So that is probably how early we can officially go. But chess was played in the Boylston Chess Club space in the YMCU on Boyslton Street for many years before the founding of the club. How early can we go?
YMCU on Boylston photo-1911
What I like about this reference is that chess is not mentioned in the 1867 or 1868 yearbooks, giving me confidence I'm hitting one of the earliest references to the chess of the future Boylston club. Not a spectacular mention, but one that suggests chess was played at the YMCU 50 years before the club was officially founded.
So, with that I turn it over to the club elders, who may have more details about the club's early days. During my library work, I barely touched the old newspaper clippings and other dusty materials that may hold even better information. What I would really like to see are some early cross-tables, perhaps even those from unofficial tournaments BEFORE 1919. That would be pretty cool.
But I also hope that other club members will dive into the great Google Book resource and find even more print references to chess in Boston.