The Pequot and Mohawk tribes were at war in the area, and the Podunks were in the crossfire. The Pequots claimed their land and were forcing them to pay tribute.

The Podunk Indians invited a small party of settlers to come to the area of Windsor, and granted them a plot of land, where they would open a trading post. Their intent was that the settlers would provide a mediating force.

Another tribe, the Sicaogs, made a similar offer to the Dutch in New Amsterdam, but they declined to send settlers, since their interest in Connecticut was limited to the fur trade.

The Indians called the place Matianuck.

Edward Winslow from Plymouth inspected the site. William Holmes then led the first small group to Windsor on September 26, 1633. They settled at the confluence of the Farmington and on the west side of the Connecticut Rivers. They were about 50 miles up river, above the Dutch fort at Hartford, and were in a good position to trade with the Indians before the Dutch could do so.

Two years later, the Reverend John Warham arrived with 60 members of his congregation (a church organized in England in 1630). Rev. Warham called the settlement Dorchester, but the name was changed to Windsor in 1637 by the colony's General Court.

More settlers arrived in 1635 led by the Revs. Maverick and Warham with about 60 people who trekked overland from Dorchester, Massachusetts.


It took the settlers 3 weeks to go 92 miles. Their route took them as follows:

Dorchester, Mass.
Roxbury, Mass.
Muddy River (Brookline, Mass.)
Newtowne (Newton, Mass.)
Natik (Lake Cochituate, now in Framingham, Mass.)
Whitehall Lake (in Hopkington, Mass.)
Hassanamesit (now Farnumsville, Mass.)
Whitnsville Lake
Manchaug Lake (Sutton, Mass.)
Quinnebaug River (forded)
Lake Chaubunagungamaug (in Webster, Mass.)
Wabaguasset Lake (South Woodstock)
Crystal Lake
Pine Hill, Mount Hope Valley
Willimantic River (forded)
Shenipsit Lake
Connecticut River
Windsor, Connecticut (first called Dorchester).

More settlers from Dorchester moved to Windsor in the next few years. Outnumbering the original settlers they soon displaced the original Plymouth settlers, who mostly returned to Plymouth.

The first “highway” in Connecticut opened in 1638 between Windsor and Hartford. As other towns were settled further up the the Connecticut river like Springfield and Northampton, Massachusetts, trading routes were extended to all of them.

Old Descriptions of Windsor

The original boundaries of Windsor were very extensive, being about 46 miles in circumference, lying on both sides of the Connecticut River. Within the limits of the “town” there were ten distinct tribes or sovereignties. About the year 1670 it was estimated that there were in the town 19 Indians to one Englishman. The white men had a large fort a little N of the plat on which the first meeting house was erected.

The Palisado Green is the veritable shrine of Windsor history and romance. Very pleasant it is, as we see it now, in the warm sunset light of a summer's eve, lined with noble trees, behind whose waving tracery neat and elegant dwellings assert the presence of happy homes.

On this spot, more than two centuries ago our fathers dwelt. Here protected by the rude log defence which their own hands had thrown up, they slept secure from savage foe. Here stood the meeting house, wherein the gentle Warham and the earnest Huit preached and prayed. Here, too, was the little village graveyard, close under the palisado wall where – one by one – they put off life’s toils and cares, and laid them down to an eternal rest.

The history of this interesting locality is as follows:

Upon the breaking out of the Pequot War in 1637, the Windsor people surrounded their dwellings at this spot with a fortification or palisado. This consisted of strong high stakes or posts, set close together, and suitably strengthened on the inside, while on the outside a wide ditch was dug, the dirt from which was thrown against the palisades, and the whole formed a tolerably strong defence against any slender resources which the uncivilized Indians could bring to bear against it.

It was of course necessary to keep a constant guard within the enclosure, to prevent the enemy from climbing over, or setting fire to the palisades. It was the fatigue of supplying these watches that so exhausted the men (as Mr. Ludlow sorrowfully wrote to Mr. Pyncheon, at Springfield, Mass., during the absence of the Windsor men on the Pequot expedition) “that they could scarce stand upon their legs.”

The whole length of this line of palisades was more than three-fourths of a mile, enclosing an irregular parallelogram of considerable extent. From the southwest corner of the burying ground it extended along the brow of the hill overlooking the Farmington river, eastward to the Meadow hill. This south line was 990 feet long. Its west line extended northward 1,139 feet, along the brow of the hill west of the burying ground. Its east line ran along the brow of the Meadow Hill, 1,320 feet northward; and its north line ran across from hill to hill, near the present residence of Mrs. Giles Ellsworth, and was 325 feet in length.

When the first palisado was built, those who had their home-lots within its limits resigned their title for the benefit of the whole community. Matthew Grant, for instance, says that he originally had six acres, but resigned it all up, except where his buildings stood. This was the case with others. The following plan of the palisado was drawn in 1654 by Matthew Grant, who was at the time Recorder:

One writer at Windsor thus speaks:

And seeing I am entered into the palisado, I will speak a little of the original of it; about 1637 years, when the English had war with the Pequot Indians, our inhabitants on Sandy Bank gathered themselves nearer together from their remote dwellings, to provide for their safety, set upon fortifying, and with palizado which (land) some particular men resigned up out of their properties for that end, and (it) was laid out into small parcels, to build upon; some four rods in breadth, some five, six, seven, some eight – it was set out after this manner.

These building places were at first laid out of one length, that was sixteen rods, but differ (in breadth) as aforesd. Also on all sides within the outmost fence, there was left two rods in breadth for a common way, to go round within side the Palisado, to the rear of the building lots. This left an open space in the centre (marked W in the plan) nearly 20 rods wide and 30 rods long.

When peace was again restored, “divers men left their places (in the Palisado) and returned to their lots (outside) for their conveniences. Some that staid (by consent of the town) enlarged their gardens. Some had 2, some 3, some 4 plats to their propriety, with the use of the two rods in breadth round the outside, everyone according to his breadth, only with this reserve concerning the two rods, that if in future time there be need of former fortification to be repaired, that then each man should resign up the two aforesd two rods for a common Burying Ground, one particular parcel that is six rods in breadth, all the length of one side, and one end; take it together, it is eight rod in breadth, and eighteen in length.” – From History of Ancient Windsor.

Our Windsor Ancestors

Thomas Dewey

Thomas Orton

Isaac Sheldon

John Williams


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