The western most milestone in the Town of Southold, the number#7 denotes that the border of Southold was seven miles from the county offices, which were located on the corner of Roanoke Avenue and West Main Street in Riverhead. The community around the stone was originally known as Franklinville, named after Benjamin Franklin, however in 1898, the hamlet petitioned to have their own post office. Unfortunately for the residents, there already was a Franklinville post office in Cattaraugus County. Having two places in New York State with the same name was already causing confusion, so the post office application was denied. The community finally got a post office after they voted to rename themselves Laurel after the lake just to the north of the Main Road.
On the eastern edge of Laurel, this milestone has been the victim of several car accidents. After being removed for many years to protect it, in 2017, the stone was conserved and re-installed. It was decided at the time in order to avoid any more damage to reset the stone several feet farther south, away from the road.
Not far from the heart of Mattituck, the view around this stone has changed considerably from when it was first installed. When it was set up the area was open farmland that stretched a short way southwards to meet up with James Creek and surprisingly, Peconic Bay, which is closer than you might think.
Just on the other side of the business area of Mattituck, milestone #10 sits across the street from the Bicentennial Farm. The land has been farmed by the same family since the American Revolution. Although it is difficult to see, milestone also is sited close to Marratooka Pond, which is located directly south of the road.
On the border between Mattituck and Cutchogue, this milestone sits above the roadway on the hillside. Please be aware of traffic and respectful of private property! It out of all the milestone is the most difficult to stop and appreciate because of its location. But it is the most lovingly cared for marker and is generally decorated for each holiday.
Located at the edge of the road between two driveways, marker #12 is just west of the lovely Italianate home built by the Osborne family in the 1850s. The home later became a parsonage for a short while for the Presbyterian Church which is located farther east down the street. Today the Osborne house is a private residence.
Once part of the Fleet estate, the marker now sits at the edge of an open field. Henry L. Fleet made good living, in the late 19th century, raising prize winning livestock and indulging in his passion for breeding racehorses. His former estate most recently has been used as a vineyard and tasting room.
This stone stand on the eastern edge of an area the locals in the late 19th century nicknamed Blubberville. The name came from a number of whaling captains, from Sag Harbor on the south fork of Long Island, who had made their fortune, retired from the sea and moved to Cutchogue to become gentlemen farmers.
The site of #15, looking south, gives a chance to see what most of Southold Town looked like for centuries. Picture the whole area as open farm fields as far as the eye could see. These lands were during the 1700’s owned by the Hutchinson and Case families. The Moses Case House which originally stood by the intersection with Peconic Lane, just to the west. The structure was moved twice to save it from the wrecking ball. It now stands on the western side of Hortons Lane in Southold.
At the western edge of the hamlet of Southold, this stone is across the street from Triangle Park. The area sits at the edge of a small hill, which dips down into the business area of the community. During the 18th and 19th centuries the windmill which ground grain and corn for the local farmers stood just east of here on the hill.
While the Southold Presbyterian Congregation is the original church founded by Reverend John Youngs and his followers in 1640, the Church just to the west and the parsonage just behind the milestone are not the original structures raised by the European settlers to this area. The parsonage was built in 1836 at the same time as the church. The church is the third structure to serve the congregation.
Today the Main Road, also known as the Kings Highway, continues eastward into Greenport. However when the milestones were set up in 1829, the Kings Highway turned north at what is today Boisseau Avenue, to go around one of the arms of Town Creek which originally stretched across the Main Road.
Perched at the western edge of Town Beach, this milestone sits along the route of Meig’s Raid. When during the American Revolution, Patriot forces from Connecticut rowed across Long Island Sound to this beach. They dragged their whale boats across the beach to Hashamomuck Pond, which is just south of the road, and continued on to Sag Harbor to disrupt and raid the British forces which had occupied Long Island.
Behind this milestone stretches the marshy land of Arshamomaque Preserve. The preserved land supports the delicate and unique marshland that was not uncommon along Long Island’s shoreline prior to the intense development of the island. During the early history of Southold this marsh was part of the area the European settlers called the Great Dismal Swamp. Unfortunately, because of the rectangular shape of the milestones people sometimes mistake them for gravestones.
Hidden behind the guardrail, milestone #21 marks the eastern edge of what was the estate of Richard Conklin. A horse breeder, Conklin was the owner of the horse, Rarus, one of the fastest trotters of the 19th century. Born in 1867, Rarus raced and broke trotting records from 1874 to 1876. In 1878 he was sold to Robert Bonner for $36,000. Rarus died in 1892 and in 1978 was elected an immortal in the Harness Racing Hall of Fame.
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.
Just east of this stone is Maple Lane, which was once the driveway of the estate of Henry Merkel, who was a businessman from Queens. Originally from Germany, Merkel and his brothers started a butcher’s store, which eventually spun into 43 stores spread across Queens and Brooklyn. Looking to get away from work, Merkel purchased a summer estate with 1,200 feet of shoreline on Peconic Bay. Being thrifty he wanted the property to pay for itself; so he established a dairy farm on the estate.
Located in the center of East Marion, the house behind this milestone is unusual in that the 2nd floor of the home used to be the East Marion School house. When the community needed a larger building to accommodate students, the old school was moved across the street. It was lifted into the air and the first floor was built under it.
This milestone is located on the north side of the roadway. When the road for the causeway was being built and expanded, the construction crews not knowing what the milestone was, uprooted and pushed it aside. One of the residents realized that if he didn’t work quickly a piece of history was about to be lost. He rescued the stone and had it set up on his property facing the spot where it originally stood.
Standing by the western edge of Orient Village, of all the milestones, this one as the best view! The farm on the south side of the road is the former Dyer farm. The farm originally extended to both sides of the road and locally the farm house was known as the House of the Seven Gables. The house was destroyed during the 1938 hurricane.
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Southold Town has across the length of the town granite milestones. For many years, a legend about the markers was widely and enthusiastically, believed to be the history of the stones. The story was that Benjamin Franklin came to Southold, in 1755, and personally set up (or over saw) the installation of the milestones. If you don’t see the milestone right away in the google map picture try rotating the view!
