In 1776, with wife Phebe, he was living in Scituate, RI. Four years later, June 16, 1780, he buys for thirty pounds, fifty acres of land in the Chippenhook section of Clarendon township, Rutland Co, Vt, from Capt. Abraham Salisbury, whose wife was Zilpha Westcott. This farm adjoined the George Wescott farm at the southwest corner. Salisbury had been made captian of the local militia in 1777, and in 1781, Oliver served in his company for "the defense of the frontiers of Vermont." The company pay-roll shows he was paid for thirteen days service and eighteen miles. He was number 141 on a list of 392 men who before February 2, 1781, had taken the freeman's oath in Clarendon. In the census of 1790, he is enumerated with two males over sixteen years of age (one of whom was himself) one male under sixteen, and two females over sixteen (females under sixteen were not counted). On March 13, 1790, Oliver sells land in Chippenhook to his nephew George Wescott, again February 22, 1798, he sells land to Oziel Smith, and March 26, 1799, sells to his son Johnson, both "of Clarendon," for one hundred dollars, "one certain tract of land or parcel of land lying and being in the west part of Clarendon (Chippenhook), north of James Eddy." Eddy's wife was Mary Salisbury, daughter of capt. Abraham and Zilpha Westcott Salisbury. Johnson Wescott on the following day, March 27, 1799, conveys the same land by deed to his uncle Thomas, who, a year later, April 4, 1800, sells it to Thomas Black. (Stukely Westcott, Vol. 2, Pg. 174, 1939)

1790 Vermont Federal Census, Rutland County, Pg 38
Wescot, Oliver: 02-01-02-00-00
Males +16: 2 Oliver, Ephraim
Males -16: 1 Johnson
Females +16: 2 Robey, Hannah

1800 Vermont Federal Census, Clarendon, Rutland County
Wescott, Oliver: 21001-11111
Males -10: 2 ?? ??
Males 10-16: 1 ??
Males +45: 1 Oliver
Females -10: 1 (Youngest daughter recorded is 13 years)
Females 10-16: 1 Sarah, Mary
Females 16-26: 1 Robey
Females 26-45: 1 Hannah
Females +45: 1 Rhoda (mother)