Template:Wp-Windsor, Connecticut-History

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The coastal areas and riverways were traditional areas of settlement by various American Indian cultures, who had been in the region for thousands of years. They relied on the rivers for fishing, water and transportation. Before European contact, the historic Pequot and Mohegan tribes had been one Algonquian-speaking people. After they separated, they became competitors and traditional enemies in the Connecticut region.

During the first part of the 17th century, the Pequot and Mohegan nations had been at war. The Podunk were forced to pay tribute to the more powerful Pequot, who claimed their land. Eventually, the Podunk invited a small party of settlers from Plymouth, Massachusetts, to settle as a mediating force between the other 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. 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. It was about 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 Indians before they reached the Dutch. (The Sicaog tribe had made a similar offer to mediate to the Dutch in New Amsterdam. New Netherland had far fewer European settlers than New England, and they were not in a position to take up the opportunity.)

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.

Several "daughter towns" were formed from Windsor's original boundaries. These include portions or all of Barkhamsted, Bloomfield, Bolton, Colebrook, Coventry, East Granby, East Windsor, Ellington, Enfield, Granby, Harwinton, Litchfield, Manchester, Morris, Simsbury, South Windsor, Suffield, Tolland, Torrington, Vernon, and Windsor Locks.

The first "highway" in the Connecticut Colony opened in 1638 between Windsor and Hartford. Two years later, the highway was extended north to the colony's 1636 settlement at Springfield, with the road also connecting to Wethersfield and thus the four settlements that came to dominate the region for much of colonial history were connected.

In the summer of 1640, an event took place that would forever change the boundaries of the Connecticut River Valley. During a grain famine, the founder of Springfield, William Pynchon, was given authority by Windsor and Hartford to negotiate a price for grain for the three settlements with the natives. First, the natives refused to sell grain at the usual market price, and then refused to sell it at "a reasonable price". Pynchon refused to buy it, attempting to teach the natives a peaceful lesson about integrity and reliability. Windsor's cattle were starving, however, and the citizens of Hartford were furious. With Windsor's consent, Hartford commissioned the famous Indian fighter John Mason to travel to Springfield with "money in one hand and a sword in the other" to threaten the natives, and thereby force the grain trade. The natives capitulated and ultimately sold their grain. After "negotiating the trade", Mason refused to share the grain with Springfield, and, to add further insult, insisted that Springfield pay a tax when sailing ships passed Windsor. Outraged, Springfield forever sided with the Massachusetts Bay Colony, a faraway theocracy based in Boston, rather than with the Connecticut Colony, which was much closer geographically and far more compatible ideologically. Windsor played a neutral role in the colonial rivalry between Hartford and Springfield; however, Windsor's direct border with both settlements caused many discussions about whether to align with Massachusetts or Connecticut. Ultimately, Windsor sided with Connecticut.^[1]

The Hartford & Springfield Street Railway, a trolley, connected with the Connecticut Company in Windsor Center until 1925. Buses replaced trolleys between Rainbow (a northern section of Windsor) and Windsor Center in 1930. Trolley cars continued to run from Windsor to Hartford until 1940.

The original Windsor settlers have many descendants around the country and beyond. Many are members of the Descendants of the Founders of Ancient Windsor (DFAW).

When the Springfield Line of the NY, New Haven & Hartford RR was built, station stops included Windsor station in Windsor Center with stations also at Wilson in the south of town and Hayden in the north, named for owners who provided land for the railroad right of way. The line was double tracked until the late 1990s and redouble tracked in 2018. Sidings at Windsor station allowed cars to be spotted at the freight house and on the Loomis trestle just to its south. The trestle was removed in the late 1980s. An 1856 brownstone arch bridge carries the tracks over Pleasant St and the Farmington River. Incorporating a horizontal curve, its engineering was noteworthy when built. Following a fatal grade crossing accident, a three-track-wide plate girder bridge was installed to carry tracks over Palisado Avenue.