Ashland’s First Settlers
The General Court of the Colony of Massachusetts made a grant of 500 acres of land within the great bend at “Cold Spring” to Colonel William Crowne in 1662. This was a reward for services the Colonel had rendered for the Colony . The grant included what is now the center of Ashland. The Colonel died in 1687, never having set foot on the land. In July of that year his heirs sold the grant to Savil Simpson of Boston who was a cordwainer or maker of leather goods. Simpson’s home in Boston burned September 16, 1690, which may have entered into his decision to move from Boston to the land in the wilderness. We don’t know exactly when he moved but in the minutes of the Framingham Town Meeting for the year 1709 there is mention of a road from “Mr. Simpson’s farm to the meeting house” and in 1710 he is listed as a Framingham taxpayer. Part of his road is still in use as Fountain Street in Ashland.
Simpson’s home is thought to have been in the vicinity of the Telechron G. E. Factory. There is a memorial in the Revolutionary Cemetery on Union Street stating that is the place he is buried. This was the family burial plot but the burying ground beside Kings Chapel in Boston also claims to hold his remains. Local tradition, however, has insisted he rests in Ashland.
He left no sons to carry on the name but a daughter who married Colonel John Jones. Their home was near the present site of the Pittaway School. Colonel Jones built another house for his son, John near the present location of the Town Hall. This dwelling was close to the mill site which the family developed, which was near the dam at the foot of Myrtle Street.
Ashland Directions – August 1975
 History of the Town of Ashland, Commonwealth of Massachusetts, 1942. Multiple references throughout the page.