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Members of the May Day Parade kindercourt ride in a Woodside Fire Protection District engine on May 3, 2025. Photo by Magali Gauthier.

The morning of the 103rd May Day Festival started out with gray and cloudy skies but the joy of the annual celebration brought out the sun by noon on Saturday, May 3. Hundreds of people were ready to “giddyup” as they gathered alongside Woodside Road to collect candy and watch neighbors ride on horses and parade floats. 

This year’s May Day theme was “Giddyup, Woodside!” and featured Woodside’s Mounted Patrol, Woodside Elementary School’s class of 1970, Woodside High School marching band, town representatives, WHOA!, Los Trancos Woods Community Marching Band and the eighth grade cast of Woodside Elementary’s operetta “Moana Jr.”

Woodside Elementary School third graders perform the annual maypole dance during Woodside’s May Day celebration on May 3, 2025. Photo by Magali Gauthier.

Kids with paper bags, boxes and umbrellas went crazy as parade participants tossed handfuls of candy as they passed by the crowd. Children were trying to collect as much candy as they could to win the candy grab contest at the end of the parade. The winning prize: bragging rights and candy.

Parade emcees Tyler MacNiven and Melanie Westervelt kept spirits high as they announced each participant with enthusiasm, wit and commentary. 

This year the Woodside PTA honored Karen Seiko Arimoto-Peterson with the title of grand marshal and Sharon LaCrosse Ryan as deputy marshal. 

“Karen has been a lifelong friend of all of ours, of Woodside, of the community,” said MacNiven as the grand marshal rode by on a BMV convertible. “She is the heartbeat.” Arimoto-Peterson graduated from Woodside High School in 1964 and was a teacher at Woodside Elementary for 40 years. She has a deep-rooted connection to the town and dedicates much of her time to various committees and community efforts. 

Ryan has served as the elementary school’s librarian for 25 years and is well known among the students of Woodside. She was recognized for her dedication to organizing student service projects, maintaining the school’s library and organizing events and programs for students. 

“Now we have nepotism at its finest. It’s the Kindercourt riding in on the old white fire engine,” yelled MacNiven. The young royalty of this year’s kindergarten court, dressed in capes and crowns, waved to the crowd throwing candy and demonstrating the noble attributes of sharing and caring.

Woodside Fire Protection District trucks and engines make their way through the May Day Parade in Woodside on May 3, 2025. Photo by Magali Gauthier.

This year’s court honored King Tyson Boitnott and Queen Sasha Lazaro, Princesses Valentina Arguello and Kelsie Simkover and Princes Andres Guerrero and Silas Hall. 

The past and the present joined together as the following float featured Woodside Elementary’s Class of 1970. Many alumni traveled from across the country to reunite and celebrate May Day on a 1935 fire engine.

The parade briefly came to a stop as the eighth grade operetta cast gave a special preview of their 2025 performance, “Moana Jr.” Students hopped off a float resembling the Disney princess Moan’s seacraft as they took stage on Woodside Road. The cast performed a musical number as the student playing Maui sang “You’re Welcome,” to the crowd. 

After the parade, the community gathered at the Woodside School Amphitheater for the award ceremony and may pole dance. 

“The Woodside parade is more than just a procession and the may pole dance is more than a charming tradition,” said Mayor Brian Dombkowski. “These are both living testaments to our shared history and the values that unite us together for over 100 years. These traditions remind us of our roots.”

Dombkowski also recognized the town’s incoming Town Manager Jason Ledbetter, who will be taking over from current Town Manager Kevin Bryant on May 15. 

Following speeches and the honoring of the grand and deputy marshals, the honoree of the Elward Thomas Citizen of the Year Award was announced. This year, the award was given to Jenny Hayden, Woodside Elementary school board president.

Rachel Ream, right, hugs Citizen of Year Award recipient Jenny Hayden, left, during the May Day celebration at Woodside Elementary School on May 3, 2025. Photo by Magali Gauthier.

Hayden, who has been a lifelong resident of Woodside, has been serving the school board since 2018. She was honored for the many hours she’s devoted to school events. Hayden also was recognized for the efforts she made to campaign for two ballot measure campaigns, Measure E and Y, to ensure the school secured critical funding. 

To finish out the ceremony, the Woodside Elementary third graders adorned with flower crowns and pastel outfits, walked through the amphitheater as they took the stage for the anticipated maypole dance. The dancers decorated the pole with long strings of colorful ribbon in a well executed performance that was met with smiles and applause from the audience. 

The May Day festivities continued into the afternoon as community members went up to the school yard to enjoy a barbecue lunch, carnival games and quality time. 

Members of the Mounted Patrol of San Mateo County lead the May Day Parade in Woodside on May 3, 2025. Photo by Magali Gauthier.

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Jennifer Yoshikoshi joined The Almanac in 2024 as an education, Woodside and Portola Valley reporter. Jennifer started her journalism career in college radio and podcasting at UC Santa Barbara, where she...

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