The Boylston Chess Club of the Boylston Chess Foundation is the largest chess club in Boston, and the second oldest chess organization in the United States. Starting in the 1850s the Boston Young Men's Christian Union (YMCU) maintained a small room for chess; John F. Barry, Harry Nelson Pillsbury, C.F. Burille, Franklin K. Young and Walcott frequented it in the 1890s.

The club was formally organized on August 27, 1919 at the YMCU. There were 22 charter members, and Augustus Seaver was elected as the first Club President. In its history, many leading chess figures have been Club President, including Master Emeritus Harry Lyman. In 1945, the club received charter number 51 from the newly formed United States Chess Federation.

The Boylston Chess Foundation - the 501(c)(3) organization that operates the Club - was founded in 2005. In 2022, the Club purchased and renovated the space in which it currently resides, at 35 Kingston Street #1 in Boston.

The Boylston Chess Club and Foundation is not just a historic club from the 19th century, but also a flourishing chess center in 21st century Boston, and one of the most active clubs in the nation. Since 1991, the Boylston has organized more than over 2400 rated chess tournaments. In 2022, 491 different players played in 113 tournaments hosted at the club. Throughout 2022 we had 307 different people as members. In 2022, 24 chess masters and 45 experts played in events.