Obadiah was born in Springfield, Hampden, Massachusetts.
"Obadiah Cooley son of Benjamin Cooley born 7 mon. 27 day 1645."
He married 9 Nov 1670 Rebecca Williams. He died 3 September 1690, in Springfield.
"The earliest reference to Obadiah Cooley in the town records is that made concerning his assigned seat in the Meeting House in 1662/3, when at the age of sixteen he sat "Below y Pillars on Y North Side." He was twenty-four years old when he married. It seems likely that he was a member of the militia organized in the raid on Springfield in 1675 during King Philip's War, for he was then nearly thirty years old; but no record of military service for Obadiah Cooley has been found. In spite of statements to the contrary in The Longmeadow Centennial, neither Obadiah Cooley I nor Obadiah Cooley II ever maintained residences in Longmeadow. Obadiah Cooley I lived in Longmeadow, probably, during the years after his father Benjamin Cooley, removed there (about 1660), until he established his own home, which was in the village of Springfield. Benjamin Cooley's other four sons lived in Longmeadow; Joseph the youngest son removed from there to Somers, Conn., about 1730. The first grant of land made to Obadiah Cooley in 1664 (given as 1665 in the Longmeadow Centennial) was for 35 acres. From a description of this grant (Burt, Vol. I, p. 320), it is evident that this 35 acres was part of the division of the land between the present villages of Thompsonville and Warehouse Point, Conn. Obadiah never lived on this property. The home of Obadiah Cooley was the tract bounded north by the "Way to the Lower Wharf," now York Street; south by Mill Street; and west by the Connecticut River. Obadiah Cooley II occupied this same homesite. Concerning Obadiah Cooley II's homesite, the following identification of it as the same as that owned by his father is taken from the Town Records.
In 1673, Obadiah Cooley and David Lombard, who lived on opposite sides of the Way to the Lower Wharf (now York street) had "liberty granted, forsecurity of their own and the common fields to make a fence cross the highway to the lower wharf with a gate for passage through, who inconsideration thereof, are to have the privilege of the herbage of the said way to themselves, so long as they shall maintain such fence and gate tosecure the fields."
We who weare apoynted to took after the highways in this Towne being Informed that Obadyah Cooly had Incroached upon the high ways wee who weare appoynted did upon the 7th day of June 1700 take a veiw of his sd Obadyah Coolys fence and we did find he had Incroached upon the highway at the lower end of the Towne by his howse with in the gate (this was the gate at the east end of the lane to the lower wharf.) about e one rod in bredth and for som roads in length we did therefore order him to remove his fence in unto a stake we set up right to the second post from his gate and so it is to run straight about a foot from the corner of his Barn e, etc.
The Obadiah Cooley home lot is not so identified on Burt's map of early Springfield. On this map, the Obadiah Cooley property is divided into two properties, the northern section described as "Two lots each 22 rods broad, running back to Mill Lot granted to Samuel Wright Jr. and Roger Pritchard, sold to Thomas Bancroft"; the southern section is described as "The Mill Lot of 17 acres."