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The Founding of Windsor

Updated: Jun 3, 2021

Moving south from Boston along the northeastern coast of North America there are three significant river valleys where the early European colonists settled: the Connecticut, the Housatonic, and the Hudson. The rivers that formed these valleys run from north to south into the Atlantic. As the crow flies, the Connecticut River is only about 80 miles east of Boston, but by boat along the coast it’s more like 250 miles.

The Connecticut River is the longest river in New England. It flows 410 miles southward along the Vermont-New Hampshire border through western Massachusetts and the center of Connecticut before emptying into Long Island Sound near the town of Old Saybrook. The name was derived from an Indian word meaning "long tidal river". In the early days it was referred to as the Great River, or just the River. Not only was this river an important fur trade route, but the meadows along its banks were very fertile.

Humans have lived along the river for 13,000 years, since the last glaciers receded. The earliest people hunted and fished on the shores of a large lake that filled the ConnecticutValley and when the lake drained some 8,000 years ago they moved into the silt-rich bottomlands. By the time the English settlers began to arrive these people had developed into a number of Native American nations, mostly speaking the Algonquin language. The most powerful tribe in the Valley were the Pocumtucks, who were paid tribute by weaker groups, but who themselves paid tribute to the Pequots in Connecticut and to the Mohicans along the Massachusetts-New York border. The Pocumtucks and other groups along the River were hard hit by the epidemics that surged among New England Natives in 1616-17 and particularly in 1634. Their numbers reduced, they contracted their area and abandoned many of their villages. The natives in the immediate area of Windsor were friendly and helpful to the European settlers when they came. But during the winter of 1633-34 all but a few of them died.

The first Europeans to explore the Connecticut River valley were the Dutch, when in 1614 the Dutch explorer Adriaen Block sailed up the river as far as the Hartford area. Later the area was explored by both the Pilgrims from the Plymouth Colony and the Puritans from the Massachusetts Bay Colony. In April of 1631, seeking a defensive buffer against the aggressive Pequot tribe, representatives of the River Indians went to Boston and then to Plymouth to ask these colonies to make settlements in the Connecticut River valley. They described it as a fertile and abundant land, and offered corn and 80 beaver skins a year to whomever settled there.

Governor Winslow of Plymouth was interested enough by the offer to go see this land for himself. He found it to be just as the Indians described, and so in 1633 he proposed to the Massachusetts Bay Colony a joint settlement of the valley. The offer was refused, perhaps because some of the Bay Colony people were already considering plans to settle there themselves and were not interested in sharing the land with people from Plymouth.[1]

In that year groups from all three of the northern European colonies, New Amsterdam, Plymouth and Massachusetts Bay, explored the valley. The Dutch claimed this land and were worried, with good reason as it turned out, that the English might attempt to settle there. So in the summer of 1633 Governor Van Twiller of New Amsterdam sent a party to erect a fort at the present site of Hartford. They mounted two cannon and named the fort the “House of Hope”.[2]

The Plymouth Colony sent a party of their own later in the summer of 1633 under the command of Lieutenant William Holmes. On September 26, 1633 they arrived by boat and set up a trading post at what is now Windsor, at the junction of the Connecticut and the Farmington Rivers, and immediately erected a building surrounded by a stockade fort or “palisado.”[3]

They purchased land just south of the junction of rivers from the Sicaog and Tunxis Indians. After building and fortifying the trading post, the ship and crew returned to Plymouth leaving Jonathan Brewster and a small group of men in charge. A month later Governor Van Twiller sent 70 men to evict them. Fortunately for the English, the Dutch found them too well entrenched to be easily dislodged. After a few hostile demonstrations, the Dutch returned to New Amsterdam and took no further action against the settlement at Windsor.[4]

About the same time in 1633 the Massachusetts Bay Colony also sent a party led by John Oldham to explore an overland route to the Connecticut River. They followed a well-established Indian trail known as the Great Trail (later called the Old Connecticut Path). Oldham’s report was positive and the Colony was encouraged to begin to settle the valley.

By this time many of the early settlers of the Massachusetts Bay Colony were ready to emigrate. Though committed Puritans whose purpose was to form a model Christian society in what they viewed as an unspoiled wilderness, some of them felt Governor Winthrop’s version of this society was too restrictive. He believed that God governed society through only a few select men while others believed all the governed should have a voice in the government. Besides, the seacoast was already becoming crowded, and the best land was taken. So this was an opportunity that ambitious young men like Thomas and his friends were going to take.

