Smiley's Schooner Saloon in Bolinas, the oldest business in Marin County, has a new owner, Leila Monroe, a 35-year-old San Francisco lawyer, the first woman in its colorful, 163-year history. That's the news in this happily isolated coastal hamlet, ending months of rumor and speculation, but it isn't the story. The story is that in a town famously mistrustful of outsiders, no one is calling her a carpetbagger. Quite the opposite, in fact.

"People are receiving her very well," said 72-year-old Don Deane, who's owned and operated the aged Wharf Road watering hole for the past 25 years. "She is a wonderful and potentially powerful ally for the community."

That is quite a statement in a countercultural haven whose residents are so reclusive they tore down its Highway 1 road sign so many times that the last one is on permanent display in the Bolinas Museum.

For an idyllic village that would like to remain as anonymous as possible in today's world of tweets and texts, its reputation as a hippie haven for poets, writers and artists is endlessly fascinating to people far beyond the borders of Marin County.

In June, a New York Times travel article, headlined "Bolinas, Calif., the Town That Didn't Want Company," described the place as "a sort of suburban preserve" that quietly markets itself as "a bulwark against change."

Three years ago, Deane, a former Marin probation officer who's been a foster parent to dozens of at-risk teenagers over the past three decades, was having a hard time keeping the bar and its six guest rooms in the black.But the good people of Bolinas can't stop change any more than they can halt the Pacific Ocean waves that roll over Duxbury Point on their way to Bolinas Beach, one of the best surfing spots on the Marin coast.

Since he wasn't getting any younger and could no longer continue to defer maintenance on the decaying building, originally built in 1851 by a sea captain named Isaac Morgan, he put Smiley's on the market for something like $1.6 million.

Smiley's had survived the 1906 earthquake, Prohibition and any number of fires, floods and calamities, earning the distinction of being one of only 14 bars in the state in continuous existence for more than a century.

But unless a buyer came along with the wherewithal to fix her up, the old girl was destined to fall down around its loyal customers' ears.

There were no prospects during the waning months of the recession. But, with the economy now on the upswing, several potential buyers came forward recently, making multiple offers.

Leila Monroe, the new owner of Smiley’s Schooner Saloon, spent her childhood in Maui and coastal San Diego County. "My parents were hippie
Leila Monroe, the new owner of Smiley's Schooner Saloon, spent her childhood in Maui and coastal San Diego County. "My parents were hippie surfers," she says. (Alan Dep/Marin Independent Journal)



Deane ended up selling to Monroe, an outdoorsy millennial who grew up in Maui, graduated from Georgetown University Law School as an ocean conservation lawyer, worked for the National Resources Defense Council and has been coming out to Bolinas to surf for the past 10 years.

"I really love it here," she said the other day, sitting at a vintage Pac Man table game in a corner of the bar. "I love the ocean, and the protection and planning the community has done for this place," she added, referring to the environmentally and socially progressive Bolinas Community Plan that townspeople adopted in 1975.

Smiley’s Schooner Saloon in Bolinas needs structural and interior work, but "it’s going to be fun," said new owner Leila Monroe.
Smiley's Schooner Saloon in Bolinas needs structural and interior work, but "it's going to be fun," said new owner Leila Monroe. (Alan Dep/Marin Independent Journal)

Trim and athletic, Monroe has sea green eyes, a wide smile and shoulder-length brown hair that was still wet from a morning of surfing with a friend. She had on a pair of faded red Vans, a sweater and light blue jeans. Mr. Fox, her feisty little rescue dog, was busily barking at the languid local canines, who did their best to ignore him as they lounged around on Smiley's weathered wooden floor while their owners, perched on bar stools, shot the breeze and sipped early afternoon beers.




Under Deane's stewardship, Smiley's has earned a reputation as a devoted supporter of live music, one of the few places in West Marin that has local musicians playing on Thursday, Friday and Saturday nights.

Patrons leave earlier this month at Smiley’s Schooner Saloon in Bolinas. The business is one of one of only 14 bars in the state in continuous
Patrons leave earlier this month at Smiley's Schooner Saloon in Bolinas. The business is one of one of only 14 bars in the state in continuous existence for more than a century. (Alan Dep/Marin Independent Journal)

"For a little town that's pretty isolated, to have a thriving, vibrant music scene is a little unusual," Deane said.

