Originally from an area near London, Samuel Webb came to Windham with his family in the mid-1700s where he built a house on one of his 100-acre lots in South Windham. He owned 300 acres. After staying here about 20 years, he moved to Deer Isle with his wife and son, Seth. He had 12 children altogether, most of them settling in Windham, Westbrook and nearby towns.

Historians differ on just what Sam Webb did to earn a living – some say he was the first school teacher in the settlement, but this has not been proved. His ancestral background recorded by a grandson and preserved for all to read.

Samuel Webb’s father, also named Samuel, was the owner of a slave ship. A long letter, handwritten by the ship-owner’s great grandson Seth Webb, is among the treasures in the Maine Historical Society collection. This multi-page letter tells the story of Samuel Webb who in the late 1600s lived on an estate in Redrift, near London with his wife and three children: Susanna, Samuel and Margaret.

In 1708 he set sail from London on his way to Africa to purchase slaves from a tribal chief he knew and had dealt with for years. These people had been captured in some inter-tribal battle. The Englishmen were invited to visit and have dinner at the African chief’s home. So all Webb’s crew, except four men and four boys (of which his 7-year-old son Samuel was one) went ashore where they enjoyed a meal and returned to the ship. Not a day later, all those who had eaten at the African chief’s home, had died from being poisoned.

The remaining crew of four men and four boys somehow navigated back toward England where the ship was sold and the children put under guardianship and attended school until they were of age. Young Samuel Webb, born in 1696, stayed in school until 1711, the memory of his father’s tragic death a reminder of his past.

In 1711, he left with other emigrants on board a ship headed for Newport, R.I. The trip to America was beset by a pirate ship, very common in those days, but eventually arrived safely. Young Samuel Webb, broke and among strangers, bound himself out to a blacksmith named McIntyre, learned the trade and married Mary McIntyre on Christmas Day, 1718. She died four years later leaving two sons, and he married a widow who, it is said, was a wife, mother and widow before reaching the age of 16.