Originally comprised of land granted in answer to a petition on behalf of the veterans and surviving heirs of the 1690 expeditions to Canada, Winchendon was first settled by European colonists in 1735 and called the Plantation of Ipswich-Canada until it was incorporated in 1764.

Winchendon’s proximity to the Millers River provided waterpower for the development of mills including those used to manufacture grain, wooden products and textiles. One wood product, shingles, was produced in such volume that Winchendon became known as “Shingletown.”

A series of inventions by residents enhanced mill operations, including those of Morton Converse whose company manufactured wooden collar boxes and toys. So successful was Winchendon’s toy industry that it became known as “Toy Town,” a name that it retains to this day.

Along the path of the Millers River, in the western part of town, much of the land is marshy, with several brooks feeding into both the Millers and nearby Otter River. Birch Hill Wildlife Management Area, Otter River State Forest, and Winchendon State Forest are in town.