They heard talk of an advance party from Dorchester that would go to the Connecticut River sometime in the summer of 1635. But before they could join this group, Thomas and a couple of his friends needed to take care of an essential piece of business; they needed to be declared “Freemen” so that they would have a vote in the public and religious affairs of the settlement they were about to found. To qualify they had to be mature male church members who had undergone a “transforming religious experience by God’s grace” and they had to take the Freeman Oath.[5] An oath in those times was taken very seriously, as though made directly to God. But prior to the oath being shortened and modified in 1634, many refused to take it. The portion to which they objected was the promise to obey the Governor. That was changed to obedience to “the common weale.”

On May 6, 1635 at the General Court of the Massachusetts Bay Colony in Boston, Thomas, now 30 years old, took the Freeman Oath along with his friends Aaron Cook, Robert Dibble, George Phelps, Samuel Allen, and Thomas Hoskins. In this oath they acknowledged themselves to be subject to the government of the Colony and they dedicated themselves to its protection.

At this same meeting of the Court, a prominent Dorchester settler, Roger Ludlow, failed to succeed Thomas Dudley as governor. He had made too many enemies, and he realized it was time for him to seek a place elsewhere. Ludlow lost no time and promptly recruited twelve Dorchester men to explore the Connecticut River valley and find a proper location for a new settlement. Then an event occurred that gave their plan a sense of urgency. On June 16 the barque Christian arrived from England with twenty “servants” (people in the employ) of Sir Richard Saltonstall and their leader, Francis Stiles. They had been commissioned by Saltonstall to take up land on the Connecticut River.

This was a reminder that there were prior claims to this land and competing interests. It was crucial that the Dorchester expedition establish a de facto right to land in the Connecticut River valley by taking possession of a suitable site there before Stiles and his party should arrive. So, the Saltonstall group was purposefully held up for ten days in Boston with entertainment and delays in finding a sloop to sail them around the coast, all to give the Dorchester party time to arrive first at the Connecticut River.[6]

Thomas and the twelve other men from Dorchester hurriedly set out on the Great Trail. They had a hundred or so miles to go, and they traveled through what for them probably seemed a wilderness. But it was not. The Natives who had inhabited that land for many generations had a highly organized rural economy and they managed it intelligently. They enjoyed an abundance of natural resources: forests, rivers, meadows, wild produce, cultivated crops, game and fish. They had well-defined traditions and territorial limits. They had no domesticated livestock and their grain crop was limited to maize (the English insisted on calling it corn), which they cultivated with a variety of vegetables, such as beans and squashes. These crops were raised around tree stumps and in roughly cleared patches of ground rather than in open, cultivated fields in the European manner. When a field wore out, they’d simply moved their village to more fertile ground.[7]

They harvested wild berries and plants, and hunted game. Forest management was essential to their economy. The hardwoods, oaks, chestnut and hickory, and hemlock and pine were important resources for them, and they periodically set fire to the underbrush to make it easier to hunt and to encourage new growth. Far from being a tangled, impenetrable wilderness, the forest was for the most part open, clear of underbrush, more like a wild native parkland. Though the Native villages would be moved from time to time, each tribe had its own territory and discouraged poaching from neighboring tribes.

The Great Trail (also called the Great Path) was a network of footpaths created by Algonquin and Iroquois-speaking peoples prior to the arrival of Europeans. It connected the Great Lakes region of Canada to New England and the mid-Atlantic. Many major highways in the northeastern United State follow the routes set down centuries ago by Native Americans moving along these trails.

At first the Dorchester group’s trek lay through the territory of the Massachusetts Indians, which then gave way to the territories of the Nipmucks, the Mohegans and the various “River Indians” of the Connecticut River valley. By way of the Trail that linked Indian villages, the group finally reached their destination on the west bank of the Great River toward the end of June, some sixty miles north of the river’s mouth in Long Island Sound. This was a place the Indians called Matianuck. This was where the Plymouth Colony had established its trading post, and here the Dorchester group stayed for ten days while being provisioned. They then left to look for a site for their settlement.

