No. 12 Gay Street (left, with lantern), ca. 1975. The Federal style row houses at Nos. 12 and 14 were built in 1827-1828 by the developers Daniel H. Weed and Joseph D. Baldwin. During prohibition, No. 12 allegedly housed a speakeasy before becoming a different sort of clandestine meeting place: the house was purchased by the married Mayor Jimmy Walker, to be used for barely-secret assignations with Betty Compton, his showgirl girlfriend.

Nos. 14-16 Gay Street, October 16, 1937. The provenance of the Gay Street name is unclear, but the name is mentioned in records as early as 1827 before the street was declared official in 1833. No 16 (right) was built for merchant Francis Barretto in 1828. No. 14 was built around the same time for plough manufacturer Curtis Hitchcock. Ruth McKenney published a series of stories in the New Yorker depicting her family’s life in the basement apartment of 14 Gay Street. These stories would be adapted into a 1953 Broadway musical, “Wonderful Town.”