He was bound in many ways by ties of affection and sympathy to thousands of men, women and children throughout the Commonwealth of MA. There is a statue of him in the State House in Boston, erected by popular subscription.
Of him it has been written by Bishop William Lawrence, who was his friend for more than forty years, "There was that about him which defies analysis, which eludes definition, but which is found in those rare characters, who, like Philip Sydney, Chevalier Bayard, or Robert Louis Stevenson, gain our confidence, win our admiration, kindle our affection, and who, in their unconsciousness, make us conscious that we are in chivalric company. He was a practical New Englander with a dash of idealism without which no New England Character is complete. From boyhood he gained the affection of all sorts of people. He drank deep, in poems, history, and the Bible, of Chivalric life. In form and countenance, in presence and atmosphere, he was of nature's noblest." (From Roger Wolcott by William Lawrence).
The following eulogy was delivered 1901 in Boston by U.S. Senator Henry Cabot Lodge of MA: "We here have one of the rare instances of a family which starting in America with a man of fortune and good estate always retained its position in the community. In the main line at least it never encountered the vicissitudes which attain nearly all families in the course of two hundred and fifty years. The name never dropped out of sight, but was always borne up by its representatives in the same place in society as that held by the founder. More remarkable still, in almost every generation there was at least one of the lineal male descendants of the first immigrants who rose to the very highest positions in military, political and Judicial life. The list of judges, governors, cabinet officers and members of Congress in this pedigree is a long and striking one. From the days of the Somersetshire gentlemen to those of the present generation, which has given a Governor to Massachusetts and a brilliant Senator from Colorado to the United States, the Wolcotts both as soldiers and civilians, have rendered service to their country, eminent as it has been unbroken. War and Statecraft were in the blood of this race, and can we wonder that they have found fitting exemplars in our own time? It is not a name made illustrious by some single ancestor in a dim past and suffered to rust unused by descendants who were content with the possession of a trademark. Here is a long roll of honor where the son felt that he would be unworthy of his father if he did not add fresh lustre to the name he bore by service to his state and country, either in the hour of trial or in the pleasant paths of peace."