Maybe we need to clarify Sing Sing, NY was the official name of the town back then and it wasn't until 1901 that the name was changed to present-day Ossining, NY. Therefore, the scanned cover dated 1888 was mailed some 13 years before the town officially changed its name to Ossining, suggesting that the cover in question was mailed to/from a townsfolk and not anyone connected to or incarcerated in the prison:
Quote:
In 1813, the village of Sing Sing was incorporated, and in 1845, the New York State Legislature created a new town out of the northern part of what had been the Town of Mount Pleasant. A local Indian authority suggested the town be named Ossinsing, a different form of the name Sing Sing. One year later the last "s" was removed for ease in pronunciation. In 1881, the town considered changing its name to "Garfield Plains" to honor the recently assassinated President of the United States, James Garfield, but dropped the idea after the much larger city of White Plains in southern Westchester County objected. In 1901, to prevent confusion of goods made in the village with Sing Sing prison-made items, local officials had the village name changed to Ossining as well.