The land upon which the village of Cowlesville is situated was purchased in 1818 by Quartus Clapp, who built a saw mill the same year at the foot of what became Mill Street. He built a frame house which stood at the corner of Mill and Main Streets.
In 1826 Mr. Clapp built a grist mill adjoining his saw mill.
The hamlet was known as "Clapps Mills" until 1832 when the post office was established. The first school house was built in 1827. In 1828 Elisha Daggett and Ellis Loomis operated a carding mill. In 1837 John Whitney built a tannery. The first blacksmith in the village was Russell Hoag. He was appointed postmaster in 1832. At this time the name Cowlesville was given to the village at this time, in honor of a Mr. Hiram Cowles who was a clerk for G. B. Rich.
The village's first physician was Erastus Cross. The first building built as a tavern was by Mr. Austin at the corner of Main and Hill Streets in 1840. Cowlesville Furnace was erected in 1844 by Elisha Daggett.