The hotel was built in when Santa Paula was growing and prospering as an oil town and was headquarters to Union Oil. The Tudor-Craftsman hotel was designed by famed architects Burns and Hunt and funded by a consortium of twenty-five wealthy townsmen each of whom wanted one thousand dollars for its construction.
It was erected directly opposite the train depot to provide accommodations to the many newcomers lured to the area by the burgeoning oil and citrus industries, and to provide a gathering place for Santa Paula's growing high society circles.
Beginning in the s, Hollywood discovered the valley hamlet of Santa Paula. Many Universal film professions either stayed at the hotel or ate in the restaurant during these early years. In later years, western stars like Randolph Scott visited the hotel while on location.
Because of its popularity, the hotel struggled to house visitors to Santa Paula. After city leaders sold the hotel in , the Glen Tavern's new owner, Charles Estep, converted the hotel's unused attic space into a third floor for guests, completing the conversion around Eventually, as oil money and old Hollywood moved on, Santa Paula settled down into a quieter constancy of agriculture and small-town life Americana. Federal Public Housing Authority leased the property from Estep.
The government then converted the hotel into a woman's dormitory for employees working at nearby Port Hueneme. In , the lease ended and the Glen Tavern once again functioned as a hotel. By the s, the train depot became defunct, and likewise, economic development bypassed the town. For the next half-century the hotel endured a marginal existence, alternating owners and uses many times as it slowly sank into flophouse decrepitude until it was eventually rescued by developers with intentions of restoring its original grandeur.
