A year later a more respectable entrepreneur came to the island. John Winter was the agent for merchant Robert Trelawney of Plymouth, in England’s west country, and soon developed a brisk and profitable trade in fish and furs. There were some hardships in life on the frontier: in July 1637, Winter, who then employed about sixty men, wrote Trelawney somewhat plaintively that his wife needed a "firkin of gray sope," as well as "six brazen panns," "since our earthen pannes weare half broken & heare I cann gett none....’In 1636 he inaugurated Casco Bay shipbuilding with the construction of the Richmond, of thirty tons or so, and traded as far south as New York. Meanwhile, he was shipping fish, furs, and "sassafras enough to cure all the gout in England" back to Plymouth. True enough, the Richmond was not the first Maine-built vessel. In 1607 the short-lived Popham Colony at the mouth of the Kennebec launched the Virginia, about the same size as the Richmond, and after the failure of Popham sailed between England and Virginia for about twenty years until, returning home with a cargo of tobacco, she piled up on the coast of Ireland.
The neck of land on which the present city of Portland was originally settled juts eastward into Casco Bay some nine miles north of Richmond Island, on the north shore of the estuary of the Fore River. In 1632 Richard Tucker and George Cleeves sought to settle at the mouth of the Spurwink River, opposite Richmond Island, but Winter refused permission, and the pair headed for the neck the Abnaki called "Machigonne," or Great Knee, and settled near the shore at the bottom of the rise of land now called Munjoy Hill. They went into competition with Winter. In 1637 Sir Ferdinando Gorges, the Proprietor of Maine, granted them title to their land on what by then was called Casco Neck. In 1658 officials in Massachusetts, which at that time included the Province of Maine, set the boundaries of the new town of Falmouth, as it was to be called, as encompassing present Portland, South Portland, Cape Elizabeth, Falmouth and Westbrook. By 1675 the growing settlement had forty families, spread over a fairly wide stretch of newly cleared former wilderness.
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