Although its oldest element is the cemetery (established 1688), most of its buildings were built in the late 19th and early 20th century.

[1][2]: 2 Simsbury, originally the location of a Native American settlement called Massaco, was acquired by English colonists in the 1650s, and settled beginning in the 1660s.

Hopmeadow Street (now signed United States Route 202) developed as the major north-south route on the west side of the Farmington River, and the town center grew near an early ferry crossing.

The majority of the district's surviving 18th and early 19th-century buildings are houses, most of which have been adapted for commercial use.

The district derives its character from a larger number of late 19th and 20th-century buildings, general of a civic or commercial nature.