The Stillwell Family
After he arrived in Virginia in 1638, Nicholas Stillwell acquired a modest piece of land and then a larger tract on the York River. He became a pioneer tobacco farmer and was named a tobacco inspector. He was also drawn into the local militia and attained the rank of lieutenant. He took part in a number of campaigns against Native Americans and was recorded as “Valiant Stillwell.” However, when Nicholas supported his commanding officer in resisting the transfer from Virginia to Maryland of Kent Island in the Chesapeake Bay—where both men were involved with a trading post—he found himself in trouble with the colonial authorities.
Consequently, in 1645, Nicholas sailed north to the port of New Amsterdam, at the time under the control of the Dutch West Indies Company. He was soon able to obtain a grant of land in Gravesend, in the southwestern section of Brooklyn bordering on the Outer Bay. He established a pioneer farm and with his English wife, Anne, raised eleven children. Nicholas also became a magistrate, again joined the militia, and fought Native Americans in the Hudson River Valley. He supported the Dutch, who had given him settlement opportunities and advancement, against the English takeover in 1664. When the Dutch lost the colony, Nicholas adapted to the new authorities in New York, obtained a larger tract of land on Staten Island, and moved his family there. The children of Nicholas and Anne settled on Staten Island and Long Island and in Monmouth and Cape May counties in New Jersey.
Their oldest son, Richard Stillwell (Theodosia's great-grandfather), was born between 1633 and 1638. Like his parents, he had a farm first in Gravesend and then on Staten Island. He was also a magistrate and held various court positions; he was a captain in the militia; and he served as an arbitrator in municipal boundary disputes and as an interpreter and intermediary in dealing with Native Americans. He married Mary Cook, the daughter of another magistrate in Gravesend. With her (and possibly with a second wife), he had fifteen children. He died in 1688.
Richard and Mary (Cook) Stillwell's second son, who was named Richard for his father, was born in 1672. He became an affluent merchant in New York City; he was also one of the founders and an important supporter of the Presbyterian Church in Manhattan. He married Lydia Bowne of Gravesend, but she died before they had children. Richard then married Mercy Sands around 1708. Mercy, born in 1693, belonged to a very well-to-do family from Long Island.
Theodosia’s mother, Ann (born circa 1714), was the third child of Richard and Mercy (Sands) Stillwell. Her brothers and sisters would do well. One brother became a doctor, and one became a merchant; two sisters married British officers, one of whom became a general and both of whom had wealth and standing. Two other sisters married well-to-do merchants, and one married a noted Presbyterian minister who had been educated at Harvard.
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