They found what they were looking for just above the trading post on the west side of what they called the Great River. It was a stretch of river meadow and a bluff which was a spot favored by the Natives of that region. It was fertile land and a great place for fishing for salmon and shad. It also had strategic importance; it was the only fording place for many miles and the principal trails of the Native Americans converged there. On the east bank was the fortified headquarters of the local Native tribe, the Podunks. Though this spot was claimed by both the Plymouth Colony and the Saltonstall contingent, this inconvenience was simply brushed aside and this was the spot the Dorchester group chose to settle.

All summer a trickle of pioneers who had heard of the venture arrived at the new settlement, and then at the end of October an organized group of sixty Dorchester people arrived after walking for fourteen days along the Great Trail. It was too late in the year to erect anything like permanent buildings, so for temporary shelters they dug into the sides of the river bluff to make homes enclosed on three sides by dirt, just as they had done that first difficult year of the founding of Dorchester. In the front of their shelters they inserted posts for a door and built roofs with wood and thatch. Unfortunately, winter came early that year and the river was frozen over by mid-November, preventing the arrival of ships with their possessions and provisions. The situation quickly became desperate.

Some of the settlers decided to return to Dorchester for the winter. They traveled down the river, freed a ship from the ice, and sailed back to the Bay Colony while Ludlow with the twelve men of the original company returned to Dorchester on the Great Trail. But some of the settlers were left behind to look after the cattle and to hold the land. They survived on acorns, malt, grain and food given them by the Natives and the few earlier settlers. But most of the cattle they had so laboriously driven there from the coast died of starvation. Strangely, though, those cattle that had arrived late and were left to fend for themselves on the east side of the river survived the winter very well.

Ludlow’s group had a difficult return. One man fell into a river, was trapped under the ice, and drowned. All of them might have starved to death had they not run across a Native wigwam with provisions inside. They gratefully helped themselves to the food they found. They arrived at the Bay on November 26, eleven days after setting off on their journey. Even though the situation they found at Dorchester was bleak, because of the hardships they had all endured there was little enthusiasm for continuing the venture. But by spring confidence had returned and plans were made for a full-scale emigration.

The Migration to the Great River In April 1636 most of the congregation of the Dorchester church was migrating to this new settlement on the Connecticut River.[8] Most of the people went overland, but bulky and heavy possessions went by sea. Ludlow and his group were back on the Connecticut River by the end of April, and even the Reverend Warham arrived by July, though he left his family behind until a decent home could be built. Thomas had sold his home lot in Dorchester and was excited about this new adventure and the prospect of working his own farm, getting married and raising a family.

The move was orderly, with families, bachelors and servants traveling in groups, carrying what they could by pack-horse and driving their cattle before them. They were well-provisioned and the spring weather was dry and free of bothersome mosquitoes, so the trip was not a great hardship. “The journey was made easier and more pleasant because it lay mostly along a chain of Indian villages at springs, ponds, lakes and fords which were staging camps of hospitality.”[9]

“The Dorchester caravan set out on a road already familiar to some of them by way of Roxbury and Muddy River, past New Town, then nine or so miles to the falls of the Charles River and then twenty more through the Natik country to the ancient lake and beaver dam at what is now South Framingham; thence, by way of Magunko Hill, ‘a place of great trees’, they came to Whitehall Lake, set in a forest of gigantic oaks where the pioneers ‘worshipped in Nature’s great cathedral’ (present-day Hopkinton). Another day would take them over the ford of the river where Nipmucks had their royal seat of Hassanamesit (modern Farnumsville), a ‘bating place of note for early travelers’. Westward the country became hilly and wilder. The trail brought them by way of two lakes, Whitinsville and Mancahug, to their welcome half-way mark. This was a sacred Indian reserve called Chaubunagungamaug, or ‘Great Pond’, a remote, peaceful and beautiful lake, bordered by a forest of Douglas fir where the Nipmucks kept their sacred rites (modern Webster). They looked on it as a sort of Elysian Fields, the abode of the Great Spirit and their departed ancestors. Then, after fording yet another river, the Quinnebaug, they struggled over to Wabaquasset Lake at whose waters the Indians were wont to congregate at the time of the spring planting (modern Woodstock).

