He was very fond of his family and friends.

Although reserved and silent in ordinary company, he was very agreeable in conversation, and had a delightful wit.

Some of the very greatest men of his time have left on record their estimate of his greatness.
Thomas Jefferson said of him: "There is old Roger Sherman, who never said a foolish thing in his life." Theodore Sedgwick said: "He was a man of the selectest wisdom.
His influence was such that no measure, or part of a measure which he advocated, ever failed to pass." Fisher Ames said that if he were absent through a debate and came in before the vote was taken he always voted with Roger Sherman, as he always voted right.
Patrick Henry said that the first men in the Continental Congress were Washington, Richard Henry Lee, and Roger Sherman, and, later in life, that Roger Sherman and George Mason were the greatest statesmen he ever knew.

This statement, published in the life of Mason, was carefully verified for me by my friend, the late William Wirt Henry, grandson and biographer of Patrick Henry, as appears by a letter from him in my possession.* [Footnote] *I attach a passage from Mr.William Wirt Henry's letter, dated December 28, 1892.
"I am glad to be able to say that you may rely on the correctness of the passage at page 221 of Howe's Historical Collections of Va.
giving Patrick Henry's estimate of Roger Sherman.

It was furnished the author by my father and though a youth I well remember Mr.Howe's visit to Red Hill, my father's residence.