||Richard Stout was a New Netherland settler.|
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Circa 1604 -- Richard Stout was born at Burton Joyce Parish, Nottinghamshire, England. He was a son of John Stout  and Elizabeth Bee/Gee of Nottinghamshire, England. He died after June 9, 1703 when his will was written and before October 23, 1705 when his will was probated. In it he names his children but not his wife. Judy Jackson Scovronsky has provided an overview of Richard Stout's will.   Circa 1640 -- Richard Stout served in the English Navy, but when his term was up he got a discharge and left the ship in New Amsterdam, New Netherland. Some say he made this choice to board a ship of war because of an argument with his father over a young woman he had addressed. More about this can be found here.   
In the Spring of 1643 New Netherland Director-General Willem Kieft employed Richard Stout during a Native American uprising. On October 13, 1643 Richard Stout was at Gravesend, New Netherland when he with two others unloaded 200 pumpkins from the ship "Seven Stars" and as noted in Gravesend Town Book. 
Spring 1643 -- 1644 -- Richard Stout and widow Penelope Kent van Princis married at New Netherland. 
1644 - 1669 -- Most, if not all, of Richard's and Penelope's children were born at Gravesend, Long Island, New Netherlands. Excluding any deceased children, the birth dates and spouses of the 10 known children would be as follows:    
Sometime between 1644 and 1664 -- Richard and Penelope Kent van Princis Stout moved to what became Middletown, Monmouth County, Province of New Jersey. There is some disagreement among the following sources regarding when they arrived. One states they left as soon in 1644 as they got married,  another says they were in Gravesend in 1657, Streets suggests 1664 and Salter  claimed that the first deed for the purchase from the Indians was made in 1664. More about this may be found here.
February 20, 1646 -- Richard Stout received Lot 16 in the allotment of house lots at Middleton. October 26, 1649 -- Richard Stout sold a crop of tobacco at Gravesend, New Netherland.
In short Richard Stout had a lot in 1643, a plantation in 1657 and was the largest landowner in 1661 in Gravesend, New Amsterdam, New Netherland (now Brooklyn, Kings County, New York City, New York). Gravesend, NY was getting crowded and Richard and Penelope Stout crossed the bay to New Jersey in 1664 to take advantage of New Netherland Director-General Peter Stuyvesant's proclamation after a settlement was reached with the Indians for the purchase of the land. As one of the Monmouth Patentees he received the following: 480 acres for him, his wife and two sons, John and Richard or 120 acres each. His sons James, Peter, and daughters Mary, Alice, and Sarah each received 60 acres for a total of 300 acres.  Stillwell included the husband of Mary Bowne, James Bowne, and Alice Throckmorton, John Throckmorton with a total each of 240 acres. 
January 25, 1664 -- The Patentees purchased land from the Native American Sachem Popomora with the following: "118 fathoms seawamp, 68 fathoms of which were to be white and 50 black seawamp, 5 coats, 1 gun, l clout capp, 1 shirt, 12 lbs. tobacco, 1 anker of wine: all of which has been acknowledged as having been received: and in addition 82 fathoms of seawamp was to be paid twelve months hence." 
September 9, 1664 -- At his home in the Bouwerij, New Amsterdam, Netherland Director-General Peter Stuyvesant signed a treaty surrendering New Netherland to British Commander Colonel Richard Nicholls. Henceforth, New Netherland became New York. 
April 7, 1665 -- New York Governor Richard Nicholls approved this deed and two other deeds that followed. All of them are a matter of record in the Secretary of State's office at Albany, NY, in Lib. 3, page 1, the Proprietor's office of Perth Amboy, "also a map of the land embraced," in the Secretary of State's office in Trenton, New Jersey and New Jersey Archives, volume 1, page 44.  The first Baptist Church of New Jersey was founded in the kitchen of the Stout home. For twenty years eighteen charter members met in the home until a log church was built. A new church stands there now, but part of the original church has been preserved in it. 
Estimated birth year 1604 of Richard Stout I:
See the reference to page 295 of Stilwell's book and Streets's book page 18 cited above which says he was forty years old when he married Penelope
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