[1] Josephine Pierpont thought the site on a bluff overlooking the ocean could serve the increasing number of automobile enthusiasts who would travel along the Pacific Coast looking for a place to rest.

She felt the inn could serve the increasing number of automobile enthusiasts who would travel along the Pacific Coast looking for a place to rest and enjoy a home-cooked meal.

Josephine's son Austen Pierpont ran the Inn for the first many years, expanding it in 1925 by adding two English Tudor-style cottages surrounded by a lush, garden setting.

[2] After Mattie's husband, professional baseball player Gus Gleichmann, was forced to leave the sport after being injured, they decided to pursue a career in hospitality.

[6] In 1976, Spencer and Scott Garrett (grandchildren of Mattie Gleichmann's sister) leased the then-vacant parcel of land adjacent to the Inn to build one of the nation's first multi-purpose athletic facilities, "The Pierpont Racquet Club".

Tinsel-town notables such as Cecil B. DeMille,[9] Bette Davis, Edward G. Robinson and Charlie Chaplin all took breaks from filming in Hollywood by escaping to the charming location.

[citation needed] The property was also a hideaway for scandalous lovers such as Clark Gable & Carole Lombard and Humphrey Bogart & Lauren Bacall, many of whom, because they were married to others, desired to have their privacy protected.

[citation needed] Local attorney Erle Stanley Gardner authored his "Perry Mason" series in his law office down the road from the Inn and actually used it as a backdrop for many of his novels, particularly in "The Case of the Velvet Claws."