These Indians were reputed to be especially friendly to the English because they had sent corn to the Bay to relieve them during that first starving winter of 1630. Thence by way of Crystal Lake and the Pochaug River, the travelers found themselves in the attractive oak and chestnut country of Mount Hope Valley at a place which they called Pine Hill because of its isolated pine landmark. Thereafter there remained only one sizeable river to be forded, that of the Willimantic, in country which again was a favorite Indian fishing and hunting ground. Finally, there were eighteen or so miles still to travel by way of Shenipsit Lake until that eagerly awaited moment when, after a journey of about three weeks and ninety-two miles, the Dorchester company emerged from green, dappled forest into bright sunlight, and, beyond, the expanse of the great river of the Connecticut. There, on its opposite bank, they could make out the broad stretch of meadowland which was to be their home.”[10]

New Dorchester By early June the Dorchester people at Maniatuck were numerous and confident enough in their future in this place to give it a name. They called it, once again, Dorchester. It must have been a primitive place, just an encampment that summer. At first they sheltered in the dugout shanties along the “Sandy Bank” bordering the river meadow. Many of their possessions and most of their heavy equipment were lost in a ship wrecked on its way from the Bay. But soon they began to construct their first wooden houses and to pace out their home lots just west of the “Great Meadow,” with an inner cluster of homes about a central village green. It must have been easier this time; after all, they’d done this before, under more difficult conditions, at the time they first landed in New England six years earlier. This time they knew what to expect, so they must have been in a hurry to complete their homes, plant corn, cut timber and prepare for winter.

By fall the new plantation was firmly established. According to an estimate made a hundred years later, this new Dorchester had a population of fifty or so families in 1636, about 235 people, together with another thirty or so bachelors, including Thomas. “The great majority came from Dorchester-on-the-Bay. Of 131 heads of families or individuals who had been granted land at Dorchester (deducting three who had died), fifty-four, with their families, undertook that journey to Matiatuck to become original settlers, that is, about 40 percent of the Dorchester they had left. These fifty-four Dorchester men were the hard core of the new settlement. Moreover, that core belonged disproportionately to the original company from the West Country. Of the fifty-four heads of families, forty, or 74 percent, had been born and bred in Dorset, Somerset or Devon; and of these about thirty-five, or 65 percent, had crossed the Atlantic on the Mary and John or one of John White’s associated ships. His recruits were proving a persistently cohesive group, no longer just a ship’s company but a pioneer community bound intimately together by a common folk memory and experience of hardships shared over two uprootings.”[13]

The settlers knew their position was exposed and threatened. There were not only competing English interests, but also the Dutch and the Indians to contend with. They had little more than squatters’ rights, and the Dutch still held their fort down river. The Stiles party had been forced to disembark upstream at Poquonnock, but Salstonstall still made a claim to the land, as did the Plymouth Colony. That doesn’t mean that there wasn’t also a good deal of cooperation among the English settlers. In this first year (1636) a Commission was established to govern the Connecticut plantations, for example, and at its June meeting a survey of the boundaries between the plantations was ordered and a watch was formed in each town. Every able-bodied man was to have in readiness a musket, two pounds of powder and twenty lead bullets. These were the first steps in creating a trainband [militia] for the new colony.

On the whole, the Natives had welcomed the arrival of the English, and the Puritans had been conscientious in their dealings with them. But this was beginning to change. The Native Americans had little resistance to European diseases and in the 1620s and 1630s they died in great numbers of chickenpox and then smallpox, resulting in the abandonment of many villages and hunting lands. (One reason why the English found Native land so easy to acquire.) In some areas the Natives had ceased to manage the land, which then reverted to scrub. There was a general decline in their rural economy and morale, and an upset in the political equilibrium among the tribes. The Natives, with good reason, began to blame the English for these problems.

War with the Pequots The first major difficulty came from a branch of the Mohegans, the aggressively migrating Pequots (Algonquin for “destroyer”), who by the time of the settlements on the Great (Connecticut) River had become well established along the coast from the Narragansetts to the Great River. The Pequots were expansionist and had a reputation for brutality. It was in hope of aid against the Pequots that the Connecticut River tribes had invited the English to settle there. But the arrival of the settlers provoked the hostility of the Pequots and the result was a series of bloody incidents.

The first victim was a Captain Stone, who was killed with his crew while exploring the Connecticut River in 1634. Then in July of 1636, John Oldham, the same man who explored and reported on the overland route to the Connecticut, was killed by Indians off Block Island. In reprisal, a force of English volunteers went to Block Island where they laid waste to the Indian village there. This only served to infuriate the Pequots. In October Captain John Tilley, was captured, tortured and killed by Pequots after landing on the banks of the Great River. That winter the Pequots continued their hostile activity and Fort Saybrook at the mouth of the river was virtually under siege. By spring of 1637 it was clear that the Pequots were on the warpath.

