The town of Middlesex was granted by royal charter on June 8, 1763, by New Hampshire colonial governor Benning Wentworth.

Shady Rill is rolling, mostly lowland where three brooks-Herrick, Martins, and Patterson, each named for a local family, converge with the North Branch which runs south to Wrightsville and Montpelier.

The village of Putnamville is located along the town's eastern border along the North Branch River.

Wrightsville, just south of Putnamville, was once a sizable settlement with nearly 30 built structures, and several mills.

The Wrightsville Dam, built by the Civilian Conservation Corps 1933-35 in response to the 1927 flood, caused that settlement to be disbanded.

The farmer and his wife immediately walked their property to take stock of their flock.

The farmer spotted a bear and killed it, soon afterward his wife called out that she sighted one and he shot that one, the couple returned to the barnyard and spotted a third bear-this one eating another of their sheep, and the farmer shot that bear as well.

Dairy farming, sheep herding (for wool), logging, orchards and maple sugaring have all been part of the town's economy.

Following the end of World War II, the town slowly transitioned to becoming a place to live for people who worked elsewhere, mostly in Montpelier.