Three mothers, Josephine Gregory, Margaret Brown, and Margaret Baker, convinced Mr. I. R. Damon to let them incorporate a school under a Board of Directors composed mainly of parents. The board, in turn, hired Mr. Damon to serve as headmaster. Damon, as the school became known, enrolled 70 students in grades 1 through 12 and was located on Grove Street. In 1938, it was renamed Tamalpais Junior School. Under an arrangement with Frederick Dailey, owner of the Tamalpais School in San Rafael, the school then operated to the 6th grade with the older boys being transported by bus to the Marin campus.

At the August 16, 1939 meeting, the Board of Directors decided to sever that relationship, and the Tamalpais Junior School was officially renamed Town School for Boys. About this time, the Board leased a building at 1464 McAllister Street for $150 a month. Forty students attended through grade seven. Tuition was approximately $270 per boy.

Town first rented, and in 1943 purchased the 2700 Jackson Street property for $40,000. Included in the purchase was a 19th Century Victorian built by Mr. Albert Gallatin, a descendant of a signer of the Declaration of Independence. In its new location, the school became more visible to its community, enrollment increased dramatically, and graduates gained admission to prestigious Eastern and Western preparatory schools as well as local high schools.

Town’s first headmaster was Edwin M. Rich. Known as “Sir” to his students, Mr. Rich was at Town from 1938 until 1957. He was a strict disciplinarian who was nonetheless close to the students. He pitched baseball to the boys at recess, sent personal notes to them at Christmas, and made comments about each of them at Commencement. When he wasn’t writing plays, songs, stories or books, he was whittling plaques for winners of the spelling bees. His wife objected to the wood chips, so he gave up whittling in favor of knitting. Teachers were soon receiving hand-knitted argyle socks as Christmas presents. In addition, Mr. Rich and Mrs. Dorothy Cameron, Town’s music teacher from 1945 until 1973, collaborated on many popular musical productions involving the entire student body. The Edwin Rich era ended in 1957 when he left to become a full-time headmaster at Lick-Wilmerding High School, a position he had held part-time for a couple of years.

From 1957 to 1967, Town had four headmasters: Robert M. Kimball (1957-1962), Dr. Harold E. Merrick (1962-63), Samuel Hazard (1963-1965), and Marshall Umpleby (1965-1967). In 1967, David L. Pratt was hired. Over the next 22 years, Mr. Pratt assembled a dedicated and caring faculty; he encouraged the faculty’s professional development; and he campaigned for increases in teachers’ salaries. The school enjoyed a period of resurgence in the fine arts, music, drama, and athletics. Enrollment soared.

The school’s seventh headmaster, W. Brewster Ely IV, arrived in 1989. He founded the New Teacher Institute as a two-year teacher-training program for men and women planning to make a career in education in either public or private schools. He also created Project Discover, an outreach program for children at risk, with the Boys and Girls Clubs of San Francisco and a consortium of seven independent schools. Values education and character development are also emphasized along with a strong curriculum.

The goals of the school as it moves into the 21st century are continued academic excellence, active support of strong values, student-centered learning, education for a global world, and a strong emphasis on non-academic programs to complement the curriculum.