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Judge Wolcott plays the banjo with friends at the May Day Music and Arts Festival, held at Pie Ranch in Pescadero, on May 3, 2025. Photo by Anna Hoch-Kenney.

Pescadero’s quaint and quiet Pie Ranch has become a regular pit stop for many day-trippers driving along scenic Highway 1, but those who popped by the ranch’s roadside farm stand last weekend found themselves walking into a scene that could have been straight out of the ‘70s.

From May 3-4, Pie Ranch opened its gates to an estimated 650 festivalgoers for the fourth annual May Day Music and Art Festival, organized by Boulder Creek-based nonprofit Lille Aeske Art House. Tents and tailgate jam sessions sprung up as camper vans piled onto the property. Festivalgoers in tie-dye overalls, fur coats and long flowing dresses skipped arm in arm along a dirt road connecting the two stages as the winds picked up folk, bluegrass and roots music from the festival’s two stages.

A group of unsuspecting visitors looking to buy pie and other goodies at the farm stand was pleasantly surprised to stumble upon Aviva LeFay performing her barely accompanied, hypnotic melodies to a swaying crowd at the festival’s intimate “barn stage”, set up just past the farm stand. 

“They ran out of pie, but it was still worth the stop!” one of the group members declared triumphantly as they climbed back in their car at the end of the set.

While this was the festival’s fourth year, it was a groundbreaking one for organizers. This was the first year that the festival went for two days, the first time it offered camping and the first year it was held at Pie Ranch — the latter being a key component to the event’s expansion in 2025.

Founded in 2002, Pie Ranch is no stranger to musical performances: It has a long-standing tradition of hosting a monthly barn dance (or meadow dance, depending on the time of year). Featuring live folk music and a dance caller, the dances draw people from throughout the Bay Area and beyond.

This year’s May Day music lineup largely reflected the Bay Area roots and folk music scene, with touches of alt-rock and psychedelic jam-band sounds. Many of the musicians were local to the larger Bay Area, but some came from as far as the Midwest.

Vanessa May of the Rainbow Girls performs at the May Day Music and Arts Festival. Photo by Anna Hoch-Kenney.

Anil Prajapati, managing director of Lille Aeske Art House and one of the main organizers of the festival, explained that it actually started as a virtual event to help connect people to local music during the pandemic. When COVID restrictions eased the following year, organizers made the virtual concert series into a one-day festival, hosted at Felton’s Hallcrest Vineyards. 

The festivals started to garner a local following. By 2025, organizers were looking to expand the event into a “full festival experience” that could go into the night and allow for overnight camping — enter Pie Ranch. 

A camper truck passes a group of festivalgoers on the road between the two stages at the May Day Music and Arts Festival. Burn scars from the CZU Fire can still be seen on the ridge behind the ranch. Photo by Anna Hoch-Kenney.

“We gave them our vision and what we wanted. It felt like a good fit and they were excited to have it,” Prajapati said, adding that the Pie Ranch staff and owners joined throughout the day to listen to music and soak up the festivities. “It’s been really nice…and we’re hoping this will be a continued collaboration,” he said.

The Pie Ranch setting left a lasting impression on festivalgoers as well. 

“I got here and I actually started tearing up because of how beautiful it was,” said Maddie O’Mahony, a festival attendee and first-time Pie Ranch visitor as she looked out over the green hillside at the main stage from a vendor tent, where she was getting a henna tattoo. 

Clockwise from left, Bill Murray, Bill Wolcott, Judge Wolcott, Laird Henkel and Kriss Neuman pull out their instruments for a jam session at their campsite between sets at the at the May Day Music and Arts Festival. Photo by Anna Hoch-Kenney.

May Day theme

The festival’s name is a nod to more than just the timing of the event. When it came to finding vendors, Lille Aeske Art House turned to other nonprofits and organizations that specifically focused on uplifting industry underdogs to help fill needs.

For example, wine and beer was served by The Vinguard, an organization that focuses on supporting marginalized groups within the natural wine industry, with a special focus on women, vineyard workers and members of the LGBTQ community. Louie Seamus, founder of The Vinguard, said that all the wines the organization served during the festival were made by women. 

“There’s this overlap of what our values are…and it’s so important to have that here. That is what creates community,” Seamus said of their first experience bringing The Vinguard to the festival.

Aerialist Sierra Camille performs above the audience at the May Day Music and Arts Festival. Photo by Anna Hoch-Kenney.

Cheyanne Donald-Diaz, founder of White Rabbit Social Club, helped bring additional local vendors to the event. 

“My whole business model is based around creating a safe space for up-and-coming artists and small businesses so that they can learn how to kind of get their business from being a hobby to a full-fledged space,” Donald-Diaz said. “I make sure that most of my events have at least 10 brand new vendors in them that I haven’t worked with before, or vendors that have never worked in the industry before and are trying to just make their business happen.”

This year’s vendor lineup included jewelry makers, vintage boutiques, ceramicists, homemade arts and crafts businesses, a massage therapist, a henna artist and a variety of food vendors.

Maddie O’Mahony, left, gets a henna tattoo from Silvana Piga at the May Day Music and Arts Festival. Photo by Anna Hoch-Kenney.

Donald-Diaz, whose organization has been helping to creatively fill vendor slots since the first in-person May Day music event, said that the festival can make a huge difference for an up-and-coming artist. 

“I think that one of the biggest things for artists and any vendor is getting themselves in front of the right crowd, getting themselves in front of people who want to support them and understanding how what they do works within a public setting,” she said. “And so being able to participate in these festivals gives them that opportunity to really push themselves forward and make something new.”

Many of the performing artists alluded to the importance of social justice, talking candidly with audiences about topics like their support for Gaza and the importance of sexual consent — though perhaps none tied quite as closely to the May Day concept as the Rainbow Girls crooning the lyrics to their heartbreakingly relatable song “American Dream.”

“Everyone’s worth something, and it’s not their weight in gold,” the trio repeated as aerial artist Sierra Camille, wearing a gold body leotard, slowly twirled on silks above the enthralled audience.

Raja Bandit, left, dances with 3-year-old Piper at the May Day Music and Arts Festival. Photo by Anna Hoch-Kenney.

Reflecting and looking ahead

This year’s May Day fest posed no shortage of challenges for organizers. On top of the regular challenges of putting together a large-scale event, organizers dealt with increasing event expenses, limited infrastructure due to the remote setting of this year’s festival and rain and coastal storm warnings on the first day of the event. Nevertheless, the festival seemed to go off without a hitch.

Prajapati said that organizers focused on preparedness to help address some of the challenges. They brought in backup generators along with medical and security teams to ensure they could immediately address any issues in case it took outside teams too long to arrive, and they had a crew on-site that made sure everything was set up, covered and protected. Despite rain and strong winds on Saturday morning, everything crucial survived unscathed.

A crowd listens to the Rainbow Girls perform at the fourth annual May Day Music and Arts Festival. Photo by Anna Hoch-Kenney.

While increasing rental and insurance prices still pose a threat to the future of the event, Prajapati said the team got creative with their solutions when they could, opting to buy certain equipment as opposed to renting. 

“If you’re not careful doing an event like this, you can spend way more than you can even imagine…But if you do it right, you can hit the even deal and make it good,” Prajapati said.

Prajapati and the organizing team hope to bring the event back to Pie Ranch next year and say that the community can help make it happen by donating to the Lille Aeske Art House nonprofit.

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Anna Hoch-Kenney joined Embarcadero Media as the staff visual journalist and assistant audience engagement editor in April of 2024. Anna started her photojournalism career at the City College of San Francisco....

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