Caleb Littlefield was born about September 4, 1659 Wells, York Co., ME[1][2]
As a youth he was apprenticed to Nehemiah Partridge of Portsmouth, N.H., and became involved in a love scrape with a girl named Mary Allen (N.H. Court Files at State House, Concord, N.H.)..[3] Thereupon he left Portsmouth and next appears in Weymouth, Mass., where he was warned out in 1686. He came to Braintree with his brother Edmund at the time of the Indian Wars in Maine near 1688. They removed to Block Island, R.I. & Kingston, R.I. Caleb Littlefield at 30 deposed Jan. 21,1690/1 (Mass. Archives 36-313 a.) He was taxed in Braintree May 1,1690 in "a country rate" made by the selectmen. In 1692 he was living in Braintree, where his brother Edmund had settled, and his eldest son, Caleb, was born there in July 1692.
Samuel married Lydia Mott, sister of his brother Edmund's wife before 1692 at Braintree MA.[4][5] From this time, until 18 Marc 1713/14, we lose track of him, but on that date he was living at Kingstown, R.I., when the town of Wells granted to him and other Rhode Island men 100 acres apiece on the Mousam River (now in Kennebunk) (Well Town Grants). Soon after in 1714/15 he settled on Block Island.
On 1 May 1714, Caleb Littlefield of Kingstown, R.I., bought land at the Island from John Sands and removed before 6 June 1715, when, in a deed, he purchased more land from John Sands, he is referred to as "of New Shoreham", Caleb was the ancestor of the very numerous and prominent Littlefield family on Block Island.
Caleb died at Block Island, before 5 march 1743/4, leaving three sons, Caleb, Samuel, and Nathaniel, and several daughters. [6][7]
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