Old Town Roads Described

Footnotes to Long Island History

Old Town Roads Described


Thomas R. Bayles


          An interesting legend has been handed down regarding the Whiskey road. The story goes that in early years, one of the Randall family that lived on the farm of the late John G. Randall in the northern part of Ridge, had a girl friend by the name of Swezey, who lived in Swezeytown, north of Middle Island, and near where the Whiskey road comes out. In those days, farmers had slaves. They were ordered to clear a trail from the Randall farm to the Swezey farm, and as an incentive for the men to work, a jug of whiskey was set ahead some distance. The slaves were told that when they had the road cleared to the jug they could have a drink. Then the jug was set ahead again and each time the course was changed which is supposed to be the reason why the road is so crooked, and why it was given its name, Whiskey road.

            The old Hay road which ran across the Island to Mastic was an important road in the years gone by. The northern entrance to Camp Upton followed this road from the Middle Country road south. The farmers used this road to go to the salt meadows around Mastic where they cut salt hay and hauled it to their farms in the middle and north side of the Island.

            At a meeting of the Town Trustees in 1704 it was decided that the residents should engage in the work of clearing the highways, according to the orders given by Thomas Helme, one of the commissioners of the county for laying out highways. The people of the town were to work according to their assessments in the county rate. The following year the town ordered that men should be sent four days a year to clear the commons and repair the highways. In August of that year men went to clear the Middle Country road, one gang going east to “Horn Tavern,” and the other west to the Smithtown line. In 1707 it was ordered that every freeholder should work two days in clearing the commons and highways of brush and undergrowth.

            The oldest road of any great length opened in the town is that running from Setauket in a south-easterly direction through Coram to Fireplace  (South Haven), called the Old Town road. It was opened soon after the town was settled and was the main thoroughfare of travel from the town capitol at Setauket to the settlement at Mastic and the meadows. For many years it was used more than any other long road in the town.

            Roads were also opened at an early date from Setauket east to Wading River, and west to Smithtown. The Old Country road through the middle of the Island, now Middle Country road, was broken through shortly before 1700, and the roads parallel to it on the north and south sides of the town were opened shortly after.

            A road laid out from Old Man’s (Mt. Sinai) south was laid out in 1728, and another from Old Man’s to Wading River at the same time. Some of the roads laid out in the 1700’s include: The Horseblock road, running from Southaven to Stony Brook in a northwesterly direction: the Sill’s road, running from Bellport to Swezey’s Mill in Yaphank; a road southerly from Coram to Patchogue; another from Halsey’s Manor and Brookfield southwest to Fireplace Mills ; the “Wading River Hollow road” from Woodville  (Shoreham to Middle Island; a road from Yaphank to Moriches; another from Miller Place to Middle Island, then following the bank of the Connecticut (Carman’s) river through Yaphank and to Mastic; the “Granny road” running from a point south of Middle Island westerly to a junction with Horseblock road. Another was the “Crystal Brook  Hollow road,” from the west part of Old Man’s to Coram in a southwesterly direction. The road from Coram to Drown Meadow (Port Jefferson) was laid out in 1790.

            In 1712 a road was laid out “between John Roberson’s land and Samuel Dayton’s Lande to ye olde mans Beach a hiwaye layde oute tu Rod wide, a swinging gate allowed.”

            The commissioners of highways divided the town into 40 road districts in 1830.

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