The history of The Schoolhouse Theater dates back to 1894. After a hurricane destroyed the original schoolhouse building, a replacement was constructed at a cost of $54.50. It remained at its original Bailey Road location until its move to the Periwinkle address in 1903. There the schoolhouse became the heart of the community until 1964 when it was closed due to the construction of the Sanibel Elementary School.

The schoolhouse would have remained abandoned were it not for the vision of veteran Broadway actress Ruth Hunter and her husband, Philip Hunter. The Hunters bought the schoolhouse and transformed it into an intimate 90-seat theater called the Pirate Playhouse. They presented community theater productions in the truest sense of the word. Virtually everyone who lived on Sanibel at the time found himself (or herself) performing in one of the Hunters’ plays. Then the Hunters retired in 1984 and the schoolhouse once again fell into disuse.

Luckily, two young actors, Robert Toperzer and Carrie Lund, decided to rent the theater and start productions again, bringing the Pirate Playhouse back to life. Due to its overall success, a decision was made in 1991 to build a new, larger Pirate Playhouse further up Periwinkle Way.

After the completion of the new Pirate Playhouse, the former Pirate Playhouse was left vacant until Carrie Lund and her husband, Robert Cacioppo, brought a person by the name of J.T. Smith to Sanibel. With the help of Jean and Bob Wigley and others, J.T. Smith took on the role of Artistic Director at the former Pirate Playhouse, immediately renamed it The Old Schoolhouse Theater, and brought upbeat musical comedies to the island.

Meanwhile, the Pirate Playhouse underwent a few name changes over the years to The J. Howard Wood Theater and then to the Periwinkle Playhouse, which had a very successful run with General Manager Todd Sherman at the helm. Finally, in 2004, the Old Schoolhouse Theater Foundation moved into the facility and renamed it once again (hopefully for the last time!) to The Schoolhouse Theater where the tradition of fantastic musical theater continues today under the Direction of Sanibel Favorite, Victor Legarreta.