As if Monroe's environmental bona fides weren't enough, it seems almost too good to be true that she's also the founder of Project AMPLIFI, a nonprofit that stages concerts and events with independent musicians to raise money for worthy grassroots organizations and to heighten awareness of issues facing artists and others of modest means.

For example, on Dec. 4, Grammy nominated singer Carolyn Malachi performs at a concert at Code and Canvas on San Francisco's Potrero Hill. The evening includes a panel discussion on "How to maintain a robust music community in the midst of the affordable housing crisis." Monroe envisions events like that at Smiley's.

"I think a lot of artists would be excited to play here," she said, mentioning that she has already shown the saloon to rocker Lukas Nelson, Willie's son, a close friend of hers from high school in Hawaii.

"He's been sort of an adviser to me," she said. "Smiley's is similar to a place where he performs on Maui, a little surf side bar where we have intimate concerts."


Monroe plans to build on the music scene that's already happening at Smiley's, adding a small stage and making the configuration of the room more conducive to audiences and performers.

But her pressing concern is the desperately needed repairs that must be made if Smiley's is going to stay standing for another decade, let alone another century and a half.

The foundation is crumbling on one side of the two-story building, there's dry rot in the guest units, the bar needs sprucing up, the kitchen will have to be remodeled if it's going to be able to turn out the soups and crepes and other dishes that would appeal to residents as well as visitors. Monroe has visions of a hot tub for guests, a sauna maybe, some terraced landscaping on a hillside behind the inn that's overgrown with weeds and vines.

"It's going to be a lot of work," she said. "But it's an opportunity to give it a once over, a facelift. It's going to be fun."

She is taking Smiley's on as a Monroe family project. Her husband, Simon Dunne, an executive with Specialized Bicycles in Morgan Hill, is supportive, but is not directly involved in the deal, now in escrow.


Monroe is no stranger to fixing up old buildings. She lives in a house built in 1883 in San Francisco's Eureka Valley.

"There was a woman who was born, married and died there," she said. "She lived there for 92 years, so the place is mildly haunted in a good way. That's why I love the history that's in these walls. You can tell that there's been a lot of fun had here, a lot of good things have happened here."

For the Monroe family, this isn't their first rodeo when it comes to running a historic business in a small town. For 25 years, her father, Scott Monroe, owned and operated Bailey's Wood Pit Barbecue, the oldest building in Julian, a tiny San Diego County village (pop. 1,502) that is an official California Historical Landmark.

"My parents were hippie surfers," she said, chuckling. "Our family network is surfer restaurateurs. There are lots of us who like the flexible hours and the outdoor lifestyle."

When she was in elementary school, before her parents split up and she went to live with her mother in Hawaii, Leila and other members of her family helped her dad run the bar and restaurant, known for its pulled pork sandwiches, 16 draft beers and live music every Saturday night.

"We were all part of that," she said. "Because of that experience, I grew up working in the service industry whenever I could because I enjoyed it. When I was in law school I was really intrigued by the idea of bringing people together around music and a space. This place goes back to that original concept."


Asked how her reception has been so far in town, she doesn't hesitate, saying, "So far, everyone has been really positive. But who knows what they're saying behind my back. You never know in a small town. But the message I want to give is that I'm really open to suggestions from people who have been coming here and working here for 20 years. Those are the people who have the best ideas about how to make this place even more awesome."

The opportunity to ask those people what they think of Monroe and the inevitable changes she'll bring arose when she left the bar to do some work on a back deck.

Surf instructor Tommy Glavey said he's been surfing with Monroe, and likes that she's what he calls "a water woman."

"From the options that were available, I'm happy to see that she's the one who actually came through," he said as he stood at the bar, talking with friends. "She seems like she's down for the cause."

Wearing a T-shirt with "Bo Gas" on the front, Matt Lundy, a sculptor who runs the town's only gas station, was even more enthusiastic about the change in ownership.

"I know Don (Deane) is tired and is happy to get out from underneath this place," he said. "Let somebody young have it, and she's young enough. She has a positive attitude. She doesn't have an aggressive motivation. She's not going to come in and bulldoze the place and rebuild it. I don't see any bad vibe to it at all."

Article from Marin Independent Journal