Wolcott House is named for Governor Roger Wolcott (13 July 1847 - 21 December, 1901). Arriving on the Dorchester Shore in 1678, Roger Wolcott's family was dedicated to public service in New England in the eighteenth and nineteenth centuries. Roger Wolcott's great grandfather (also Roger, 1679-1767) was Governor of the State of Connecticut from 1751 until 1754, and his grandfather, Oliver Wolcott (1726-1797), was a member of the Continental Congress and a signer of the Declaration of Independence. Governor Wolcott's father, Joshua Huntington Wolcott, moved from Connecticut to Boston in 1850 and subsequently built a house in Milton on Canton Avenue.

Roger Wolcott was elected to the Massachusetts House of Representatives, then to the office of Lieutenant Governor of Massachusetts, and finally Governor of Massachusetts, which post he held from 1896 through 1898 (gubernatorial elections in The Commonwealth were annual until 1900). Among the policies for which Governor Wolcott is remembered is his firm support for the Spanish American War, for which he raised both funds and troops. In 1899, he declined to run for Governor because he thought his health was failing, and, indeed, he died not long thereafter. A friend to many of the most prominent people of The Commonwealth and beloved by its citizens, he was buried in Mt. Auburn Cemetery in Cambridge. A memorial statue of Governor Wolcott was commissioned by his friends. Executed by Daniel Chester French, the marble portrait is now located in front of a mural depicting scenes from the Spanish American War in the Massachusetts State House. There is also in the State House a portrait of Roger Wolcott by Frederick Porter Vinton. Among Governor Wolcott's associates was Edward Wigglesworth, a member of Milton Academy's Board of Trustees. Roger Wolcott's excellent example of leadership and friendship inclined the trustees of The Academy to name their third dormitory after him.

Construction of Wolcott House was completed in 1900. The first House Head was Albert Weeks Hunt, who was also the only member of the house staff, as was the custom in the early years of all the Academy houses. In those years, as well as during the war years, the responsibilities now shouldered by the house faculty were typically carried out by senior boys. This tradition lives on in the work of the Senior of the Night and Class II proctor. In the central stairwell of the house can be seen the names and photographs of all the boys who have lived in the house from 1900 until the present. These pictures serve as daily reminders of the long and proud history of the house. In similar fashion, the names of every House Monitor has been engraved or painted on the panels in the lobby and the first floor corridor across from the Ward Room.

The seal adopted for Wolcott House was the crest of Roger Wolcott's family. The seal appears on all house communication, duty lists, and articles of clothing that the House Council commissions each year. A painting of the Wolott family crest hangs over the hearth in Devens Room. This painting was presented to the house by the Wolcott family in 1984, the year in which Mr. and Mrs. Flaherty became House Heads. The inscription under the crest reads:

nullius addictus iuare in verba magistri
called to swear upon the words of no teacher

The hexameter line is, of course, from Horace (Epistulae 1.1). The quality this thought represents is as fitting for the students of Wolcott House as it is for the Wolcott family. In Horace's day, philosophical schools did not allow students to deviate from the teachings of their master, nor to study under more than one master. Thus, it was bold for a prominent intellectual to declare that he would follow no orthodoxy on its own authority, but instead judge by reason which ideas were the best. Horace's insistence on independent and rigorous examination of ideas is heeded to this day in Wolcott House, where it sometimes seems that no idea goes untested.

In 1930, Charles Buell, then House Head, constructed the annex. This replaced the second floor faculty apartment as the House Head's quarters. Mr. Buell was a demanding teacher and coach, but he was also determined to make his house a safe and comfortable place for students to live. In order to express these seemingly paradoxical qualities essential to the character of a boarding school teacher, Mr. Buell affixed to the chimney of the annex an emblem featuring a fierce bear taking care of its cubs. The cramped and archaic gothic script around the annulus reads:

Der Bär ist sonst ein böses Thier [sic: sc. "Tier"]
The bear is usually a vicious animal,

Aber ganz anders ist er hier
but he is entirely different here.

Tritt ein es wird sich lohnen
Come in; it is profitable to live

In seiner Höhl zu wohnen
in his den.

During the War Years, pictures and memorials of students and alumni from Wolcott House who died in military service were placed on the walls of the Ward Room. Included among these is the citation of Benjamin A. G. Fuller II, a recipient of the Distinguished Service Cross.

In 1950, the class of 1943 presented the shipstrike clock in Ward Room, still the most accurate in the house, in memory of William Foster, a Wolcott boy and Navy man who died in 1949. This clock rings the standard Navy watches, with study hall, for example, starting at 7 bells and ending at 3 bells. The tree that stands across from the Devens Room on the quads was planted by the family of John Fraser, Milton Academy class of 1982, after he died in a motorcycle accident in 1986.

The original house included neither Mr. Buell's annex (mentioned above) nor the w ing in which the Ward Room and the faculty apartments are now located. These were added later, in the course of many renovations and restorations that have been carried out over the years. The most substantial work done recently was in 1975. This project included installation of the steel frame interior, conversion of part of Devens Room into two new student rooms (100 and 101), and re-fitting the space at the top of the building into the present fourth floor. In the summer of 2005, more modernization followed: furniture was replaced, all student rooms were carpeted for the first time, a new fire-detection system installed, and the basement area was renovated as a recreation and study area.

The roll of Wolcott House Heads spans more than a century with only nine names: Mr. Albert Weeks Hunt (1900-1927, 1941-1944), Mr. Charles Buell (1928-1941), Mr. H. Allen Sherk (1944-1953), Mr. John Torney (1953-1971), Mr. David Roak (1971-1972), Mr. Wolfenden (1972-1974), Mr. Charles Burdick (1974-1981), Mr. Bryan Cheney (1981-1984), and Mr. Thomas J. and Mrs. Francis Flaherty (1984-2003). The pictures of House Heads who served for more than a decade are displayed in the Devens Room.

Members of Wolcott House perpetuate the spirit of those who have gone before them in their seriousness of purpose, friendliness and leadership. There are also many house traditions that symbolize the character of the house. Among these is that the members of the house and its staff always refer to the rooms in the house by the names of those they memorialize. Ward Room, where the pool table is located, is named for Andrew Henshaw Ward, a former Master in Milton Academy. Hunt Room, directly ahead as one enters the house, is named for Albert Weeks Hunt, the first House Head of Wolcott House. Devens Room, where the computers are located, is named for William Lithgow Devens, Milton Academy Class of 1961. A similar tradition that persists to this day is that members of Wolcott House always wear proper trousers and a shirt with a collar when they attend house dinners. This tradition of polite neatness surpassing the rules of The Academy dates to the 1930's and 1940's, when the Wolcott boys distinguished themselves by keeping a white handkerchief in the breast pocket of their blazers. "Roofball" also deserves mention. This game, played according to a complex set of rules handed down from one class to the next, originated at least as early as the 1940's, as attested by house alumni.

Perhaps most dear to the members of the house, and one of its most evocative traditions, is the exact wording of the request made by the Senior of the Night at the end of each meal that the members eat together. He calls for "a moment of silent thanks, because we have so much to be thankful for."