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The Olive Opera House Was Ossining's Other 'Big House'

The Olive Opera House in Ossining was built in 1865 and hosted live and film entertainment.
The Olive Opera House in Ossining was built in 1865 and hosted live and film entertainment. Photo Credit: Contributed

OSSINING, N.Y. -- Ossining is known, worldwide, for Sing Sing Prison.

It has, throughout the years, been referred to as “The Big House.” But there was another "Big House" within our boundaries that brought laughter and entertainment to all who entered its doorways.

The Olive Opera House was the entertainment center of the village for many years. It originally was built in 1865 by Hugh Herringshaw and was the place for live, and later, celluloid entertainment covering a wide array of expressions.

From the 1860s and into the 20th century, the building on the corner of Brandreth and Central avenues offered its patrons everything form lecture programs, minstrel shows and benefit programs to straight dramatic plays.

The curtains rose almost every night of the week and the performers were greeted by enthusiastic audiences who eagerly plunked down their nickels and dimes for an evening’s entertainment. In February 1874, the building was destroyed by fire, with damages estimated at the time to exceed $30,000. Yet, by year’s end the theater was rebuilt and re-opened to the public.

A wide array of professional stock companies graced the stages of the opera house throughout the week, giving matinee performances Wednesdays and Saturdays.

On Saturday nights, aspiring local thespians, acrobats and magicians performed in amateur night competition.  If the performer’s efforts did not meet with the approval of the audience, there would be loud foot stomping on the wooden floors of the balcony. If, by this time, the offending performer did not "get the message" and retreat gracefully, he or she would be pelted with an avalanche of fruits and vegetables.

One local resident who was bitten by the show business bug was Jesse Collyer Jr. (1897-1983), who later became mayor of the Village of Ossining and Town Supervisor. The boy’s father worked as the theater’s property manager and arranged for his son to have a small part in a dramatic play. Flushed with the glow of theatrical success, the young man joined the vaudeville circuit upon his graduation from high school and toured the Hudson River Valley and New England states with a repertory company.

In its heyday, the Olive Opera House featured such performers as May Hope, who was the original owner of the fabulous Hope Diamond, as well as the heavyweight champion John L. Sullivan. Other celebrities included New York City Mayor Jimmy Walker and the legendary actress Lillian Russell. Also appearing was the acclaimed opera singer Madame Nordica from nearby Croton-On-Hudson.

With the passing of the vaudeville era, the opera house turned to celluloid entertainment, complete with live musical accompaniment. At one point, it was one of seven movie houses in the village.

After the Olive Opera House closed its doors to the entertainment world, the building served as the home of the Steward Manufacturing Co., the Community Action Program in the early 1980s and, more recently, a fitness center and karate school on the ground floor.

On the upper floor, current owner, well-known artist Katherine Fan, has her studio along with other local artists’ studios.

In the front part of the old opera house, where the tall windows are in place, a theatrical supply house is in residence, the only remaining touch of the Olive Opera House’s stage background.

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