Holmes Family in America - History and Genealogy - Plymouth Colony 1692 to 2009. Family legend is that three Holmes brothers left England and came to the New World during the time the colonies were young. One settled on Manhattan Island, one in the Massachusetts Bay Colony, and the third in the Connecticut Colony. Nathaniel Holmes was born August 30, 1692 in Plimouth, Plimouth County, Massachusetts. Yes, with an "I" not a "y". Olive Lacy Holmes, the authors mother, was a descendant of Nathaniel. Many historical family photographs, documents, and references. It may also provide excellent starting points to begin further research.