Little is known of the family's activities during the Middle Ages aside from Sir Otho Gilbert of Compton serving as High Sheriff of Devon from 1475 to 1476.
It was descendants of this Otho Gilbert who would set out during the Elizabethan period on the family's “hereditary scheme of peopling America with Englishmen”.
Their lesser-known brother, Sir Adrian Gilbert of Compton, was nonetheless of the same cloth, having an especially savage military reputation in Ireland while also seeking a Northwest Passage to China under a patent from Queen Elizabeth I.
[5] In the following generation, Bartholomew Gilbert named Cape Cod during his 1602 expedition to establish a colony in New England.
[7] However Jonathan's younger son, Captain Thomas Gilbert, was said to have been “a brave and successful officer, and a leading man in the primitive navy of the colony”.