• 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 up a goodie bag with back-to-school goodies and connect with mom-approved local businesses! NOTE CORRECTED TIME is 10am to 12pm!  This event is free with […]

  • 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 Mateo with FREE train rides, face painting from Core Taekwondo, and Clawesome claw machine fun on Sunday, August 2 from 1-3pm! Thanks to our supporters […]

  • 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 […]

  • 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 […]