Downtown San Mateo is ready to get festive

“When I started two years ago, it was pretty quiet in December, so we’ve really ramped up in the last couple years,” Mackenzie Jakoubek, executive director of the Downtown San Mateo Association, said.

While some of the downtown traditions remain, there are also some new specials and offerings this year as well.

Head West

The pop-up-style marketplace is held in different cities throughout the Bay Area, including San Mateo, and features independent small business owners, including local artists, merchants and designers. The holiday event will be Sunday, Dec. 21, from 11 a.m.-4 p.m. on South B Street. Not only can visitors shop for locally made and sourced gifts, but they can enjoy live music and even chat with Santa for the first time.

“We’re partnering with Izzo Therapy to have our first Santa on the pedestrian mall,” Jakoubek said. “Santa will walk through, give kids high-fives and pose for selfies.”

Santa Mateo

This annual event, which supports National Alliance on Mental Illness and local charities, involves 200 Santas participating in a scavenger hunt and fun challenges throughout local venues in downtown San Mateo, taking place on Dec. 6 between 5-10 p.m. Interested residents can head to santamateo.com for more details. 

Breakfast with Santa

Starting at 9 a.m. Dec. 13, Fire Station 21 will host Breakfast with Santa, and children can take photos with Santa on the historic 1921 Fire Engine. Toy donations will also be accepted at the fire station.

San Mateo on Ice

Holidays in San Mateo aren’t complete without San Mateo on Ice, the ice rink situated in Central Park each holiday season. Visitors can enjoy a free skate day Dec. 16 or compete in an ugly sweater competition Dec. 19. On Dec. 11, between 6:45- 8 p.m., residents can watch ice skaters perform during the annual Gala D’Oro, an Italian-themed event inspired by the upcoming 2026 Winter Olympics in Milan. 

Winter Wonderland

Those who aren’t interested in the winter cold can enjoy an indoor wonderland 5-7 p.m. Dec. 6, at the Central Park Recreation Center, where families can listen to music, decorate cookies and do some arts and crafts.

Sounds of the Season

The a cappella band Business Casual will perform a variety of holiday hits on B Street Dec. 6 between 5-6 p.m. You may also catch some of the Santas from the Santa Mateo, as the two events overlap.

Las Posadas

The San Mateo Public Library will celebrate Las Posadas Dec. 17 between 5:30-7 p.m. and Dec. 23 between noon and 2 p.m. The event will include music, food, a live nativity performance and candlelight procession. A performance from Mariachi San Carlos will take place Dec. 17.

Holiday train

Residents can also enjoy live entertainment at the San Mateo train station before boarding Caltrain’s Holiday Train on Dec. 13, take holiday wreath making workshops or shop around at local businesses, many of which are offering gift cards, discounts and specials for holiday shoppers.

Even without an active event taking place, Jakoubek said the area will be festive throughout the entire month.

“This is our second year where we’re having a holiday decorating contest for the businesses, so that’s really fun,” she said. “It definitely feels like the activity level has been increasing every year.”

An extensive list of holiday events can be found at https://dsma.org/events.