Woodblock print of William Holmes’ party passing the Dutch fort in what is now Hartford.

Last fall, archaeological finds on the grounds of the Webb-Deane-Stevens Museum in Wethersfield reignited the burning question of whether Windsor or Wethersfield is older—a heartfelt but largely friendly town rivalry that has existed for centuries. Local and national press picked up on the story so we thought we’d share with you why we maintain that Windsor is Connecticut’s first English settlement, and the sources we draw upon to back up our claim. Some history:

In 1631, a delegation of sachems from the lower Connecticut Valley region traveled to the English colonies in the Massachusetts Bay area. They sought protection from the Mohawks (located west of the Hudson Valley) and the Pequots (located along Long Island Sound) in exchange for land. 1 The English were not interested in this offer until the Dutch established a trading post called House of Good Hope in the South Meadows area of what became Hartford sometime in the summer of 1633.

In September of 1633, a party of men from Plymouth, Massachusetts led by William Holmes sailed north up the Connecticut River and past the Dutch fort with the framing pieces for a house on board. Edmund B. O’Callahan notes a date of September 16th in the 1855 edition of his History of New Netherland, Volume I; Henry Stiles says it was September 26th in the 1891 edition of his History of Ancient Windsor, Volume I, and Massachusetts Bay Governor John Winthrop recorded the group’s arrival in Connecticut in his journal when he received the news on October 2, 1633.

This aerial view, looking south, shows the general location of the original Plymouth trading post at the confluence of the Connecticut and Farmington Rivers. The channel at the bottom of the photo was created much later. WHS collections 2003.41.62, photo by Philip F. Ellsworth Jr.

The Dutch were not pleased, threatening to fire their cannon on the Plymouth traders. Not dissuaded, the Plymouth folks continued north to establish their own trading post and settle near where the Farmington River joins the Connecticut. This new Plymouth trading post held an important geographical advantage over the Dutch one: it was now the first European trading post encountered by Native Americans traveling downriver with furs and other trade goods.

The Dutch traders at the House of Good Hope reported the English incursion to Dutch authorities in New Netherlands. House of Good Hope commissioner Jacob Van Carler was ordered to lodge formal protest against William Holmes, demanding his departure and a written reply. Neither occurred. Shortly afterward, the Dutch sent a force of 70 men to dislodge Holmes’s men but proved unsuccessful. The Dutch then sent forces north of the Plymouth fort to work with Native peoples to establish a new beachhead for trade, and to box in the Plymouth traders. This effort also failed because of a devastating outbreak of smallpox that decimated the original inhabitants.2

From period accounts such as Winthrop’s Journal, William Bradford’s Of Plimoth Plantation, and the letters of Plymouth company agent Jonathan Brewster, we know that the Plymouth traders repelled the Dutch attack, farmed, assisted Native Americans suffering from epidemics, offered sustenance, canoes, and guides to Massachusetts men who eventually settled in all three river towns, and occupied this trading post continuously for four years before being bought out by settlers from Dorchester, Massachusetts in May of 1637.

Wethersfield celebrates 1634 as its settlement year, based on when a group of “adventurers” (a seventeenth-century term for speculators or traders), under the leadership of John Oldham, arrived there. Although Massachusetts Governor John Winthrop’s Journal notes that Oldham and a group of three others went overland to the Connecticut Valley to trade in September of 1633, they did not stay, and Wethersfield does not acknowledge this year as its founding date.

On May 6, 1635, the Massachusetts Court granted the inhabitants of Watertown permission to remove themselves to settle elsewhere. These folks would eventually settle Wethersfield. On June 3, 1635, the Massachusetts Court granted the same liberties to inhabitants of Dorchester, who would eventually settle Windsor.

In early autumn of 1635, under the auspices of Roger Ludlow, a mostly Dorchester-based group of men, women, and children with livestock, began arriving in Windsor (or Matianuck as it was then known), straining to get ahead of yet another group sponsored by Sir Richard Saltonstall.3  October 15th, 1635, Governor John Winthrop noted that the Dorchester group had arrived safely.

Winter set in early that year. Many returned to Massachusetts Bay for the winter, but some stayed to look after the cattle. In the spring of 1636, several waves of settlers from Massachusetts Bay returned to populate what became the three river towns of Windsor, Hartford, and Wethersfield that joined together to form a colony.

While settlers of what would become Wethersfield received their permission to create a new town before settlers of what would become Windsor did, this was permission to establish a town, not settlement of a town. Stiles’ History of Ancient Windsor4 and History of Ancient Wethersfield5  both acknowledge that the families arriving in the fall of 1635 came from Dorchester, settling lands which became Windsor.

Connecticut histories by Benjamin Trumbull (1797), J. Hammond Trumbull (1886), and Albert Van Deusen (1961) cite a fall of 1633 founding date for Windsor. The exterior of Connecticut’s State Capitol building includes a marble vignette depicting Holmes’s settlement of Windsor with nothing analogous for Wethersfield. We in Windsor base our claim as first English settlement on the fact that Windsor has been continuously occupied by English-speaking people since September of 1633.

The First English Settlement monument is located at the southern end of the Loomis Chaffee School campus. WHS collections 2014.1.16a

Were Holmes’s group traders, not settlers? Were Oldham’s group settlers, not traders? Is a town a town before it is actually settled? What we do know is that in September of 1633, a group from Plymouth, Massachusetts led by William Holmes sailed up the Connecticut River past the Dutch Fort in Hartford, establishing a trading post in Windsor. From that date forward, English people have occupied this site, which has grown into the vibrant community we know as the Town of Windsor today.

By Christine Ermenc, executive director, 2019

Another useful source:
Edmund B. O’Callahan. History of New Netherland, or, New York Under the Dutch, Volume 1, New York: D. Appleton, 1855 p. 153.

oldest town in Connecticut

  1. John W. De Forest, History of the Indians of Connecticut, Hartford: Wm. Jas. Hamersley, 1851, pp. 65, 73-75.
  2. Henry R. Stiles, History of Ancient Windsor, Volume 1, Hartford: Case, Lockwood & Brainard,1891, pp. 25-26.
  3. Frank Thistlethwaite, Dorset Pilgrims, Interlaken, New York: Heart of the Lakes Publishing, 1993, pp. 102-106.
  4. Stiles History of Ancient Windsor, Volume I, p.52, note 1.
  5. Henry R. Stiles, History of Ancient Wethersfield, Volume I, New York: Grafton Press, 1904, p. 21.