In 1936, a young entrepreneur, Paul D'Amour, aided by his brother, Gerald, and sisters, Ann Marie, Yvette, and Gertrude, purchased the Y Cash Market in the Willimansett section of Chicopee, Massachusetts, at the "Y" intersection of Chicopee and Meadow Streets.

According to Paul D’Amour on the 50th anniversary, it was in the fall of 1936 that the brothers began Y Cash Market, the forerunner of Big Y.

In July 2016, it was announced that Big Y had entered into a purchase agreement with Ahold and Delhaize Group for eight Hannaford Brothers locations in Massachusetts as part of the divestiture of stores to gain clearance from the Federal Trade Commission for the impending Ahold/Delhaize merger.

[5] The new stores, all converted from Hannaford, are located in Kingston, Quincy, Norwell, Milford, Norwood, West Peabody, Saugus, and Easton.

As of September 2023, Big Y operates 73 supermarkets in Massachusetts and Connecticut;[3] many of which are located in the metropolitan areas of Springfield, Worcester, Greater Boston, and Hartford.

Four of these stores (Branford, Mystic, Old Lyme, and West Hartford) were renovated and re-opened as Big Y World Class Markets within a short period of time.