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Indigenous era
The coastal areas and riverways of the the Connecticut River Valley was in turmoil were originally settled by various American Indian cultures, including the various who had been in the region for thousands of years. They relied on the rivers for fishing, water, and transportation.

The Algonquian tribes were dominant in the region. They were composed of various tribes, including the Pequot, the Mohegan, and the Podunk people. Anthropologists and historians contend that they split into the two competing groups sometime before contact with Europeans.

In the early 17th Century, the Connecticut River Valley was in turmoil. The Pequot aggressively extended their area of control at the expense of the the Connecticut River Valley Algonquian tribes and the Mohegan to the west, and the Lenape Algonquian people of Long Island to the south. The tribes contended for political dominance and control of the European fur trade. A series of epidemics over the course of the previous three decades had severely reduced the Indian populations, and there was a power vacuum in the area as a result. Importantly, the Pequot conquered the Podunk, the natives of the Windsor-area, and forced them to pay tribute.

First Contact and European Settlement
The Dutch were the first Europeans to explore the area. In 1614 the crew of the Onrust (Restless) whilst under the command of Captain Adriaen Block sailed from the recently-settled New Amsterdam up the Quinnehtukqut River.

They explored as far as present-day Hartford, just south of present-day Windsor. There they encountered a Podunk village.

The Pequot sold the land of present-day Windsor to the Dutch. The Podunk soon conceived the idea of inviting the English to settle in Connecticut. The earliest written record regarding this tribe is in 1631 when a sachem, called Wahginacut, journeyed to Massachusetts and Plymough Colonies to try to convince their governors to encourage the English to emigrate to the Connecticut Valley. In 1632, "the year before the Dutch began in the River", sachem Natawanute, (a.k.a. Attawanyut) presented Governor Winslow of Plymouth, MA with a tract of land in South Windsor.

By 1633, the Dutch had returned to the area the to erect a fortified trading house on the south bank of the Little River (now Park River), a tributary river of the Connecticut River. The Dutch West India Company had planned this fort, later known as the Fort Good Hope, to be the northeastern fortification and a trading center for the New Netherlands. The land on which the fort was constructed was part of a larger tract purchased on 8 June 1633 by Jacob van Curler on behalf of the Dutch West India Company from the Pequots. Curler soon added a block house and palisade to the post while New Amsterdam sent a small garrison and a pair of cannons. Some of the Podunk leaders invited a small party of settlers from Plymouth, Massachusetts, to settle upriver from the Dutch fort so as to act as a mediating force between the tribes. In exchange, they granted them a plot of land at the confluence of the Farmington River and the west side of the Connecticut River. It was about 50 mi up river from Long Island Sound, at the end of waters navigable by ship and above the Dutch fort at Hartford, offering an advantageous location for the English to trade with the native peoples before they reached the Dutch. (The Sicaog tribe had made a similar offer to mediate to the Dutch in New Amsterdam but the Dutch had far fewer settlers than the English, and they were not in a position to take up the opportunity.)

After Edward Winslow came from Plymouth to inspect the land, William Holmes led a small party, arriving at the site on September 26, 1633, where they founded a trading post. The spot of the trading post is at the confluence of the Farmington and Connecticut Rivers. The Loomis Chaffee School currently owns the land as the spot is now the school's sports fields.

Native Americans referred to the area as Matianuck.

In 1635, a party of around 30 people, sponsored by Sir Richard Saltonstall, and led by the Stiles brothers, Francis, John and Henry, settled in the Windsor area. Governor John Winthrop of the Massachusetts Bay Company acknowledged in a letter to Saltonstall that the Stiles party was the second group to settle Connecticut.

The first group of 60 or more people were led by Roger Ludlow, primary framer of the Fundamental Orders of Connecticut, having trekked overland from Dorchester, Massachusetts. They had arrived in the New World five years earlier on the ship Mary and John from Plymouth, England, and settled in Dorchester. Reverend Warham promptly renamed the Connecticut settlement "Dorchester". During the next few years, more settlers arrived from Dorchester, outnumbering and soon displacing the original Plymouth contingent, who returned to Plymouth in 1638 after selling their parcel to a Matthew Allyn of Hartford.

On February 21, 1637, the colony's General Court changed the name of the settlement from Dorchester to Windsor, named after the town of Windsor, Berkshire, on the River Thames in England. The same day, Windsor was incorporated as a town along with Hartford and Wethersfield.