Urgent steps were taken in new Dorchester to prepare to defend the town. The trainband was readied and the palisado was enlarged and reinforced. Using the high bluff of the Rivulet (the Farmington River) that runs into the Connecticut River near the town’s center as the southern base, the settlers designed an extended parallelogram running about 443 yards north along Sandy Bank above the Connecticut, then 280 yards west, consisting of a wide ditch and an inner earth rampart embedded with a palisade of tree trunks. [To this day that place is called the Palisado Green, and Palisado Road runs through it.] This roughly square half-mile of fortress must have required a huge effort for this small number of villagers. but its existence must also have provided great comfort in that dangerous time.[12]

On May 1 the decision was made to launch a pre-emptive strike against the Pequots, and an expeditionary force of ninety men was recruited from the three river plantations. New Dorchester contributed 30 men and the expeditionary force’s commander, the experienced soldier, Captain John Mason. We don’t know if Thomas was in this group.

On the dawn of May 26 the force with its Native allies approached the fortified Pequot town of Mystic Fort [near the present site of Mystic Port, Connecticut]. They had not been detected and their attack would be a nearly complete surprise. When they were spotted by a Pequot sentry, they rushed up to the palisade, pushed their muskets through the gaps between the poles and fired a volley just as the Indians were waking. Then with swords in one hand and rifles in the other they charged the two entrances to the fortress. The Indians were in disarray, but did their best to defend their town. But their arrows were no match against the rifles and swords, and the English were protected by quilted coats that were effective armor against arrows. On the other hand, the English were outnumbered and might well have lost this battle.

Captain Mason saw the danger and ordered his men to set fire to the village. Less than an hour later the fight was over. Though the Pequot fought bravely and to the last man, they either burned to death or were shot while attempting to escape the flames. Perhaps four hundred Pequots were killed--men, women, and children alike. On the English side, only two men were killed and about twenty wounded. Even the Indian allies of the English, though enemies and victims of the Pequots, were horrified, and said that English retribution was excessive. Those English who witnessed the event were haunted by it for the rest of their lives.

Some of the remaining Pequots moved west toward the Hudson River and escaped, at least temporarily, from the English. The rest were mopped up by another Massachusetts force under Captain Israel Stoughton. Those who were captured were loaded aboard a sloop nicknamed “Charon’s ferry,” taken out into Long Island sound and thrown overboard. The final battle in the war took place in a swamp fight near Quinnipeag, later called New Haven. Afterward, the Pequots were completely dispersed and ceased to be a threat.

The New Dorchester contingent arrived home on Friday, June 3. News had already arrived of their victory and the welcome was ecstatic. They were spotted coming slowly up the Great River seeking the entrance to the Rivulet along the wooded left bank. They poled up the final stretch to the ferry landing of the little settlement and stumbled up the bank into the arms of their families and friends. They had only been gone for 24 days, but they had been exhausting and dangerous days. Now this motley band of Puritan amateur soldiers had become in these few days triumphant and seasoned warriors. The next morning all the community gathered to give thanks to God for the victory and for removing the threat of attack and massacre from their lives. Of course, the returning men also made claim to their soldier’s pay, 1s 3d a day for ordinary soldiers.

Settling In During this year and the next, the settlers concentrated on building more permanent homes, and in 1639 built their first meeting house and church in the center of the Palisado [marked today by a marble monument to these early settlers]. Thomas Gunn had been granted a prime home lot near the center of the new settlement, about a mile north of the Palisado and Meeting House. With the Pequot menace gone, it was no longer considered a risk to be that far away from the fort. [Thomas’s lot was officially recorded in 1640, around the time the other original grants were recorded, though these dates depended on when the settlers brought descriptions of their land to the recorder rather than on the actual date of the grant, which could have been as early as 1636.]

As was customary in Puritan settlements, to keep homes clustered close together for protection and yet provide generous grants of land, Thomas’s property was a very long but narrow lot, 12 rods [198 feet] wide, backing onto the Great Meadow and the River on the east and to the west running beyond the main road, which ran parallel to the River from the Palisado north to Rock Hill. Beyond Rock Hill Thomas held more land, along what came to be known as Gunn’s Brook. To the south his house-lot was bounded by that of Thomas Holcomb and to the north by Thomas Stoughton, whose stone house still existed in the early 1800s. [It was torn down in 1809.][13] His land continued on the east side of the Great River.

