Second House Museum
By Henry Osmers, Montauk Historical Society Historian
Second House is the oldest structure in Montauk. Originally built in 1746, additions to the dwelling were made in 1797 when according to East Hampton Town Trustee records, the Town allotted “three gallons of rum to raise the house at the Fort Pond.”
In those days Montauk was used solely as pastureland, a custom that dated back to the 1660s. To handle and coordinate the vast quantities of cattle and sheep grazing upon the Montauk hills, three dwellings were built to house shepherds. First House, built in 1744 and rebuilt in 1798, was home to the keeper who entered the earmarks of the animals on the Common Pasture list and made certain that fences were in good repair. He also kept a watchful eye on the sheep grazing between First House and Second House. Located within the boundaries of present Hither Hills State Park near the western border of Montauk, the house burned down in the spring of 1909.
The keeper of Second House was responsible for tending the sheep to the west and the cattle to the east, making sure there were no crossovers. Third House, located two miles west of Montauk Point, was built in 1747 and replaced in 1806. Its keeper was responsible for the entire pasture and oversaw the annual roundup each year around May 1st when the cattle would be paraded from points west to Indian Fields. He also maintained the Fatting Field list, and in the summer would ride among the cattle to see that they were grazing in their proper fields. On November 1st the cattle would be driven up, back to their farms for the winter months.