The Headlands Inn was built in 1868 as a small barbershop on Main Street in Mendocino. The second story was added in 1873 to provide living quarters for the barber, John Barry, and his family. In 1884 the building became a "high class" Restaurant, The Oyster and Coffee Saloon. The owner at that time, W.J. Wilson, used the upstairs as an annex to The Wilson Hotel.

George Switzer purchased the house in 1893 and moved it to the present location on the corner of Howard and Albion Streets. It was transported by horses pulling the house over logs which were used as rollers. More recently the house was known as The Bessie Strauss House. Bessie and her husband, John, bought the house in 1924 and resided here until 1979. Four of the Inn's rooms carry the names of these previous owners.