Since Thomas Gunn’s house must have been similar to his neighbor’s, here is a description of the Stoughton house, built in 1666: It had two parts, one built of stone and the other of wood. The stone portion was probably the oldest and stood parallel to the road. In later years it was referred to as the Old Stone Fort. Its walls were constructed of heavy, uncut stones, and there were two diamond-paned windows, set in lead. Numerous portholes were located up near the eaves of the high peaked roof. At the northern end of the house there was a gigantic chimney and at the east, or back of the house (facing the river), was a heavy oak-framed door.[14] Thomas remained close to his friends. Thomas Hoskins’s home lot was just north of Stoughton’s and Robert Dibble’s land was just four lots south of Holcomb’s. These locations were determined largely by the places they had built their shelters into and along the Sandy Bank in that first year. Each one claimed a strip of land running back through the rich Great Meadow from the river to the west.

The result was that the settlement took the shape of a line of about forty-five homesteads along the Great River from the Rivulet running toward the north. The common or main road ran from the Palisado at the Rivulet through the western end of each strip of homestead, becoming a crude village street. The home lots were between four and five acres, with a width of 10 to 20 rods (55 to 110 yards). We know that Thomas held land there by 1639 because he made an exchange of meadowland with his neighbor Thomas Stoughton on 11 January 1640. [The Great Migration Begins, 1778] Thomas came to own a total of 219 acres, making him one of the larger landholders in the community.[15]

The size of a householder’s holdings depended on his social status, which in turn depended on several things. Wealth was significant, as well as education and family background. But a man of character and intelligence could hold high rank regardless of his lack of wealth or pedigree. Families of low status got lots at the extreme ends of the main street. The upper class had the choice spots near the center, and all others were scattered in between.[16]

It was a good location for a settlement, with nearly 1000 acres of rich meadowland. The Great Meadow stretched about two miles along the River just below a low bluff called Sandy Bank at the back of Thomas’s home lot. Sequestered Meadow was further upstream and Plymouth Meadow was on the south side of the Rivulet. Rocky Hill was at the northern end of the Great Meadow, and there they quarried good red sandstone for the construction of their homes.

This had been land cultivated by the Natives living along the river, the Matianucks, Podunks and Scantics. But war with the Pequots and, more devastating still, a plague (probably smallpox) had ravaged these Natives so that by this time there were probably no more than about 300 left. They were no longer able to care for their land, and were not considered a menace by the Europeans. For that first generation the relationship between the two peoples must have been fairly amicable. Across the river, opposite the Great Meadow, the Podunks had a stockaded fort and were somewhat more numerous, but under the leadership of Uncas they remained friendly to and were frequently allies of the English.[17]

This was a settlement bounded by two rivers, the Great River to the east and the Rivulet (the Tunxis, now called the Farmington River) to the south. A ferry across the Rivulet was essential, and one was in operation from the earliest days, and another ferry crossed the Great River north of town opposite Rocky Hill. Among the settlers there were men trained in the building trades: a surveyor, a blacksmith, and brick- and stonemasons. So these first settlers had the skills necessary to build sturdy homes in the English tradition (stone and clapboard). (Log cabins did not begin to appear until the 1640s when Swedes settled in Pennsylvania.)

These homes had timber frames, with a minimum of foundation on the bare earth and a sharply pitched roof. The beams and joists were made of oak, as in England (even though other woods were available and more easily worked). [These homes were so sturdily built that a few of them are still standing in Windsor today, such as the original part of the misnamed Filer House.] They soon learned that it was best to build their chimneys using field stones, brick or the local red sandstone, and to use wooden shingles for their roofs rather than the more combustible West Country-style thatch. [George Phelp’s new house burned down in October of 1640.] They also adopted an Essex building style, using clapboard or weatherboard to better protect them from the harshness of the New England winters.

Unfortunately, the settlers were unaware of the dangers of building too close to the rivers and many lost their homes in a flood in 1638. Afterward, they built on higher ground.

