Founded in 1955 by Lawrence Hager, Jr. and other theatre buffs, TWO staged The Man Who Came to Dinner at Southern Junior High. Despite being well received by the public, TWO had no permanent home or source of income, so the group disbanded in 1959. In 1967, former members reunited to participate in the Owensboro Festival of Arts, producing a reader's theatre production of Antigone. This program was such a success, that TWO was reformed and reorganized. At first, the troupe staged productions in school auditoriums and found a short-term home in the basement of the Rudd Hotel.
In 1973, Mayor Waitman Taylor offered the Old Trinity Centre, formerly home to the Trinity Episcopal Church and acquired by the City in 1972, to TWO as a permanent home. Trinity Centre is registered as an historic landmark. Built in 1875, it is the oldest example of Gothic architecture is Western Kentucky. As well, it is the oldest brick church building in Owensboro.
In the early 1990's, play productions were moved to the Riverpark Center. In 1999, Trinity Centre underwent a major renovation that allowed productions to once again be staged in its intimate auditorium. The ambiance of Trinity Centre provides a unique experience for theatre patrons.