Adjacent to the beautiful square in downtown Woodstock is the 1927 Woodstock Theatre. The theatre's site has been home to a movie theatre since 1911 when the Princess Theatre was built. It was closed in April 1927 to begin construction of the Miller Theatre at the same location. The new theatre opened that November as a 1,000 seat venue complete with vaudeville stage, Bartolo theatre organ and balcony. It was converted to show "talkies" in 1929 and the first talking picture at the theatre was "Syncopation" featuring Fred Waring and the Pennsylvanians.

Over the years, the theatre operated under several different companies. In 1979 the theatre was split in half, providing two auditoriums, each having 301 seats. The balcony was converted to projection booth, manager's office and storage. 
 
Classic Cinemas acquired the Woodstock Theatre in 1988. Immediate renovations included installing larger screens, Dolby surround stereo sound and decorative aisle lights. In late 1991 a new marquee was created to resemble an historic marquee. It now casts a golden glow over the street at night, contributing to the ambiance of Woodstock's historic downtown.                 

 More improvements were made by Classic Cinemas in late 1998. Wider and more comfortable seats were added to both auditoriums, reducing the total number of seats to 462. Other improvements included new carpeting, floor tile and wall decor in the auditoriums as well as lobby décor.

One of the highlights of the theatre's history was the filming of Groundhog Day, a romantic comedy starring Bill Murray and Andie MacDowell. The theatre was used as a film location -- the Alpine at which the character played by Murray attended a movie. Each year the theatre helps the City of Woodstock celebrate Groundhog Day with free screenings of the film. The theatre also is featured on tours of the film's locations. On Sunday, February 4, 2001, a plaque was dedicated to the theatre, honoring it as one of the sites used in the movie.

On May 23, 2002, the Woodstock Theatre opened two additional screens by expanding into the building next door which turned out to be the Beverly Theatre from 1912. At the same time, the restrooms were completely redone, enlarged and made accessable. The box office now has two ticketing stations. All auditoriums have been equipped with digital sound and HPS-4000 surrond sound systems.