The village of Monson Center lies at the center of the town.
The first colonist to settle in present-day Monson was Richard Fellows, who in 1657 was granted 200 acres of land by the Massachusetts General Court. He built a tavern along the Bay Path, which was the primary route from Springfield to Boston, and which ran through the northern part of Monson. It was the first house built between Springfield and Brookfield, but the tavern was short-lived; within a year or two, Fellows abandoned it for fear of attacks from local Native Americans.
The first permanent settlers arrived in 1715, and in 1735 the town of Brimfield was incorporated, and included present-day Monson within its boundaries. The eastern part of the town later separated, and was incorporated as the town of Monson in 1775. The town was named after Sir John Monson, president of the British Board of Trade and a friend of Massachusetts governor Thomas Pownall.
In the 19th century and early 20th century, mills were built along the Chicopee Brook, which runs south to north through the center of the town. One of the most successful industries during this time was the woolen mills, which were operated by industrialists such as Joseph L. Reynolds, Dwight W. Ellis, C. W. Holmes, and S. F. Cushman. In addition, Heiman & Lichten operated a successful straw and felt goods factory on Main Street.
Monson was also known for its granite quarries; the first quarry was opened in 1809, east of present-day Margaret Street. It was used for a short time by the federal government to supply stone for the Springfield Armory, and was later sold to Rufus Flynt, who opened a commercial quarry on the site in 1825 with five employees. By 1900, the quarry was operating under the name of W.N. Flynt Granite Co., and had expanded to almost 500 employees. The quarry continued in operation until about 1935.
On June 1, 2011, an EF3 tornado crossed through the center of the town, causing $11.9 million in property damage, which included 238 damaged buildings, 77 of which were damaged beyond repair. Several town landmarks were damaged or destroyed: the First Church of Monson and the Unitarian Universalist Church buildings each lost their steeple, the historic 1900 Holmes Gymnasium, once part of Monson Academy, was destroyed, and the town office building, built in 1925 as the first Monson High School, was damaged beyond repair and demolished in 2013.