John Endicott (Endecott) purported to have been born in Dorchester, Dorset in 1588. He referred to himself as Captain Endicott and, therefore is presumed to have seen service in the English Army. Most of what is known about John Endicott’s origins is at best circumstantial. Biographers of the 19th century believed he was from the Dorset town of Dorchester because of his significant later association with people from that place. However, there is no record of him having lived there. The Reverend John White, the ‘Patriarch’ of Dorchester and Rector of Holy Trinity Church, had no prior knowledge of him. Other researchers suggest he was born in Chagford in Devon.

While resident In London, he married Anne Gower. They had no children. She was the cousin of Matthew Craddock, later Governor of the Massachusetts Bay Company, the successor of the New England Company, established to continue support for the settlement in Naumkeag (now Salem).

The New England Company planned to send more settlers and a Governor to Naumkeag to replace Roger Conant. Endicott’s name was put forward as a likely candidate for that position, presumably through his connection to Matthew Craddock. He had a reputation for being a former soldier, headstrong, opinionated and a Puritan. He was also keen to emigrate. He was appointed and sailed with his wife and a number of new settlers on the Abigail to Naumkeag in 1628.