Located north of Hartford on the Connecticut River, Windsor was the first permanent settlement in the soon to be Connecticut Colony and the home of Thomas Holcombe. In 1633 a group from Plymouth established a trading post at the meeting of the Connecticut and Farmington Rivers. A year later, the first group from Dorchester, Massachusetts established themselves just north of the trading post. Others from Dorchester would follow and a foothold in Connecticut was established.

North-central Connecticut prior to 1625 showing tribal settlements along the Connecticut River in the area of future Windsor.

Connecticut is divided in half by the Connecticut River, known as "The Great River". Connecticut, in Mohegan means "the long river" (originally quonehtacut, quinnehtukguet, or connittetuck). To the west lies the Hudson River and Housatonic River valleys inhabited by the Mohawk and Iroquois. To the east lies the Thames River valley inhabited by Pequot. Four main tribes made up the "River Indians" in the Connecticut River valley. They were the Podunk on the east shore and Poquonock, Saukiog and Tunxis on the west shore.

After scouting out the area in 1635, the Reverend John Warham, members of his congregation and a few others established a permanent settlement at Windsor. Officially founded in 1636, the town was briefly called Dorchester. The Warham group had some disagreements with Governor John Winthrop’s Massachusetts Bay Colony over land distribution, governing procedures and religious policies. Although discouraged by the Colonial Government to settle in Connecticut they, non-the-less, set off into the wilderness to start their new settlement. Windsor was the first town established in Connecticut. The river gave the settlers access to the coast and supplies, but it was far from the Plymouth and Massachusetts colonies and defined the edge of the frontier in the 1635.

From the Windsor Historical Society website . . . Land and water shaped Windsor's settlement patterns from its earliest years. For the local River Indians, the Connecticut and Farmington Rivers were transportation corridors to the interior fur trade, also providing fish for sustenance and fertile floodplains for seasonal agriculture. The River Indians existed between two stronger warring groups, the Pequot and Mohawk Nations who exacted regular tributes from them in exchange for an uneasy peace. In 1631, River Indians journeyed north to English settlements at Massachusetts Bay and Plymouth, inviting English settlement in the Connecticut valley with descriptions of fertile lands and abundant wildlife. Their hope with such an alliance was to strengthen defenses in their area.

There was little interest from the English in Massachusetts until 1633, when word reached them that the Dutch had established a trading post in what is now Hartford. Now, the pressure was on to establish an English outpost on the Connecticut River, a major transportation artery with headwaters far to the north, providing access to promising fur trade. 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.  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. For text sources and additional information, go to www.windsorhistoricalsociety.org.

A plan of Windsor, 1633 - 1650, depicting the first settlers.  A drawing from The History of Ancient Windsor, Connecticut

Thomas Holcombe and his young family would be part of the group from Dorchester that came to Windsor. He would first live on one of the lots that lined the Connecticut River but soon move north to the outskirts of the settlement to a place called Poquonock.

From the Holcombe Website . . . In the Summer of 1635 some Dorchester people had already reached the river and sat down at the place where William Homes, and others of Plymouth, had erected a trading house and made preparations for bringing their families and settling permanently; and in November, 60 persons with a large number of cattle, traveled from Dorchester and arrived in safety at the river, after much tribulation. During the first winter the sufferings of these persons were intense and they lost nearly all their cattle. Some individuals wandered back to Dorchester and others avoided starvation by dropping down the river and taking refuge in a vessel at anchor at the mouth. In the spring of 1636, Reverend John Wareham left Dorchester and came to Windsor, Connecticut, bringing his flock, including Thomas Holcomb, with him . . . 

A drawing of the Thomas Holcombe house made in the early 1800's.

There are approximately 138 names listed as founders of Windsor; most of the names are male so it seems that those listed represent the heads of household. 60 came in the first group from Dorchester in 1635. Some single men, carpenters and tradesmen, arrived on the ship Christian that same year and many of those stayed on at Windsor. Most of the rest arrived from Dorchester the next year in 1636. The Holcombe family is related by marriage to a great many of these original families. Some notable Windsor residents include:

• Mathew Grant; Mathew was the 5th Great-Grandfather of Ulysses S. Grant. Mathew was on the Mary and John and as town clerk was an important documenter of Windsor history. Much of the early family histories of Windsor exist because of Mathew. Though somewhat convoluted, the Holcombe and Grant families are intertwined through various marriages.
• Mathew Griswold and son Roger Griswold; Mathew was the Great-Grandson of another Mathew Griswold who came to Windsor with his half-brother Edward (and Edward’s three sons) and settled at Poquonock. He later moved on to Saybrook. Mathew the younger was active during the Revolutionary War in many capacities and later served as Governor of Connecticut.
• Roger Griswold would also serve as Governor. Earlier in his career, as a congressman, he was noted to have brawled with another congressman from Vermont. He also proposed succession of the New England states during the Jefferson administration. This branch of the Griswold family had many marriages with the Wolcott family (see below), while the other branch, led by Edward Griswold, had many marriages with the Holcombe family.
• Major John Mason was a British officer who settled at Windsor. He led the Puritan effort against the Pequot tribe and was considered “one of the most trusted men in Connecticut.”  His descendants include James Garfield and other notable people.
• Oliver Phelps; Oliver was the Great-Grandson of Windsor founder, George Phelps. Oliver was born at Poquonock but spent his childhood in other parts of Connecticut and Massachusetts (as his father died when he was three months old). He served as Deputy Commissary of the Continental Army, supplying the troops for the duration of the war and was commended by General Washington. As with the Griswold family, there were a number of Holcombe / Phelps marriages.
• Roger Wolcott, son Oliver Wolcott Sr. and Oliver Wolcott Jr.; Roger was the Grandson of Windsor founder Henry Wolcott (Roger’s father, Simon was five years old on the voyage to America).  “Henry Wolcott stands first in a list of the inhabitants of Windsor . . . and was probably, after the pastor, the most distinguished citizen of Windsor.” Rodger was a weaver by trade, active in colonial life and served as Colonial Governor of Connecticut.
• Oliver Wolcott Sr. participated in the French and Indian War, was a signatory to the Declaration of Independence, served in the Continental Congress and was a General in the Revolutionary War.
• Oliver Wolcott Jr. succeeded Alexander Hamilton as Secretary of the Treasury and served under President’s Washington and Adams. He resigned in 1800 due to unpopularity, and a particularly vitriolic campaign against him in the press in which, among other things, he was falsely accused of setting fire to the State Department building. He also served as Governor of the State of Connecticut and presided over the adoption of the 1818 state constitution.

Two of Thomas Holcombe's sons would move west to Simsbury and raise large and prominent families in the new settlements away from the Connecticut River but one son would stay on at Windsor. In addition, a number of daughters would marry local men and raise their families in the town. Holcombe descendants can still be found there today.


Research Notes: There is an abundance of information available on the web about Windsor and its history. For this report, information was gleaned primarily from the Windsor Historical Society and the Holcombe Family website.

This post is one of a series about the places my ancestors lived. From time-to-time, additions to the series are made. For an overview of all of all of the towns and places covered and links to each story, go here . . .