This street was born Holyoke Court in 1906 on the Berkshire Hills tract. (It became a “Drive” in 1937.) There was also a Cambridge Court on the tract; it’s now part of Avenue 35. I propose that Holyoke and Cambridge, two well-known Massachusetts towns, lent their names to these streets as a tie-in with the tract’s own name: the Berkshires are a scenic range of hills and mountains in western Mass. Unfortunately I don’t know who was behind the tract. There’s a slight chance that it was Abbot Kinney, who owned hundreds of acres around here, but he had no ties to Massachusetts himself.