The Wappinger were one of these groups, composed of eighteen bands that were organized not formally as a tribe, but more akin to an association, like the Delaware.

[3] One of the Wappinger bands, the Massaco, lived near, but mostly west of, what became known as the Farmington River, in the area that would become known as Simsbury and Canton,[4] the latter as of 1806.

"[6] Settlers in Windsor forested and farmed in the area, but did not settle in Massaco permanently for a number of years.

In 1642, the General Court of the colony of Connecticut ordered that:[7] the Governor and Mr. Heynes shall have liberty to dispose of the ground uppon that parte of Tunxis River cauled Mossocowe, to such inhabitants of Wyndsor as they shall see cause.

Five years later the General Court issued another order:[8] The Court thinks fitt that Massacoe be purchased by the Country, and that ther be a Committee chosen to dispose of yt to such inhabitants of Wyndsor as by the shalbe judged meet to make improuement therof... but there is no record of land grants arising from this order.

[9] In 1643, John Griffin and Michael Humphrey started a tar and turpentine business in Windsor.

A few years later, a Massaco Indian named Manahanoose started a fire which destroyed tar belonging to Griffin.

As he was unable to pay this amount, Manahanoose was instead ordered by the Court to either serve Griffin or be exchanged for Black slaves.

The General Court awarded a land grant of two hundred acres to John Griffin in 1663.

[10] In 1670, John Case, along with Joshua Holcomb & Thomas Barber, presented a petition to the General Court, requesting that Massacoe become a town of the colony of Connecticut.

The war extended through parts of four colonies, with Simsbury on the western edge of the conflict.

In the days leading up to the war, they ordered settlers to keep night watches and to work in the fields in armed groups of at least six.

[22] In 1707, Daniel Hayes, then aged twenty-two, was captured by indigenous people and carried to Canada.

Eventually, he was sold to a Frenchman, who learned that Hayes had skill as a weaver and put him to work in that business.

[23] On Tuesday, December 20, 1859, the two-story Patent Safety Fuse factory located near the center of town exploded, killing seven women and one man.

At the western foot of the mountain, the Pinchot Sycamore, the largest tree in Connecticut, grows near the Farmington River.

[26] The town is often considered a bedroom community for the nearby city of Hartford, Connecticut, which is a 20 to 25 minute drive from Simsbury Center; however, many residents also commute to other towns and cities within the west-central Connecticut region.

[citation needed] After the complete destruction of the town in 1676 during King Philip's War, there were three late 17th to early 18th century nucleated resettlement communities: East Weatogue (also called East Simsbury), Simsbury Center, and Terry's Plain.