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This is a contributing entry for Southold Town Milestone Tour and only appears as part of that tour.Learn More.

Hidden in a hedge, this milestone sits in an area of what is today northern Greenport, was once known as Stirling. It was named after William Alexander, the Earl of Stirling, who was given all of Long Island and most of the northeastern coast of North America by King Charles 1st in the 1600s.


  • Southold Town Milestone #22

Southold Town has across the length of the town a series of granite milestones. In 1829, New York State mandated that, “It shall be the duty of the commissioners of highways of each town, to cause mile-boards or stones, to be erected, where not already erected, on the post-roads, and such other public roads in their town, so they may think proper, at the distance of one mile from each other, with such fair and legible inscriptions as they may think proper.”  (New York State. The Revised Statutes of the State of New York. Albany, New York: Packard and van Benthuysen, 1829. 503)

Since Southold only had one road that ran from west to east, the stones were installed along the length of the town on what was then the King’s Highway. The miles on the stone indicated the distance between the stone and the county offices in what was then Suffolk Courthouse (Suffolk CH), now known as Riverhead. 

All of the stones were originally set up on the south side or east bound side of the road. Today the majority of the stones remain where they were originally set. While the stones are interesting in themselves – after saying that the stones are made from granite and weigh about 450 pounds each – there is not a lot to say about them.

Some of the stones sit in places that are dangerous for pedestrians and bicyclists. Please be aware of traffic! Also most of the stones are on the edge of private property, please be respectful. 

Abbott, Katharine M. Old Paths and Legends of the New England Border. New York: G.P. Putnam's Sons, 1907.

Antiquities, Society for the Preservation of Long Islands. "Building Structure Inventory Form ." Mattituck, New York, 1985.

Earle, Alice Morse. Home Life in Colonial Days. London, England: Macmillian Company, 1898.

Folk, Amy Kasuga. "Southold History/European Settlement of Southold." Southold Town Laserfiche Town Historian Folder. October 19, 2019. https://www.southoldtownny.gov/ (accessed May 17, 2020).

Kasuga Folk, Amy. Milestones of Southold Town. Lecture, Southold, New York: unpublished, 2015.

State, New York. The Revised Statutes of the State of New York. Albany, New York: Packard and van Benthuysen, 1829.

Tuthill, Seth H. "Southold Town Records, Liber E." Southold, New York: Unpublished, n.d.