The event is a bit of a throwback to another era. As Woodside Councilman Dick Brown said as he strolled up Woodside Road before the parade on May 4: "This is one of the last May Day events around."
The day begins with a fun run, followed by a pancake breakfast at Village Church. But things don't really get going until the parade begins.
The 97th annual May Day Parade was led by grand marshal Betsy Hobson, who rode in a 1968 Pontiac GTO convertible.
Hobson had the place of honor this year in recognition of her volunteer work in a town that relies heavily on community involvement. She served on the Woodside Elementary School District board for eight years and on the Planning Commission for 16 years, and co-founded the Woodside School Foundation.
Following her lead, a carousel that included a bright red vintage firetruck, lovingly pampered custom and antique cars, and phalanxes of horses and ponies clattered down Woodside Road to the center of town and then turned around and returned to the parade starting line in front of the school.
After a van carrying members of the Town Council came a longtime Woodside Elementary tradition: The members of the Kindergarten Royal Court, known as "the future of Woodside," with King Jaden and Queen Margot, princesses Fiona and Josie and princes Romeo and Reid.
Behind them was the eighth-grade class promoting their production of "The Little Mermaid" that will take place between May 29 and June 1. Next up was the school foundation float, followed by the Los Trancos Woods Community Marching Band and Woodside High Marching Band, stirring everyone's spirits. Village Church musical director Andrew Hall and his jazz band, Hot Baked Goods, entertained the crowd with their Dixieland favorites, including "When the Saints Go Marching In."
Following the parade was the performance by the Kindergarten Royal Court, followed by the May pole dance performed by the third-grade class decked out in yellow and blue attire.
After the performances, Woodside Elementary Principal Steve Frank presented the Citizen of the Year award to Jeanne Connolly, whose fourth child, Charles, will be graduating in June.
Frank praised her for being willing "to put in countless hours serving the school."
Connolly said the family moved to Woodside from Palo Alto in 2003 because she "fell in love with an old house" she found for sale.
She said she didn't realize how much more she would be getting in the move.
"Someone said 'Go down and enroll your kids in public school,'" she said. "I got so much more than I ever expected."
Connolly was on the Woodside School Foundation board for nine years and ran the annual fund campaign. She was also the producer of two eighth-grade operettas along the way.
"The best part is all the people I've gotten to know through volunteering," she said.
"I'm not good at saying no," she added.
After the award ceremony, residents headed to the Woodside Elementary playground, where the afternoon carnival and barbecue were underway.
Heide Poppenberg, a 35-year Woodside resident, said she's always loved the annual tradition.
"I've had five grandchildren go through the school plus my youngest daughter," she said. "What I like best about May Day is that it doesn't change."