The first thing to note is that Barbados in the mid-to-late 17th century was the wealthiest, most populous, and most economically productive colony in the Anglo-American world. It was one of the most important destinations for English migrants; about 2/3 of the migrants who came to the English colonies between 1640 and 1660 went to the West Indies, and the lion's share wound up in Barbados. The tiny island attracted far more migrants in the 17th century than all of New England: the numbers are hard to pin down, but no more than 30,000 migrants came to New England during the so-called Great Migration, while perhaps as many as 100,000 people from the British Isles made their way to Barbados.

Most of these migrants came as indentured servants - i.e., typically impoverished young men in search of employment, who signed on to a term of service for several years in exchange for the cost of passage to the New World. In the early years of the colony, they mostly worked as labourers on tobacco plantations, but during the course of the 17th century the island's economy became increasingly based on sugar production. With the emphasis on sugar came an increasing reliance on slaves imported from Africa, and by the end of the 17th century English migrants were more likely to choose the Chesapeake or the Middle Colonies as their destination.

Although New England and Barbados were very different worlds, there was some connection between the two - the second of son of John Winthrop, the first governor of Massachusetts, Henry, tried his hand at tobacco planting in Barbados before he finally settled in Connecticut. By the end of the 17th century, shipbuilding and the carrying trade were becoming increasingly important to the economy of New England (including to Maine ports such as Falmouth, Kittery, Wells, and York). One of the major ports of call for New England merchants was Barbados - vessels would sail to the West Indies carrying salted cod and other commodities, which would be sold at Bridgetown to planters in need of protein for their slaves and servants. The merchant vessels would then load molasses and sugar into their cargo holds, which they would transport to England and sell for trade credits and manufactured goods. (This system is commonly known as the "triangular trade", although it was in fact more complicated than my sketch here.)

It wouldn't be surprising, under these circumstances, that a migrant from England would wind up in Barbados in the late 1600s, nor that his son - at a time when the island was facing growing population pressures and an increasing reliance on an enslaved labour force - would board a merchant vessel and seek greener pastures in northern New England.

For a recent overview of the early history of Barbados - which emphasizes the ways in which migrants to the colony tried to re-create English customs and institutions in a tropical setting - see Larry Gragg's Englishmen Transplanted: The English Colonization of Barbados, 1627-1660.