Dudley was only eighteen years old when his father died and left him the southern part of the homestead farm in Stonington. He and his wife lived there until 1796, when Dudley and his brother Gurdon moved their families to Chenango Co., NY. Dudley first bought property in Norwich, Chenango Co., NY on 29 DEC 1797 (Deed Book A, p. 95). The family remained there for many years. Dudly sold his land in Norwich in 1814 (Deed Book R, p. 422), and resettled in Tioga Co., PA. He purchased property in Delmar Township and latter in Shippen and Gaines Townships. By 1820, he was operating a sawmill on Mill Run near the town of Gaines, PA. Later, Dudley built the first sawmill on Pine Creek in Shippen Township, an area now encompassed by Gaines Township. With the help of his sons, Dudley, Wheaton and Russell, he carred on an extensive lumbering for many years.

Dudley served as a Lt. Colonel in the 67th Regiment of the New York militia during the War of 1812. He was referred to as Col. Dudley Hewitt in the histories of both Chenango Co., NY and Tioga Co., PA.

The 1790, 1800 and 1810 census indicate that Dudley and his wife had at least 4 sons and 3 daughters.