Smiley’s Schooner Saloon and Hotel was established in 1851 and has been in continual operation in the same stalwart and storied building ever since. We’ve yet to find an older bar West of the Mississippi.
The saloon is believed to have been built for the energetic young Captain Isaac Morgan. Captain Morgan arrived in Bolinas (or Jugville as it was known then) in 1849. Those were gold rush days, days of growth. Those were days when one gambled with one’s dreams and then watched them either shatter and splinter or be crafted and honed into realities.
Morgan applied his considerable energy to diverse and lucrative projects, including an apple orchard, schooner building and, of course, his saloon. The Captain lived in the house on the Lagoon side of Smiley’s and watched his bar survive the 1860’s temperance movement when many of the town’s dens of drinking iniquity closed down. The 1868 records of the Bolinas division #8 of the “Sons of Temperance” does not list Captain Morgan, even though most of the other prominent and influential men in town were members.
A few years later though, in 1872, shortly before he went back east to find a wife, we surprisingly find him listed as the Chaplain of the “Independent Order of Rechabites” which sponsored temperance lectures.
After Morgan left, though few records survive, we know Niles Ogden ran the bar for forty years. There is no record of the pub closing after the great quake of ‘06. Quite the opposite was true. Business picked up because the two nearest establishments where one could also quaff lightning libations, The Flagstaff and the Del Mar, were unceremoniously dumped in the Lagoon.
The 1920s found most drinking establishments in the nation closing due to Prohibition. Smiley’s didn’t close. She just put on a little window dressing. Her windows were painted black (a condition repeated during World War II for fear of Japanese bombers). One window remained clear through which a passerby could glimpse a barber chair and other barbershop paraphernalia. Customers would enter the barbershop then proceed through a second door into the bar. Business must have been good, old timers recall the rum runners kicking up a lot of dust roaring in and out of town in their new-fangled automobiles. Legend has it that Al Capone spent one summer in Bolinas before he was beset by hard times in federal prison.
Over the years, the name of the saloon changed with its ownership: Jim Redmen’s Saloon, Ed Knott’s Bar, etc. The Italian immigrant, Ismaele Biachini, bought the place in 1955. Ismaele, Smiley to his friends, called the landmark “Smiley’s Bar and Bait.” Where the barbershop had been there was now a baitshop.
Attorney Vernon Bradley was a more recent owner, turning the management over to his mother, Sue, who ran the place with a firm hand through the high living 70s. It was a pizza parlour and saloon under Bradley.
In the 80s, the now ancient establishment was owned by Robert Glenn, a professional publican and man of impeccable taste. Glenn restored the now somewhat tattered building, refurbishing it from top to bottom with the finest materials.
In 1990 Glenn turned the helm over to Don Deane. Deane’s background included being a Marin County Probation Officer, social service agency executive and publisher of the Coastal Post newspaper. Under Deane’s tutelage, Smiley’s became known up and down the state and across the country when the town of Bolinas is mentioned.
In 2015, Smiley’s Schooner Saloon passed into new hands. New owners Leila Monroe and Ashley Huck are committed to continuing and building on the tradition of great music and community entertainment that has defined Smiley’s for decades.