Samuel Gaines was apprenticed to Nathaniel Handforth of Lynn MA, and his term expired in 1659 or 1660. He learned to read and write and to conduct a farm. No other trade is mentioned.
About 1669 a list or census of the householders in Hartford, Windsor and Wethersfield was made, including the name of the head of the family, the number of persons in the family, and the amount of corn and grain that each possessed. It is the earliest extant census of the river towns. The names of Thomas Burnhan (Samuel's father-in-law) and Samuel Gaines appear, but the number of persons in their families and the amount of grains are not given.
Samuel and his wife Anna attended the services of the First Church in Hartford, of which the meeting house was four or five miles from their home, but the only one accessable to them. In her will, Anna Gaines states, "for love and affection I do convey to my son Daniel Gaines land I had from my father, Thomas Burnham, bounded north on the line between Windsor and Hartford, east of the Connecticut River". 2 Feb 1716