• HEAD WEST Marketplace

    HEAD WEST Marketplace
    B Street between 1st and 3rd Aves

    Visit Downtown San Mateo’s B Street for HEAD WEST Marketplace on the third Saturday of every month in 2026! Browse unique gifts or find a treat for yourself from local […]

  • Back to School Bash (with SF Bay Area Moms)

    B Street between 1st and 2nd avenues B Street between 1st and 2nd avenues, San mateo, CA, United States

    Join us for a edu-taining bash on B Street in Downtown San Mateo! Try your hands at arts & crafts, skill games, STEM/sensory play, and activities for all ages. Pick […]

  • Jazz on B Street with Melodic Outreach Endeavor

    B Street between 1st and 2nd avenues B Street between 1st and 2nd avenues, San mateo, CA, United States

    Downtown San Mateo Association presents: Jazz on B Street featuring Melodic Outreach Endeavor Date: Saturday, July 25 Time: 1:00 PM - 3:00 PM Location: B Street (between 1st and 2nd […]

  • The Downtown Express (Free Kids’ train rides)

    Draeger's 222 E 4th Ave, San Mateo, CA, United States

    Date: Sunday, August 2nd Time: 1:00 - 3:00 PM Location: 222 E 4th Ave (former Draeger's Parking Lot) in Downtown San Mateo The Downtown Express! Bringing smiles to Downtown San […]

  • HEAD WEST Marketplace

    HEAD WEST Marketplace
    B Street between 1st and 3rd Aves

    Visit Downtown San Mateo’s B Street for HEAD WEST Marketplace on the third Saturday of every month in 2026! Browse unique gifts or find a treat for yourself from local […]

  • Paw-fect Match adoption pop up

    B Street between 1st and 2nd avenues B Street between 1st and 2nd avenues, San mateo, CA, United States

    Date: Sunday, August 23rd Time: 1:00 - 3:00 PM Location: B Street (near 1st Ave) Find Your Paw-fect Match! 🐾 Looking to add a furry (or feathered!) friend to your […]