Connecticut’s First Town, the Friendly Debate Continues

By Carla Charter

CONNECTICUT-If you want to become involved in a friendly historical debate with Connecticut friends, you might want to casually ask them which is the oldest town or city in the state. These towns, Wethersfield, Windsor and Hartford were all established in the early 1630’s.

According to Hartford Historical Society “Historians and fans of their home towns have been debating for years which town came first. It all depends on what criteria you use in determining who came first, is it the arrival of people or a declaration from a governing authority.  One thing all three towns agree on, the indigenous people were the first to establish communities in the land we now call the state of Connecticut, ‘according to the Connecticut Historical Society.

Wethersfield believes it’s the first intentional English town in the Connecticut Colony with the earliest date of record is August 30, 1634, although the settlement was probably established earlier. Wethersfield is not only the “most auncient towne,” but also the inspiration for the settlement of the Connecticut Colony through their founder John Oldham who was born in England in 1592 and migrated to Plymouth from England with his sister, Lucretia. Eventually he petitioned for the right to remove from Watertown, MA and settle at Pyquag, later called Wethersfield, where Native Americans had hosted a recent visit of he and several men. A month following his return to Watertown, MA John Oldham’s brother-in-law, Jonathan Brewster heard of Oldham’s accounts of the lush Connecticut Valley and called on William Holmes to establish a trading post for the Plymouth Trading Company at what would become Windsor.

The right to remove from Watertown, MA to Wethersfield was officially issued on May 6, 1635 and to remove from Dorchester, MA to Windsor on June, 3, 1635, both granted by the Massachusetts Bay Colony. Oldham, along with his settlers, did not wait until the approved word was granted and instead left for Connecticut with the intention to establish a permanent settlement in the summer 1634.

Wethersfield celebrates 1634 as its settlement year, based on a group of men termed “adventurers”,  a seventeenth century term for speculators or traders, under the leadership of John Oldham who held “adventurers lands” in Wethersfield.  Although Massachusetts Governor John Winthrop ‘s Journal notes that Oldham and a group of three others went overland to the Connecticut Valley to trade in September of 1633, they did not stay, and Wethersfield does not acknowledge this year as its founding date.

Windsor believes they are Connecticut’s first English settlement, established in 1633. In 1631, a delegation of sachems from the lower Connecticut valley region travelled to the English colonies in the Massachusetts Bay area seeking protection from the Mohawks (west of Hudson Valley) and the Pequots (Long Island Sound) in exchange for land. English interest in this arrangement did not coalesce until the Dutch established a trading post in Hartford sometime in the summer of 1633. Hartford therefore can claim to be the first European settlement based on the Dutch fort “House of Good Hope” that was established in the South Meadows area of Hartford sometime in the spring/summer of 1633.

What we do know is that on September 26, 1633, a group from Plymouth Massachusetts led by William Holmes sailed up the Connecticut River past the Dutch Fort in Hartford, establishing a trading post in Windsor and selling there.  From that date forward, English people have occupied this site, which has grown into the vibrant community we know as the Town of Windsor today.

We have this date because Governor of New Amsterdam Walter Van Twiller wrote a letter of complaint about the Plymouth group to Massachusetts Bay Colony Governor John Winthrop. From period accounts, we know Windsor traders farmed, repelled a Dutch attack (Van Twiller raised a force of 70 men who tried but proved unable to dislodge the Plymouth traders in Windsor), assisted Native Americans suffering from epidemics, offered sustenance, canoes and guides to Massachusetts men who eventually settled in all three river towns, and occupied this trading post continuously for four years.

On May 6, 1635, the Massachusetts Court granted the inhabitants of Watertown permission to remove themselves to settle elsewhere.  These folks would eventually settle Wethersfield.

On June 3, 1635, the Massachusetts Court granted the same liberties to settlers of Dorchester who removed to Windsor, the first families to settle in this region.  So while settlers of what would become Wethersfield received their permission to create a new settlement before settlers of what would become Windsor did, this was blanket permission to establish a town, not settlement of a town.

Connecticut histories by Benjamin Trumbull (1797), J. Hammond Trumbull (1886,) Albert Van Deusen (1961) and the like all mention the September 26, 1633 founding date for Windsor, Connecticut’s first English settlement.

The Connecticut State Capitol building includes the Holmes settlement of Windsor as one of its vignettes in stone with nothing analogous for Wethersfield.  We base our claim to first English settlement status on the fact that Windsor has been continuously occupied by English speaking people since September of 1633.

The friendly debate over which was the first community in Connecticut, may never be fully resolved. However, it will also be an interesting topic of historical conversation.

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