Pleasure Point Street Fair

Local businesses and artisans attract large crowds at the 10th annual Pleasure Point Street Fair

By Neal Kearney
June 26, 2024

Last Saturday afternoon, I rode my bike down Portola Drive, en route to the 10th annual Pleasure Point Street Fair. As the warm June sun warmed my skin and colored my mood, I cleared my throat a few times to prepare my vocals for the endless chit-chat that was bound to ensue. As I locked my bike to a fence where the old Big Creek lumberyard used to stand, I could hear the crowd thrumming with excitement as groovy surf music rang out in the background. 

When I lifted my head, I took in an incredibly busy scene—couples strolling with arms locked, sun-kissed moms pushing strollers, pack of excited young kids. The place was packed! Despite this, as I entered the sea of people I slowly realized that I couldn’t identify one person I knew. I told myself that this would surely change as I made it deeper into the fold of the popular street fair, where local artisans and business owners have been showcasing and selling their wares to great results for the past decade. 

The fine folks at Toasted Jewelry

However, as I reached the halfway point of the sprawling outdoor marketplace I had yet to bump into anyone familiar. I marveled at my anonymity at such a large gathering merely walking distance from my house. Not wanting the effort of all that throat clearing to have been in vain, I decided to inspect the booth that lined the wide drive, whose asphalt was beginning to shimmer from the mid-day sun’s toasty Early Summer beams. Finally, success! I’d found a homie!

I veered over to one of the many pop-up tents and was greeted by the lovely smile of local artist Maia Negre. She was clearly in the middle of selling a painting, so I just lifted my hand in greeting and smiled back. I spent another few moments admiring her unbelievably sublime paintings, then peeled off to do a hot lap through the beer garden.

Anastasiya Bachmnova, from Follow The Sun Art, was there too!!

Now, I don’t partake in the naughty bubbles, personally, but wanted to get a quote from a longtime Point resident and figured the 21-and-up portion was just as good a place as any to find a festive friend to coerce some wise words out of. I traced the horseshoe perimeter, stopping briefly at the stage to slide through a handful of my legendary dance moves along the way, surely impressing all in attendance. That righteous boogie carried me all the way back to the place that I’d started. Still, not one person I knew. That all changed when I approached the exit, and saw a a few of my pals deep in discussion.

Never one to miss the opportunity to hear the sound of my own voice, I stepped in between them, forcing my way into their private pow-wow. After exchanging pleasantries, the subject centered around how odd it felt being around so many strangers, and the inevitable comparisons to the Point we’d grown up in started up in earnest. Always one to look on the bright side, Pleasure Point ripper Trevor Thorpe weighed in.

“Man, there’s a lot of new faces,” he admitted. “That’s the new normal. There’s no getting around the fact that there’s all these new faces in town. They’re here to stay, so it’s great that we’re all down here, getting to know each other and having a good time. We’re not gonna go back to the past, so let’s try to make this work going forward so we can focus on having fun”.

Jackie and Martijn from Ventana Surfboards

“Amen,” I said, offering my fist to bump in solidarity.

After some more jawing, I bid my friends farewell and continued onwards through the packed scene. As I moseyed down the road, I was lured deeper by the live, dreamlike tunes of the world famous Mermen. I observed tons of local businesses crushing it, satisfying long time customers while introducing their brands to tons of new clientele. Outfits such as Blue Zone Waters, Golden Pet Life, Ola Chica, and Wetfoot Photography. Even the perpetually smiling Anastasiya Bachmanova was in the mixture, selling her ocean-centric gift cards and prints like hot cakes.



By the time I reached the end, it dawned on me that I had, in fact, seen plenty of friends along the way, just not all my friends, as would have been the case at a gathering like this on Pleasure Point in days passed. I was actually relieved. Sometimes it’s nice to spend time somewhere you frequent without having to trade tired pleasantries with every last person in attendance.

Olivia and Alayna with Blue Zone Waters

As that thought came and went, my dependable desire to hear the sound of my own voice propelled me forward, straight into the booth of local artist Jimbo Phillips, who was holding court inside one of his colorful and eye-catching tents. After reading the room, I respectfully waited for Phillips to seal a deal with a prospective customer. As soon as that overstuffed cash register clicked, I set upon him for a quote.



Once cornered, I asked him about the logo he designed for this year’s event, just as he had for every year of the popular street fair’s existence.

“There’s a new logo every year,” he told me. “Usually based on a theme. I put the otter in there, due to all the Otter 841 vibes we’ve been having lately (laughs). I wanted to get her in there, a wave, the sun, and of course, a surfer. This year I tried to keep in summery and fun.”


Master money manipulator, Jimbo Phillips

He too, agreed that the event was a good opportunity for longtime Point locals and new faces alike to mix and mingle.

“It brings the community together, you know? Everyone comes out to meet up from the different neighborhoods around town, as well as people visiting from surrounding areas. It’s a cool community event where you can run into people you haven’t seen for years and also meet someone for the first time. It’s important to have local events like this so we’re able to do that more often. It’s a fun tradition, and hopefully we can keep it going.”

When the crowds began to subside and vendors began the long process of packing up for the day, I walked back to my bike, injected with optimism, even in the face of my Hawaiian shaved-ice melting into a sugary syrup. Till next year!

Rocking out with the world famous Mermen

-all photos by @split_peak_soup