoy, the president of the Boylston Chess Club. Massachusetts is “not quite at the level of New York or St. Louis … but behind those I would say it’s certainly very close.”

The Boylston Chess Club hosts tournaments and events multiple times a week, both in person and online, along with occasional lectures to help you along your chess journey. 40 Norris St., Cambridge.

Jamaica Plain Chess Club

Founded just under a year ago, the Jamaica Plain Chess Club bounced around for a while before finding a home outside Jamaica Plain’s J.P. Licks last October. You can catch the group there every Thursday evening, for casual games and tournaments of several time controls. The club is free to join, and they welcome players of any level.


“We’re more like coffeehouse chess,” said founder Jamie Williams. “It’s not just the chess game itself. For us, JP Chess is about connecting people in the community.” 659 Centre St.

Medford Chess Club

Every Saturday afternoon, you can find the Medford Chess Club gathered outside Riverside Plaza playing games at the plaza’s two built-in chess tables and the 10 or so sets the club brings along. If you’re looking for some exercise, try playing a game on their giant chess set with a fast time control; you’re sure to get a workout in.

“It’s a very inclusive, all-ages, welcoming group,” said Chris Donovan, one of the club’s organizers. “You never know who you’re going to run into.”

Much like the Jamaica Plain Chess Club, the Medford Chess Club is free to attend. The group also occasionally offers events like simultaneous exhibitions, Donovan said. Riverside Avenue and River Street, Medford.

Sam Trottenberg can be reached at