Cupids is the oldest English settlement in what is now Canada. It was established by the London and Bristol Company of Merchant Venturers in August 1610 and the new colony's first governer was a Bristol merchant named John Guy. By the spring of 1613 the colony's population had grown to sixty-two people, at least sixteen structures had been built, including a fort, a saw mill, a grist mill and a brew house, much of the land has been cleared, crops were planted and livestock pastured. The first English child born in Canada was born at Cupids on March 27, 1613. He was the the son of Nicholas Guy.

From Cupids settlement spread to other parts of Conception Bay. Around 1618 some of the Cupids colonists left and established the Bristol's Hope plantation at Harbour Grace. Nicholas Guy himself move from Cupids to Carbonear were he was settled by 1631. The Guy's went on to become one of the chief planter families in Carbonear.

Some scholars once believed that the original colony was abandoned sometime in the 1620s. However, archaeological excavations and research conducted at Cupids since 1995 indicates the colony was occupied throughout most of the seventeenth century.