I have advanced the theory that Samuel Dayton was, for a time, in professions that took him to many harbors along both sides of the sound, the forks and ocean coast of Long Island, and perhaps to neighboring states. I believe that a young Sam may have received on-the-job training on the west end, freighting and later whaling for John Ogden at North Sea and may have participated with John Underhill in both lawful and questionable confiscations of Dutch vessels. I also believe that Sam continued ferrying and freighting as evidenced by his extended absences and his frequenting multiple ports before he finally settled down at Setauket and then at Dayton’s Neck.
It might be that Samuel’s sons also acquired Sam’s fondness for adventure in distant waters as we learn that his fourth son Isaac Dayton was employed by Abram Smith before becoming his partner in freighting with Smith’s boat. The language of their agreement clearly indicates Smith’s confidence in Isaac’s ability to operate and be responsible for the transportation of people and cargo.
It is known that third son Abraham Dayton had a whaling company, at least for a short time.
It is even possible that second-born son Samuel was following his father’s profession when he was drowned while hauling ground grain from Milford CT to Port Jefferson Harbor.
To be continued…