"The earliest reference to Samuel, characteristically enough, is in a lawsuit. This was described previously under his brother, Daniel. Samuel must have gotten disgusted at losing this case, and struck out for the north - the first Whittemore to leave the Charlestown area - as we find several references to him in early New Hampshire Province records. Whether he married in Dover, N. H., or before he left Charlestown, has been impossible to determine."
"Samuel did not like it very much up there, and he returned to the vicinity of his relatives within a few years, for a list of inhabitants of Charlestown for tax purposes includes Samuel Whittemore on 11 March 1678."

The next time Samuel is in Court is in 1685, for cutting and carrying away wood from John Mousall's lot in Charlestown.
On 15 Oct. 1686, Samuel appeals to the Superior Court at Boston from a judgment against him in a land boundary dispute with John Mousall of Charlestown.
Samuel is in a lawsuit with Capt. Bowden, in 1690, over a horse.
The foregoing shows Samuel to have been a pretty tough customer; in fact, downright quarrelsome.1894