These homes were small, unpainted, two room affairs with low ceilings and small windows. They usually stood in a sunny clearing because the roof shingles rotted in the shade. The house generally faced south, and in front of it, shielded from northern winds, was the kitchen garden, and farther away the orchard. Behind the house but far enough away not to be endangered by sparks from the house’s chimney, sat the barn. Trees were difficult to chop down with the tools available, so trees were girdled to kill them and gardens and crops were planted among them. It must have been rather a dismal sight to see hundreds of dead trees everywhere.

Typically the houses consisted of two rooms--a parlor and a hall or kitchen, divided and heated by a central chimney, and a loft reached by a steep, narrow stairway next to the chimney. By raising the roofline they could convert the loft into upstairs rooms. A lean-to could be added to the rear of the house to provide a larger area for the kitchen. There were no rooms with assigned functions, no bedroom, as such, no dining room, no bathroom. Indeed, there would not even have been a chamber pot, or “looking glass,” as it was called. Regardless of the weather, everyone relieved themselves in the privy outside. The loft was for sleeping but also served as storage space. There were no closets; the little clothing they had was packed in chests or hung from pegs on the walls. Normally, there would be no room for privacy. The hall was the place where life within was truly lived. That was where meals were cooked and eaten, where the family worshiped and worked, and at night it served as a bedroom. The fireplace dominated this room.

As the family and its possessions expanded, so too did the house. One of the first additions was a true kitchen, sometimes called a “keeping room.” The hall then became the “best room,” where guests could be entertained. Next might come a lean-to at the rear, which in some houses became the kitchen and in others a storage place for tools and dairy equipment. The house would have been sparsely furnished, with benches, stools and chests to serve as chairs, and bedrolls or “shake-downs” that could be rolled up during the day rather than beds (at least during the early years). The family would have eaten from a long board or pair of boards nailed together and standing on trestles close to the fireplace. It was not called a dining table but the board table. So, to “sit at the board” meant to eat, and a hired hand or paying guest would expect both “room and board.” Diners paired up, sharing a common trencher (a wooden tray about ten inches square and depressed in the center like a soup bowl) and a common wooden drinking cup or leather noggin. They would use spoons and pointed knives to spear the food, but there would be no forks (which did not appear until the eighteenth century).[18]

Within a few years the town had some eighty houses located every hundred or so yards from their neighbors. These were flanked by outhouses, barns, vegetable gardens and orchards. Such large numbers of dwellings would have presented some logistical problems. For instance, since each house with a single fireplace would burn fifteen to twenty cords of wood a year, the town would have burned at least 48 acres of standing timber every year. Much time must have been spent collecting and hauling wood, and chopping it into lengths that would fit the fireplace. And as time passed, the further they would have to go for their firewood. The town’s cemetery was established in 1636 on the river bluff in the south-west corner of the Palisado, where it can be found today.

Thomas Establishes a Family Now that Thomas was a land and home owner, and a respected member of New Dorchester, it was time for him to find a wife and start a family. He may have known his future wife since the days of the voyage, or perhaps she arrived in Dorchester later. We don’t know her name or who her parents were. But it’s likely they were married sometime in 1637 or 1638, quite possibly in the new meeting house inside the Palisado. By the fall it was clear that his wife was pregnant; that must have been a good year for Thomas and for the entire community. A girl child was born to them the following summer, and they named her Elizabeth. Sadly, she died a few months later on the 22nd of August, 1640. But before long his wife was pregnant again, and the second child, Deborah, was born on the 9th of August the following year. [Because two of Thomas's daughters, and a granddaughter by Deborah, were all named Elizabeth, some have guessed that was also the name of Thomas's wife.] The third child, Mehitable, was born two years later on the 28th of July. The only son, John, was born on the 8th of July, 1647. Fortunately, John and the two girls survived this and the next awful years when over sixty of the townspeople died.

Thomas Gunn (1605-1681), died aged 76 years Thomas's wife (1605-1678), died aged 73 years Deborah (1641-1695), died aged 54 years Mehitable (1644-1720), died aged 76 years John (1647-1726), died aged 79 years

Thomas was in his mid-thirties and a well-established man in this community, now renamed Windsor. His home must have been enlarged, not only to accommodate a growing family but, perhaps, boarders as well since there is an indication in the records that he took in lodgers. There is speculation that Thomas kept a lodging-house, as on "Dec 10, 1659 the townsmen approved that Thomas Gunn should entertain as a tabler [one who boards others for payment], Capt. Thomas, in his family for this winter."[19] Soon after, he "had liberty to entertain Isaac Holt in his family one quarter of a year, but no longer, without approbation." A fifth child, the second Elizabeth, was born on the 14th of August, 1649. One can imagine that, being the baby of the family, she was a special joy to her father and mother. Unfortunately, this child died too, on the 3rd of January in the winter of 1655. She was 4 years old.

