Nostrand Parkway is located on the western side of Shelter Island. It was one of the first “subdivisions” on the island, developed in the late 1800’s. The parcels are 1.5 acres and larger, with western facing views toward the North Fork and Southold. Considered a premier estate section, Nostrand Parkway has been home to luminaries, on a quiet road with old, established trees.
Bootleggers’ Alley, which intersects with Nostrand Parkway, has a Town Landing with a boat ramp and a wide sandy beach leading to Crab Creek. During the Prohibition, “rum runners” would unload their cargo on this street, where it was then hidden throughout the island. During the mid 2000’s, a treasure trove of rounded bottom glass liquor bottles were unearthed in a boat house, adding to the folklore of Bootleggers Alley.
During the early part of the 1900’s, passengers disembarked boats here and steamer trunks were loaded onto horse-drawn carts to bring to vacation homes and to hotels.