A party of Plymouth settlers under the leadership of William Holmes sailed upriver past the Dutch fort in Hartford, arriving on September 26, 1633 to establish a trading post just south of where the Farmington River joins the Connecticut. (Stiles, p. 25) Within the next two years, two other groups of settlers would arrive, the first from Dorchester Massachusetts and the second, a group that had just migrated from England under the auspices of Lord Saltonstall.

By 1635, English groups had established plantations or towns at Dorchester (renamed Windsor), Newtowne (renamed Hartford) and Watertowne (renamed Wethersfield).  In April of 1636, representatives from the three towns held a court in Hartford, an alliance that would evolve into the Colony of Connecticut.  One year later, that same court authorized an “offensive warr” against the Pequot under the command of Captain John Mason of Windsor.  In Windsor, a palisade was hastily erected for protection.  Settlers within the palisaded area temporarily gave up their home lots to accommodate families moving in from outside the Palisado.  The quick and brutal engagement between the River Town and Pequot forces under the command of Windsor’s Captain John Mason resulted in decimation of the Pequot peoples.  Windsor’s palisade was gone by 1640 although reference to it remains to this day in Windsor’s Palisado Green.

The early town of Windsor was distinguished from neighboring towns by its size. The first land distribution in Windsor was 16,000 acres distributed to 92 settling families.