Dana Point Inn ruins

In 1923, Los Angeles Times publisher Harry Chandler and General M.H. Sherman, Director of the Pacific Electric Railway Company, created a major real estate group to develop what is known today as the Hollywood Hills, Sidney H. Woodruff, already a prominent Los Angeles homebuilder, was hired to lead the project. In 1926, Woodruff, Chandler, and Sherman created the Dana Point Syndicate. They invited other heavy hitters, company presidents, movie producers, and real estate investors, to join them in purchasing 1,388 acres of land, some of which includes the Headlands of today. Promising tree-lined, paved streets, electricity, telephones, sidewalks, water mains, storm drains, sewers, and other amenities, Woodruff built 35 homes and a number of commercial buildings. His crowning structure was to be the Dana Point Inn, a Mediterranean-like resort hotel. After a celebratory groundbreaking in 1930, a three-story foundation was poured and a 135-foot elevator shaft was dug. Unfortunately, the Depression caused construction to halt. Although Woodruff continuously sought financial support through the years, this project was abandoned in 1939. Subsequently, he sold the remaining holdings of the Dana Point Syndicate. Thirty-four of the original Woodruff residences are still occupied.