In November 1921, a group of graduate students and faculty members of the Department of English organized the Homewood Playshop. Influenced by the little theatre movement which had spread across the United States since 1915, its aim was to supplement course work in drama and to present plays not likely to be seen on the professional stage. The Playshop's first dramatic director and main organizer was Morris T. Cushing, instructor in English; the first President was Frank A. Litz, professor of English. Initially, play practices were held in classrooms, and performances in the garret of the Barn, the auditorium of the Civil Engineering Building, or the theater of the Vagabond Players, in a Centre Street apartment building. The first public performance was in February 1922. Early in 1923, the Playshop performers secured the use of their own building, a white clapboard structure, located between Homewood House and the new dormitories. A $1700 loan from the Trustees turned the building into an excellent little theatre. The first performance given in the new campus theatre was on February 22, 1923. Originally the Playshop was an independent organization, with open University membership, electing a President, Secretary, Treasurer, four directors (dramatic, literary, art, music), and four assistant directors. Morris Cushing, as dramatic director, had the main voice in the group. In 1924, however, a dispute arose concerning the finances and aims of the organization. Mr. Cushing's faction was outvoted, and he withdrew from the group. John E. Uhler, then instructor in English, became the new dramatic director. By 1926 the organization had paid off about half of its debt to the Trustees, but had run up a substantial bill with local businesses. Although the Playshop had a good income, no cost controls had been instituted on the acquisition of supplies and services. As a result, the administration reorganized the Playshop, placing it more formally under the Department of English, and under the control of a Board of Governors appointed by the President of the University. The Board made Dr. Uhler, who had since taken his degree, director of the Playshop (now a paid position) with complete financial authority for the organization. By September 1927, Dr. Uhler was able to pay off all outstanding debts.

Membership in the Homewood Playshop was diversified, representing nearly all departments and divisions of the University. Starting with about thirty members, it had grown to about 200 members by 1924. Later, membership eligibility was extended to some of the other colleges and universities in the area.

Uhler considered the Playshop to be an academic rather than a social activity, and he slightly changed the emphasis of the Playshop to reflect this view. In a 1924 article, he specified that the main purpose of the Playshop was to encourage the writing of plays. As such, he rarely directed any productions himself, usually delegating this responsibility to assistants. His second aim was to provide practice for those who sought to make acting a career. And thirdly, he wished to promote a general interest in drama. Most of the plays performed during this time were written by members of the Playshop. In 1931 Dr. Uhler resigned as director to accept appointment at another university.

He was succeeded by Bryllion Fagin, then instructor and later Professor of English. Around this time the name was changed from the Homewood Playshop to simply the Playshop. Though the Playshop continued to be primarily a tool for instruction, and writing was still stressed, more emphasis than before was placed on acting and production. Fagin also became more interested in entertainment and community service. Audiences became larger, and several prominent Baltimoreans were long time subscribers. Cooperation increased between the Playshop and other little area theaters. Dr. Fagin also expanded previous programs a lecture series featuring outside lecturers and a playwriting contest. Under Dr. Fagin's direction the Playshop continued to present plays not likely to be produced by professional companies, including classics such as "Macbeth" and plays by Sophocles. Since income from subscriptions and ticket sales did not cover all expenses, the Playshop also received money from University funds and private sources.

In 1942 the building housing the campus theater had to be torn down, and the Playshop moved to the Barn, which was renovated; a new little theater was built inside, which the Playshop shared with the Barnstormers, an undergraduate dramatic club. In 1946, the Department of Writing, Speech, and Drama was created, and the Playshop, several professors, and several courses were gradually switched to it from the Department of English. By 1950 the Playshop had 100 resident and 200 non resident members. The Board of Governors continued to direct the activities of the organization. By this time, too, the Playshop had acquired a national reputation for being one of the finest little theaters in the country. In 1953 Dr. Fagin took one year's leave of absence from the University, and, after he returned, he delegated most of his responsibilities to his assistants. He officially retired in 1957. Frances Cary Bowen, instructor of drama, served as acting director from 1953 to 1957, and became the new director in 1957. An assistant director since 1940, she had directed several plays during Dr. Fagin's term. Through 1957 productions continued to reflect the interests of Dr. Fagin, but after Bowen became official director she began some new trends. She emphasized experimental plays, Shakespearean plays, and ancient Greek plays, turning away from original plays. The playwriting contests were discontinued. The Playshop was still used for instruction, but the trend toward professionalism and a more active community role accelerated. Bowen herself was involved in numerous dramatic activities throughout the region. Once Shriver Hall was completed in 1954, some plays were presented there, which allowed for larger audiences and more lavish productions. Ms. Bowen resigned in 1955, due to financial difficulties with the Playshop and a lack of support from the administration. After a review of the Playshop, the administration decided to retain it, but made several changes in its structure. The new director, Edward J. Golden, Jr., was recruited from professional theater, rather than from an academic institution. The Playshop and Barnstormers merged into one company, renamed Theatre Hopkins. The Board of Governors remained, maintaining a link with the Writing Seminars Department and the English Department, but Theatre Hopkins grew more independent. Mr. Golden also began to teach some courses in the Evening College. Theatre Hopkins became more professional and community oriented, and its role as an educational tool for students of drama was virtually eliminated. This new role was formalized in 1966 when Golden assumed additional duties as director of Special Events, and Theatre Hopkins was placed under that office. Golden chose contemporary and experimental plays, but he emphasized established rather than new writers. He was the first director to personally direct all of his own productions. The synthesis with the Barnstormers was never achieved because of the resistance of the students, and they remained an independent organization. In 1969, Golden resigned in order to go into teaching after his proposal for a Drama Department at Hopkins was rejected by the administration.

The new director was Laurlene Straughn Pratt, a member of Theatre Hopkins who was teaching high school at that time. She had been assistant director of the Playshop from 1938 to 1940. Pratt made few changes, but emphasized plays which were seldom produced in professional theatre because they were considered financially risky. She was able to do this because Theatre Hopkins was in a sound financial condition due to University support, and also because the Barn theater only seats 130. Currently the audiences tend to be evenly mixed between University members and community members. Mrs. Pratt has a core group of about thirty actors from which to draw a cast, and actors no longer have to be connected with the University. Currently, Theatre Hopkins is more a service to the community and the University than an aid to learning, as was originally emphasized. However, the organization views itself as a University tradition with over sixty years of association with the University.