In 1922, when the New Canaan Playhouse was built, current day Elm Street (then Railroad Avenue) was vacant land, except for one resident on the south side. A group of local men, The Village Improvement Company, recognized the need for a playhouse. Their proposal included the opportunity for each and every resident to become a stockholder.
The cupolaed building was designed by local resident, Calvin E. Kiessling. Kiessling’s design, the red brick and white trim, suggesting a modified colonial structure, established the style for the future buildings that eventually filled in both sides of Elm Street. The building had a frontage of 58 feet on Railroad Avenue (Elm) and extended back 100 feet with flanking passageways on each side used in conjunction with the fourteen exits in addition to the exits off the main lobby. The original plans also called for two stores at street level. The auditorium itself was originally 56 feet wide and 76 feet deep, with a seating capacity of 400.