3 free holiday listings for 2026: tree lightings, Santa, lights and library holiday crafts. Each one links to the organizer’s own page. We add more as cities and libraries publish their December calendars.
Dec 5
San Mateo Caltrain Station · 385 First Ave, San Mateo, CA 94401
Caltrain's decorated Holiday Train stops in San Mateo, with station performances and balloon artists for families who come to watch.
Good to know: Riding the Holiday Train needs a ticket; the station festivities are open to everyone.
Source: Caltrain · checked Oct 26
DirectionsThese happen every year. We’ll add the 2026 dates as soon as the organizer posts them.
2026 dates not announced yet
Central Recreation Center & Central Park · 50 E 5th Ave, San Mateo, CA 94401
The City of San Mateo's free winter evening with holiday music, crafts, cookie decorating and photo spots for the whole family.
Last year: 2026 not announced yet. 2025: Sat Dec 6, 5–7 pm.
Source: City of San Mateo · checked Oct 26
Directions2026 dates not announced yet
25th Avenue between Hacienda & Flores Streets · 25th Ave between Hacienda St & Flores St, San Mateo, CA 94403
A festive evening stroll on 25th Avenue with lights, music and family fun along the neighborhood's local shops.
Good to know: Free and open to the public; shopping is extra.
Last year: 2026 not announced yet. 2025: Fri Dec 5, 5–8 pm.
Source: San Mateo Area Chamber of Commerce · checked Oct 26
Directions