The Boylston Chess Club of the Boylston Chess Foundation is the largest chess club in Boston, and the third 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.

In 1989, facing sharply increased rent and deteriorating facilities, the Boylston Chess Club moved to the 8th floor of the YWCA at 140 Clarendon St. in Boston. The club was incorporated as a Massachusetts non-profit corporation in 1995. In December 2003, the YWCA's building renovation plans forced the club to move to a new home in Davis Square, Somerville.

The Boylston Chess Foundation -- the 501(c)(3) organization -- was founded in 2005.

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 1750 rated chess tournaments. In 2015, 307 different players played in 72 tournaments. At the end of 2015 we had 233 members, and throughout 2015 we had 258 different people as members. Members and players at the Club in 2015 included 27 chess masters and 27 experts.