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The Opera House was built in 1909 by U.S. Martin, who served as Shepherdstown's mayor. Within that same year, it was sold to the Musser family who installed one of the earliest motion picture projectors. The Opera House ran nightly, often showing as many as three different films each week. In 1928 the Opera House became the first motion picture theatre in West Virginia with sound, enabling it to show the newfangled "talkies."

The Mussers closed the Opera House in 1956, and it sat dark and silent until it was purchased by Pam and Rusty Berry. After an extensive renovation following the Department of the Interior guidelines for the restoration of historic structures, the Berrys reopened the Opera House in February of 1992 and began showing American independent and foreign films. In 2004 they added new lighting and sound systems to accommodate live musical and theatrical performances onstage.

In October, 2010, Lawrence and Julie Cumbo purchased the building and business with a vision to take it to the next level. As a filmmaker, Lawrence wanted to preserve the theater's cinematic tradition, but he knew music had to be another cornerstone of Opera House culture. Since then, continual light and sound system upgrades, an expanded back stage, and revamped green room has allowed this vision to grow into one of the area's finest music and film venues.