Before Europeans arrived, the territory where Middletown now sits was held by the Wangunks on the east bank and the Mattabesetts on the west bank of the Connecticut River. These two peoples shared a common chief, Sowheag, at the time of the initial European settlement in 1650.

In 1646 the General Court appointed a committee to draw up plans for establishing a settlement at Mattabesett. The committee proceeded slowly, but finally, in 1650, the first English families arrived from Hartford, Wethersfield, and Windsor. The new community became officially a town the following year, adopting the name "Middletown" in 1653, a reference to its distance halfway between the mouth of the Connecticut River and Windsor.

The first Africans were brought from Barbados to Middletown as slaves eight years later in 1661. Slavery remained a part of Middletown life throughout the seventeenth and eighteenth centuries; by 1756, 218 slaves — at the time the third largest African population in the colony — lived among a population of approximately 5,44 Europeans.

During the late sixteenth century, many Mohegans from the Hudson River Valley migrated into Connecticut. They were named the "Pequots" by local tribes, meaning "destroyers of men." Sowheag and his tribespeople had intermittent conflicts with the Pequots, and when the English families began to settle, the Mattabesetts and Wangunks hoped the English might help defend against Pequot attacks. This proved groundless, however, since most European settlers viewed all Native Americans as equally dangerous.

Smallpox and yellow fever killed many indigenous people throughout the seventeenth century, greatly diminishing their strength and ability to resist. Gradually, Sowheag was forced to sell most of his territory. By 1672, a committee purchased the remaining Native Americans' lands on both sides of the river, except for 300 acres on the east side and a strip previously reserved for them which extended through what is now Newfield to Sowheag's former encampment on Indian Hill.

In the late 1600s, Middletown covered a far greater area than it does today, extending from what is now a section of Rocky Hill south to Haddam, west to include much of what is now Berlin, and east to include East Hampton and Portland.

The first English families in Middletown faced numerous difficulties. The land had to be cleared, houses and barns built, pastures and fields fenced, and crops planted, tended and harvested. The sheer physical labor was enormous. The Puritan religion governed the community, creating a strong, yet strict, society. There were fourteen offenses in Connecticut for which the death penalty was prescribed, including witchcraft, blasphemy, cursing or smiting of parents, and incorrigible stubbornness of children.

There also remained throughout most of the seventeenth century a constant fear of attack from savages who were understandably violent after having their land taken and many of their people killed. Middletown and other Connecticut towns had their own militias, or train bands, and held regular training days. Colonial statute required Middletown to have a force consisting of at least eight armed men and a sergeant acting as guard at any assembly for public worship. The militia kept watch around the meeting house, a structure 20 feet square enclosed by a palisade.

During the fifty years before the guns of Lexington, Middletown merchants developed an extensive trade between New England and the West Indies. Middletown enjoyed booming times while the trade lasted. So closely was Middletown's economic life tied to the sea that, by the outbreak of the Revolution, one third of the population was engaged in maritime trade and merchant activities.

Colonial Towns of Connecticut Links