Thomas Chesebrough was the son of Jonathan Chesebrough and Bridget Minor (or Miner). His headstone says he was 52 years, 16 months, and two days old at the time of his death on April 4, 1807, which indicates he was born January 19, 1755.

He was born in New London County Connecticut (some sources list Stonington while others list nearby Preston). He was married to Joanna Tyler on October 15, 1775.

Thomas served in the Revolutionary War. He enlisted as corporal in Capt. Josiah Boardman's company, Connecticut Line, 1776; served in the New York campaigns and was engaged in the battle of White Plains, New York; he was a sergeant at Fort Griswold, Connecticut, Eighth Regiment, Eighth Company, July 10, 1775.

Thomas's bible and diary were in the possession of Charles Edwin Chese brough ca 1900. Thomas' entries included:

"February ye 10th, 1764, then my brother Jonathan departed this life in the thirtieth year of his age."

"November ye 17th, 1764, Then my honored Father departed this life in the sixty-fifth year of his age."

"April ye 23d, 1766, Then my honored Mother departed this life in the fifty-sixth year of her age."

"March ye 11th, 1776, Then my daughter Polly was born."

"December the 28th, 1777, Then my daughter Anna was born."

"April the 15th, 1780, then my son Jonathan was born."

"December ye 30th, 1781, then my daughter Eunice was born."

"March ye 20th, 1784, then my son Henry was born."

"February ye 9th, 1790 I had a daughter born; she lived about twenty-eight hours and expired; was buried ye 12th day of February."

"My daughter Anna departed this life October ye 17th day, 1803 aged twenty-five years nine months and nineteen days."

According to his will, dated March 6, 1807, he was a shoemaker by trade. It listed the following chldren who were still living at that time: Jonathan Chesebrough, Polly Manchester, Eunice Cornell, and Henry Chesebrough.