In compliance with a New York State mandate to measure and mark its main thoroughfare, the Town of Southold set stone mile markers along the Main Road in 1828 from the town line in Laurel east to Orient Point. With one exception, all twenty four of the stones survive today, despite numerous automobile mishaps and road improvements.

To honor the Town of Southold’s 375th anniversary in 2015, the Historical Council sponsored the restoration and preservation of the mile markers by two local Eagle Scouts. The project was generously supported with a grant from the Robert D.L. Gardiner Foundation; signage at Orient Point was provided by a grant from the William G. Pomeroy Foundation. The mile markers are designated as Town of Southold landmarks and are proposed for listing on the National Register of Historic Places.