As I described in previous posts, Margaret Barrett Huntington Stoughton (1595-1665) emigrated to Massachusetts Bay Colony in 1633 with five children; she was widowed during the voyage! She re-married a man named Thomas Stoughton II (15??-1661) in late 1634 or early 1635. He had at least three children. Not soon after the marriage the Stoughton/Huntington Family moved with a group to an area on the Connecticut River called Miatianuck. The group would re-name it "Windsor."
All of Margaret's boys would leave Windsor by 1662. Step-son William headed north, perhaps as early as the late 1630s, and helped settle the towns of Salisbury and Amesbury, MA. Next, in 1647, Christopher and Simon moved to Saybrook, CT on Long Island Sound.
Finally, Thomas, her middle boy, in 1662/3 moved to ultra-conservative Branford, CT and eventually founded Newark, NJ as a conservative Congregationalist settlement.
All of these young men were following older men, into new wilderness areas so they could gain more land, wealth, and political power. This is an early example of the very movement pattern, that continued until the late 19th century, described by Jackson Turner Main in his famous "Frontier Thesis" of 1893.
It is always important to remember that these opportunities to strike out for a better life only applied to Congregationalist white men (and their families). And, that Native American's were victims of this unbridled movement. Native Americans, Black Americans, single women, and families of other religions were restricted in their ability to just up and move to a new town.
Anyway, sometime in 1647, probably the spring, Christopher and Simon set out for Saybrook, CT (on Long Island Sound and the head of the Connecticut River) with Major John Mason. Mason, was the most respected military man in New England (in spite of the fact that he led a massacre against the Pequot ten years earlier). He and the Stoughton's had become friends in Dorchester. Likewise, he and the Huntington boys would follow each other around Connecticut as they endeavored to find the best land available near navigable water.
Saybrook was not a thriving settlement and needed new families from places like Hartford and Windsor. There would have been many attractions for Christopher and Simon after a little over 10 years in Windsor: the sermons of the young Reverend James Fitch, more land, opportunities for political power, and proximity to better trading routes.
Both Christopher and Simon were given land allotments at Saybrook. Remember, every man at this point in time had several occupations. Every man had to plant crops and tend to their livestock (with the help of wives--especially with regard to milch cows). Even ministers farmed. Men had other occupations too like building furniture, shoe making, weaving, and more. Women, as is no surprise, spent most of their time within the confines of their home and yard, making and producing food from scratch, beer, and cider. There even was a fort (but it burned down late in 1647).
But Christopher and Simon were starting up their nascent merchant operation in Saybrook. A very important letter survives from the Saybrook-era that points to their Atlantic world trade. The letter is from Uncle Peter Baret (back in Norwich, England) to Christopher. It is dated 20 April 1650 and with close examination reveals a lot: that Uncle Peter knew that his niece Ann did not want to marry (she was only in her early 20s when she declared this), that there were some inheritances coming to the Stoughton/Huntington family, and that he could not guarantee them Dutch cloth! Also, that the family was active in Barbados and London--all of these clues jive with Bernard Bailyn's and Wendy Anne Warren's assertions that 17th century merchant trade, in the English colonies, depended on strong kinship ties. You could only trust family!
The Huntington boys were dependent on their mother's family, the Baret's, to offer goods in Saybrook for sale. In turn, they likely traded Connecticut commodities to Barbados--a shaky "triangle trade" was going on, and, in the midst of the English Civil Wars.
Finally, by 1653, both Christopher and Simon were married. Christopher in 1652 to Ruth Rockwell (from Dorchester and Windsor) daughter of Deacon William Rockwell. And, in October of 1653, Simon to Sarah Clarke (Newtown, Hartford, Saybrook, Norwich, Milford), daughter of prominent Saybrook land owner, John Clarke (Newtown, Hartford, Saybrook, Milford).
In the spring of 1660, Christopher, Ruth, Simon and Sarah, would lead a pack of like-minded families to a newly purchased piece of land, brokered by Mason (and others) and Chief Uncas of the Mohegans in what was to be called Norwich. The group was formidable enough for even the newly widowed Reverend James Fitch to join them. Literally, half of Saybrook up and moved to Norwich. Saybrook continued to languish as a little colony and would take years to rebound.