The native Americans who settled in the area would construct weirs for trapping fish on the Ware River.

"[3] In 1716, a tract of land which was slightly more than 11,000 acres (4,500 ha) in size was granted to John Read.

He leased out the land and did not sell 1-acre (4,000 m2) until after his death, when he bequeathed a gift of 200 acres (0.81 km2) to serve as a ministry lot.

As time passed, the town of Ware grew up around the old Congregational meeting house and later became a small center of local manufacturing and commerce.

[3] In 1729, the first grist and sawmills were built on the banks of the Weir River by Jabez Olmstead, eventually becoming part of the Ware Millyard Historic District.

At this point, the Ware community was making the transition from an agrarian economy to an industrially based society.

The post Civil War era (1860s–1900s) brought a new prosperity to the now established textile mill town.

By the 1920s, however, the company began to decline due to lack of modern machinery and movement of industry to the south.

[5][citation needed] In 1922, it was affected by the New England Textile Strike, shutting down the mills in the town over an attempted wage cut.

Shortly thereafter, the company sold its interests to three "cotton men"—Lawrence W. Robert Jr., Edward J. Heitzeberg, and Paul A. Redmond—all with close connections to Alabama Mills, which owned factories in the South.

A public mass meeting was called that evening and plans to raise the necessary cash in order to forestall what appeared to be the imminent ruin of the town were formulated.

[citation needed] The town gained lands in the late 1930s as part of the construction of the Quabbin Reservoir.

Today, the town is home to most of the Winsor Dam and its spillway, and the Goodnough Dike, both of which lie within the Quabbin Reservation.

The reservation lands within town include two islands, the former Little Quabbin Hill and Mount Lizzie, neither of which were covered by the waters of the reservoir.