William Holmes, passing a Dutch Fort, (mistakenly labeled as John Holmes), Hartford State Capital. Sculpture by Paul Bartlett. Photo by Bill Hosley.

In beginning a series of short introductions to Windsor’s founders, it is appropriate to start with Lieutenant William Holmes. His leadership established the first trading post here and paved the way for all future English settlers.

Holmes is believed to have arrived in Plymouth Colony in 1632, at about 22 years old. A soldier and Freeman, he was respected enough that by 1633, he was trusted to captain the party of traders aboard the colony’s “great new barke,” and set up the trading post at what is now Windsor (William Bradford, Bradford’s History of Plimoth Plantation, Boston: Wright & Potter, 1899, p 372). Holmes knew his venture would be opposed by both the Dutch and the Pequots. Windsor was entangled in a land dispute that had been underway for years. The English claimed the land because it had been granted to them by their King. The Dutch claimed it because they had purchased it from the Pequots and had already built a fort at present-day Hartford, and the River Indians claimed it because it had been theirs before the Pequots expelled them from the region. To strengthen their claim to the land, Holmes’s traders carried Natawante, a sachem of the River Indians, aboard their barque in hopes of restoring him to his native territory and exploiting their alliance with him.

Detail of the sculpture showing the Holmes party.

Tensions mounted as Holmes’s party approached the Dutch fort when “the Dutch demanded what they intended, and whither they would goe.” Holmes’s men answered, “up the river to trade.” At this point, the Dutch ordered the English barque to stop, “or els they would shoote them” with the two cannons they had recently installed. Holmes’s traders responded, “they had commission from the Gov[erno]r of Plimoth to goe up the river to such a place,” and must obey their orders whether the Dutch fired upon them or not (Bradford, 373). The Dutch continued to threaten Holmes’s vessel, but did not shoot. Holmes’s men successfully landed at Windsor, erected the small house frame they had brought in the hold of their ship, and built a palisade around it. The Dutch and their allies sent a war party to Windsor afterward, but seeing the fortified house and fearing bloodshed, made peace instead. The new trading post remained. The area became a favorable place for other English families to settle.

Holmes himself did not remain in Windsor long, but returned to Plymouth. By 1635/6, he appears again in the Plymouth tax lists. Along with Myles Standish, he was appointed to conduct military training for the men of Plymouth and Duxbury. Holmes was given charge of the town guard, and was elected leader of a company of Plymouth men in the Pequot War. Though he resided elsewhere, Holmes retained some control over the Windsor trading post until 1638, when he sold Plymouth’s lands there to Matthew Allyn.

Holmes moved to Duxbury in 1639, returned to England to fight in the English Civil War, and came back to the Colonies shortly thereafter. He never married, never had any children, and died in Boston in November 1649. He left his entire estate to female relatives then living in Antigua and London, as well as 20 pounds to his “loving & kind kinsman Job Hawkyns.” Hawkins’s relationship to Holmes is unknown, but he paid Holmes’s considerable bar tabs for him, and was eventually granted the use of Holmes’s lands in order to settle his debts.

William Holmes lived a life of bravery and was no stranger to adventure. He was a trusted leader and skilled negotiator capable of managing the complex, multi-cultural interactions inherent to life on the American frontier. His legacy is Windsor, a settlement made possible through his leadership in fortifying the outpost with palisades and maintaining alliances with native peoples.


by Kristen Wetzel Wands, Curator