Jonah and Hannah Westover settled in Connecticut and raised a family of community servants as the Colony expanded. Military service was compulsory. So their sons were late in marrying and establishing their own families. Jonas Westover Jr. married Abigail Case, taking charge of the Westover Plantation in Simsbury, Connecticut and worked that land until tragedy struck in 1714. Younger brother Jonathan, still a unmarried at 40, took charge of the surviving Westover children and moved them North and West into Sheffield, Massachusetts.

There the children, nieces and nephews of Jonathan Westover thrived and expanded in the next generation. These families, led by community leaders such as John Westover, clerk of the Church of England in Sheffield, would power Colonies such as Massachusetts during the American Revolution.