The Working Waterfront

A circuitous Mayflower connection

Love and shipmates, a generational story

By Phil Crossman
Posted 2023-12-28
Last Modified 2023-12-28

This is a remarkably coincidental and clearly destined love story resulting from the very diverse and circuitous travels of nine descendant generations of two Mayflower passengers, emerging, finally, 300 years later, in parallel.

The Mayflower arrived in what is now Provincetown Harbor, Cape Cod on Nov. 11, 1620. On board were 102 individuals, two-thirds of them men.

Among those men were William Brewster and his wife Mary, and Richard Warren who arrived alone, having left his wife Elizabeth in England with a promise she’d join him once established..

William and Mary Brewster and Richard Warren each survived that first particularly awful first winter…

William Brewster was born in 1567 in Scrooby Manor, England and it was there in Scrooby that the Pilgrims had their beginning. At the time it was treasonous to form a religious assembly outside the Church of England. Nonetheless, in 1606, a group that included William Brewster created a simple church congregation around a covenant that simply gave equal rights to every individual and accepted no authority, ecclesiastical or civil, except that which the congregation adopted by mutual consent. The king was not happy, to such an extent that whatever hostility they might encounter in the New World seemed worth it.

Richard Warren was born in England in 1578. He was not among the Pilgrim congregation. Rather, he was looking for adventure and new opportunities.

After many delays, real and pretended, the Speedwell and its companion ship Mayflower finally set sail for America, but the Speedwell suffered one after another suspect leakages or malfunctions, returning each time for repairs and accompanied each time by the Mayflower and its ever more exasperated passengers.

Finally, after it became clear the Speedwell command had, in fact, no interest in fulfilling its mission, some of its passengers joined others on the Mayflower and on Sept. 6, 1620, the overloaded ship finally found herself underway for America.

The ship was 150 feet long: an allotment, therefore, of one foot, four and a half inches abeam for each of the 102 individuals and crew on board, for their provisions, nourishment, livestock, furniture, and clothing.

The Mayflower sailed to harbor at what is now Cape Cod on Nov. 11, 1620, and the appeal of simply settling there instead of moving on to Virginia as planned was made even more inviting by a shortage of supplies and by the reality of 102 souls having been at sea and too close for comfort for over two months.

William and Mary Brewster and Richard Warren each survived that first particularly awful first winter during which over half—52—of those who’d made the journey died, a few men but most of them women and children.

Ultimately, nine generations of William and Mary’s descendants traveled all around North America and Canada for the next 300 years, until one sunny summer day in 1921 when a handsome 17-year-old, then a new steam engineer on the Governor Baldwell, a steamer serving the coast, stepped off the boat when it docked in Vinalhaven.

During an hour-long stopover, he got some lunch and wandered through town. At the end of the little but vibrant downtown area, a sidewalk across the street led past a block of apartments uphill toward a stunning old mansion.

On that day, a lovely and flirtatious girl was sunning herself on the stone wall surrounding the grand old Moses Webster House. She was the ninth great granddaughter of Richard and Elizabeth Warren and coming up the sidewalk toward her, gnawing on a sandwich he’d picked up in town, came the increasingly intrigued ninth great grandson of William and Mary Brewster. As he got closer, she arranged herself provocatively.

It was love at first sight for him and it was reciprocated by her, and not long after, the two were married. Phyllis was 16.

Phil Crossman lives on Vinalhaven where he owns the Tidewater Motel. He may be contacted at