The first movie theater in Sayville opened to the Sayvillians in August 1911 and was located on Railroad Avenue, adjacent to the current Sayville Theater. It was called the Novelty Theater and had a seating capacity of 400, and adjacent to the theater was an outdoor airdrome with 700 seating capacity. Show admission was 10 cents and on “Feature Nights”, it cost a nickel to attend.

Unfortunately, the Novelty Theater, along with the airdrome, were eradicated due to a fire in 1918. A year later, a second Novelty Theater opened to the public in the same location. In 1930, Prudential Circuit obtained ownership of the second Novelty Theater and the cinema was renamed Sayville Theater. Architects John Eberson and Drew Eberson remodeled the picture palace in 1935, but the second Novelty Theater ceased operations in 1951. The new Sayville Theater was unlatched to moviegoers in 1951, in the exact location where the current movie theater is. 

Sayville Theater had a spacious seating capacity of 1,000 compared to its predecessor, and in December 1981 was developed into a triplex. More renovations were done almost two decades later as the balcony was split, inducing in a four-screen theater in April of 1999, with the upstairs theater notorious for playing blockbusters. The theater was dubbed Sayville Cinemas for many, many years, and currently now under new management, the movie house is called Sayville Theater.

There were three other theaters in Sayville in the 20th century. On Gillette Avenue there was the Crescent Theater, which was built in 1913 by William Mantha, who was a local businessman, but the Crescent Theater’s existence was very momentary as it closed in 1914. The property was dismantled in 1937. There also was the Sayville Opera House, which Isaac H. Green Jr. designed, and the venue opened in 1901. The location was Candee Avenue, directly to the left of the Suffolk County News building.

In 1922, movies were shown daily at the Opera House. A fire decimated the building in 1961 and the venue ceased operations. The current location of where the opera house was is now a parking lot, where on the sidewalk is a bench and a sign listing shops on Main Street, and no more than 60 feet behind Rumpelstiltskin Yarns. That was the spot where the Sayville Opera House was during the turn of the century and into The Roaring Twenties.

There also was the Sayville Summer Playhouse, which was open in the ‘40s and ‘50s. Prior to it being a playhouse, it was an estate, then a country club. Edith Gordon, the country club owner, rebuilt it into the Sayville Summer Playhouse. It was known for theater but also motion pictures and art house films, such as independent movies. The Summer Playhouse was in the current location of Good Samaritan Nursing Home on the corner of Candee Avenue and Elm Street.