They had been nearly twenty years in Windsor, and Thomas was now referred to in the community as Goodman Gunn (a title of significant respect given only to men and women held in high esteem among the townfolk). But things were changing for the worse as far as Thomas was concerned. Not only had they lost their last child, but the town had tripled in population to 160 households, over 700 individuals. There had been some bitter and divisive disagreements regarding a new preacher and the creation of a new meeting house for the dissidents. The town was getting crowded, and perhaps Thomas did not feel it to be as friendly a place as it once was. Whatever the cause, he began to think about moving on; two of his oldest friends were thinking the same: Aaron Cooke and George Phelps.

When in 1662 a road was built from Windsor to the new upriver settlement of Westfield, Aaron, George and Thomas petitioned for land there. The first allotments were not made until 1666, for occupation in the following year. In January of 1667 the grants were confirmed and the land was to be settled with families by 10 November of 1668. Thomas purchased land in the Cooper tract (the first permanent grant of land had been made to Ensign Thomas Cooper in 1658), and he had a home lot (6 acres) on the south side of the main street, east of Taylor avenue, the first lot west of Little River. It’s possible he arrived in Westfield with his wife and son, John, as early as May of 1667. We know his friend Aaron opened a tavern in the town the following year, in March of 1668.

Thomas’s two daughters married Windsor men before the family moved: Deborah married Timothy Thrall in 1659 and Mehitable married David Ensign in 1663. By 1667 Deborah already had three children (the fourth would be born on May 1 of 1667) and Mehitable had two. Another inducement for Thomas to move on may have been that Deborah and Timothy needed land and a home of their own, because Thomas gave them his home lot and most of his property in Windsor when he move with his wife and son to Westfield.

This small community of early Windsor settlers will remain intimately linked by association and by marriage for generations. Many new American lineages were established there by Thomas’s children: Deborah, Mehitable and John. For example, Edward Griswold was one of the early settlers of Windsor, and his son George will be the grandfather of Hester Griswold, the wife of Daniel Gunn, born in 1687 in Westfield to John, the only son of Thomas. John himself will marry a daughter of John Williams of Windsor. Another of John’s sons, Aaron, marries Esther Dewey, granddaughter of Thomas Dewey of Windsor and a member of the Dorchester group. Reuben Gunn, a great grandson of Thomas, marries Mercy Stiles, a great granddaughter of John Stiles, a founder of Windsor and member of the Saltonstall party. Even two and a half centuries later, in 1877, Christopher Conrad Gunn, a 3rd great grandson of Thomas will marry Helen Caroline Alford, a 3rd great granddaughter of another of Windsor’s early settlers, Benedict Alford.

Continue to "The Move to Westfield".


1. American Centuries, View from New England: Background History Essays for Teachers:

2. Kent C. L.; Donna Siemiatkoski, and Robert T. Silliman. The Settlement of Windsor, Connecticut(Commissioned by The Windsor 350th Anniversary Committee, Reprinted by The Windsor Historical Society, 1993) p. 1.

3. Avery, p 2.

4. Avery. p 8

5. The Freemen of Massachusetts Bay, 1630-1636 (The Winthrop Society,

6. Thistlethwaite, Frank. Dorset Pilgrims: The Story of West Country Pilgrims Who Went to New England in the 17th Century (Interlaken, New York: Heart of the Lakes Publishing, 1993), p. 103.

7. Thistlethwaite, p. 104-05.

8. Avery, p 10.

9. Thistlethwaite, p. 109.

10. Thistlethwaite, pp. 109-10.

11. Thistlethwaite, p. 111.

12. Thistlethwaite, p. 116.

13. Stiles, Henry R. The History of Ancient Windsor (New York: Charles B. Norton, 1859), pp. 149-71.

14. Stiles, p. 156.

15. Thistlethwaite, p. 263.

16. Hawke, David Freeman. Everyday Life in Early America (New York: Harper & Row, Publishers, 1988), p. 18.

17. Thistlethwaite, pp. 133-34.

18. Hawke, pp. 55-60.

19. Stiles, Vol. I, p. 82.

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