This is an imaginary conversation with a member of a ‘first’ family whose roots in Southold Town — which originally included present-day Riverhead — date back to the town’s founding in 1640. The history reflected in the answers comes from Southold and Shelter Island town archives, records and other sources.
Q: For generations, Southold and Southampton have been going back and forth in a debate over which town was settled first. What is the answer?
A: Well, let’s be clear: The Indians were here for thousands of years all by themselves. End of story.
Q: OK, fine. But who was first?
A: See previous answer.
Q: Can you perhaps offer a bit more? It’s important to me. My family line here goes back to the 1600s.
A: There are clues as to whether the North Fork or South Fork was settled first by white people. An educated guess based on available clues can be arrived at. But the difference between a formal white settlement in one town versus the other is probably just a matter of weeks. It is meaningless to keep up this discussion. And keep in mind that some things long thought to be true have, on closer inspection, turned out to not be true.
Q: Surprise me.
A: The Cutchogue-New Suffolk Historical Council had the beams in the Old House on the Village Green tested and the wood cores came back to 1699. Not within a few years of the supposed date in 1640 when English people came over from Connecticut — but well past that. Its long billing as the oldest English-built house in New York State is not true. That’s not town history, of course, and it’s just one house, but the importance of this discovery is not to be downplayed. That house was probably first occupied in 1699 by one Joseph Wickham, who had come to Cutchogue from Southampton.
As for which town was settled by Europeans first, does it really matter? If you can’t go to sleep tonight until you know the answer, consider this: There is some evidence that in 1636-37 a group of some sort was at Hashamomuck tapping pine trees for resin used in boat caulking. They surely weren’t the only such crews on eastern Long Island, nor were they a formal settlement. European fishermen — Portuguese, Basque and probably others — were fishing the northeast Atlantic coastline for cod well back into the 1500s and perhaps before Columbus, whose “discovery” in 1492 has been overblown. And, of course, there were Vikings in Canada in the year 1000. You don’t think they ventured south?
Q: Hold on! I’ve read for years the saga of Southold’s settlement and the story of the Old House. I’ve read the brochure! I saw the historical marker! I took my kids there! You’re telling me that story is not true?
A: Indeed. Some of the early history written here was little more than cheerleading. There is a big difference between cheerleading and patting yourself on the back because someone from your line was here “first,” and real history based on archives, primary sources and, for that matter, science. Dendrochronology — wood core testing and dating — is real science.
Q: I will continue to believe what I want to believe. My people were here first!
A: Good luck with that. But while I have your attention, this is the settlement story line as it is accepted today: A group from the Massachusetts Bay Colony sailed south in February 1639. They went to Oyster Bay first, where they were expelled. They then turned east and sailed into Peconic Bay around June 1640. (This was the Julian calendar, with the new year starting in March.) They landed at North Sea and headed south to a site where Southampton Hospital is today. They were likely the first formal English settlement in either town. Another point to keep in mind: Lion Gardiner was already living on his island in the bay to the east when these folks arrived. In terms of English settlement on the East End, he was first.
Q: What about Southold?
A: Well, first, don’t read anything by a certain early Southold “historian” who shall remain nameless here. The words “invented out of whole cloth” describe his work. But a good guess is that a religious-inspired group came here from Connecticut as part of a venture called the New Haven Colony. It would have been in 1640, too, perhaps just after the Lynn, Mass., group. Logic says they would have come early in the growing season so they could get a crop in the ground and thus have something to eat.
Amy Folk, the accomplished Southold Town historian, points out that records show the Rev. John Youngs, the group’s minister and organizer, was still in Massachusetts as of May 1640. That would move the group he brought to Southold to weeks or months after that and probably into the fall. Those first settlers here lived in makeshift houses. The time difference between when either group landed is insignificant. History isn’t a competition.
Back to the Old House in Cutchogue: It is too fancy for a first-generation house. That house was built in the second or third generation by people who were settled and successful and had money and slaves — and after the Indians had been herded onto smaller tracts of land and were out of the way. But don’t weep for the Old House. It’s still a grand home and a wonderful part of Southold history.
Q: What was the relationship between those first English settlers and the Indians, in New England and here?
A: See: history of Ireland.
Q: Oh. OK. Not good.
A: Indeed. To the English, the Indians were in the way of their dreams of landowning gentility and being lords of their own manor — something they couldn’t possibly be in Old England, where they didn’t want to be because this or that person was Catholic or the wrong kind of Protestant. And where some of the locals didn’t want them around either, or they were just the wrong class in a class-saturated society. Think Downton Abbey rolled back a few centuries. So they came here, where they could be in charge and make everyone around them be just like them. Exactly what they didn’t like in the Old Country.
Q: What about Shelter Island?
A: Shelter Island was included in a 1620 land grant by England’s King James I, but no Europeans were formally living there until after William Alexander took possession in the late 1630s. From Alexander the island went to one James Farret and from him to Stephen Goodyear of the New Haven Colony.
Goodyear sold the island in 1641 to some Barbados sugar merchants, one of whom was Nathaniel Sylvester, who was likely the island’s first white settler. In 1652 he made the purchase legal, in his eyes, through an agreement with a Manhanset Indian named Youghco. That year he built a house on the island and a fully developed plantation was soon up and running, complete with scores of enslaved Africans and American Indians. The Sylvesters also gave shelter to Quakers.