Mrs. Josephine Pierpont, a wealthy Ojai socialite, saw the future of automobile travel along the coast and bought the largest tract on the bluff in Ventura.  A woman of quality taste, she hired Julia Morgan, the (architect of Hearst Castle,) to design her home in Ojai.  She commissioned the best commercial architect of that time, Sumner P. Hunt, to create an ultra modern Craftsman- style inn.  The Pierpont Inn opened on September 6th, 1910 with a gala.  The Inn boasted of modern amenities like electricity, heating, and private bathrooms.  The Inn becomes the premiere place for celebrations in Central California. Mrs. Pierpont chose her son, Austen Pierpont, to manage the hotel.

After Austen Pierpont decided to become an architect, Mrs. Pierpont sold the Inn in 1916 before repurchasing it in 1919. By the 1920's, when the Oil Boom brought great wealth to Ventura, it became he private Pierpont Country Club, where all of the most prominent families of Ventura acquired memberships. While Austen had settled his private practice in Ojai, because of the summer heat there he built two English Tudor cottages on the property in 1925 as a summer retreat for himself and guests. These would later become the Rose Garden Cottages. 

As the prosperity of the 1920's wound down, the Inn came up for sale agin. This time Gus and Mattie Gleichmann bought the Pierpont Inn with a $80,000 loan from her father, Ashby Vickers. Mattie's sister, Josephine Vickers, would go on to marry baseball legend, Fred Snodgrass, a member of the New York Giants. Both were very involved in the early management of the Innn. 

Gus Gleichmann was a talented artist himself and drew this map of Ventura with al the local architectural landmarks including every gas station from Pierpont Bay to the Ventura River. The focus on the gas stations illustrates the importance of the Oil Boom and its effects on the economy. During this time, the Gleichmanns' made the first architectural additions to the Inn. They added a second story to the south side of the property and added a family living room with fireplace that would become the Santa Rosa Room. 

During WWII, nearly all hotels in America were converted to hospitals or rest and recreation centers for soldiers. The Pierpont Inn was no different, and Mattie told many stories of soldiers patrolling the grounds during this time. 

Ted Gleichmann, the son of Gus and Mattie Gleichmann, had grown up at the inn and would emerge after his WWII service as a visionary hotelier. 

Ted Gleichmann applied his modern ideas for expansion of the Inn, enlisting his golf associates (who were visionary architects) to help him expand the Inn. He commissioned famous architect Robert R. Jones to design and build the East Wing and a private home for his mother, Mattie (today, called the 50's flat). Today, the 50's flat is eligible for the National Register. Ted Gleichmann also purchased the adjacent house, built in 1935, for his personal residence because of it's convenience. This home later became the Vickers estate and Pavilion. 

Ted actively courted the Hollywood Community with his many social connections. The Pierpont Inn became the place for a quick, quiet, private get-away for the likes of Bing Crosby, Bob Hope, Bogart and Bacall, Fred MacMurray, members of Frank Sinatra's Rat Pack, and many more. Just 60 miles from Los Angeles, it became the place for producers, directors, writers, and actors to 'get-away' from it all. 

When the 101 Freeway came to Ventura, it caused devastating results for the Inn. The Gleichmann family sued the State of California for environmental damages and won nearly $400,000 in this landmark case. The money went to building the West Wing and Bluff House. ted would later incorporate the freeway into his brochures, figuring if you "can't fight 'em, join 'em."

Ted Gleichmann oversaw a large expansion of the dining room to accommodate the popularity of the Inn restaurant and he includes a new room called the Captain's Room. 

Ted Gleichmann passes away, though Mattie will live to be 100.

Spencer and Scott Garrett leased and then eventually purchased the land across from the Inn from Mattie. The Garrett brothers were grandsons of Josephine and Fred Snodgrass, Mattie's sister and brother-in-law. In 1977, they build the Pierpont Racquet Club, a private membership club for fitness and tennis. 

After meticulously caring for the property through the 1980's, the Gleichmann family recognized the historic importance of the Inn, both architecturally and socially, to Ventura County. They pursued landmark status, both to protect the Inn and as a marketing strategy. In 1993, The Pierpont Inn became historic landmark no. 80 for the city of Ventura. 

After owning the Pierpont for 70 years, the Gleichmann family passed the baton to Spencer and Scott Garrett. The Pierpont Inn then became The Pierpont Inn & Racquet Club. Pictured is the official Gleichmann "farewell" portrait. 

The Inn partnered with the Museum of Ventura County to curate original pictures of the Inn and to celebrate its 90th birthday as a county-wide event called the 1910 Exposition. Every historical society in Ventura County was included, along with period costumed living history docents. It was a massive success and created great awareness and community good will. 

The Pierpont Inn applied for and was accepted into Historic Hotels of America, a branch of the National Trust for Historic Preservation dedicated to marketing American historic hotels. it was a great honor and a large community wide celebration became an event. 

The Pierpont Inn restaurant is the longest continually operating dining facility in the history of Ventura; since 1910,, it has never closed.  However, it never had a separate name to give it an identity from the Inn. Spencer decides to name the restaurants 'Austen's.

Then Garretts sell the hotel. The Pierpont Inn then goes into a period of decline as several owners purchased it. However, it remained the choice of brides in Ventura.