On September 18, 1837, the Shelter Island Commissioners of Highways, Purple Jennings and Jeremiah Case, proposed laying out a road from the intersection of Monroe and Eagle streets in the Village of Prospect south through the properties of Frederick Chase, B. B. Wiggins, and Esther Sarah [Nicoll] Dering to the public highway at the City, three rods wide, running a total of 214 rods and 15 links. (About fifty feet wide and two thirds of a mile long.)
So many questions. The City ? The Village of Prospect? Where are these places?
The “City” was roughly the area surrounding the stretch of West Neck Road between North Menantic and West Neck roads. There were, and still are, many houses congregated here. It was well known as the City in the 1830s.
The “Village of Prospect” is more problematic. The intersection of Monroe and Eagle streets? Ralph Duvall in his 1932 History of Shelter Island talks about Frederick Chase’s “City of Sobrie” more as if it was a dream of this very religious man, but not as a real place.
But it was a real place, described in a number of deeds as a “place called Prospect near Derring’s Harbor.” There were five streets running east to west: Washington on the north, then Adams, Jefferson, Madison and Monroe, and four streets running north and south: Cedar on the west, then Fair, Eagle, and Carbon. The lots between Washington Street and the high water mark of Greenport Harbor on the north were not quite square varying from nine rods to ten roads deep, but always nine rods wide. All the other blocks were nine rods by nine rods with four lots in each block, each block 81 square rods or about one half acre. Thirteen plots in the “place called Prospect” were sold in 1836. There were additional sales in 1838 and 1840. The block described in the 1837 minutes of the Town as the north end of the new town road, Lots 5, 6, 7, and 8 on the northwest corner of Monroe and Eagle streets, was purchased from Frederick and Rebecca Chase on May 10, 1838 by Joseph Penny of Greenport.
There is little doubt that Washington Street is the same as Summerfield Place today and Carbon Street was approximately where Clinton Avenue is today. The new highway, completed between 1837 and 1839, is New York Avenue.
There is ample evidence from the deeds and maps that there was a wharf where the North Ferry Terminal is today, called the Shelter Island Wharf.