• DSMA Board Meeting (Open to the Public)

    DSMA Board Meeting (Open to the Public)

    The Downtown San Mateo Association Board and staff, representatives from the City of San Mateo, DSMA members, and other community members gather each month to discuss DSMA business. If you have questions or to confirm the meeting location, please email us at HQ@dsma.org. If you would like to make a presentation to the DSMA Board, […]

  • 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 Makers, Merchants, Crafters, Designers, and Artists. While you’re here, explore Downtown’s retail offerings, and enjoy delicious food from our local spots—there’s something for everyone! More […]

  • 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! This event is free with street parking nearby. Swing by, rock out, […]

  • 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 Avenues) in Downtown San Mateo Don't miss the next Jazz on B Street! Join us on Saturday, July 25, from 1-3pm as Melodic Outreach Endeavor, […]

  • Save the Date! 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 & Clawesome claw machine fun on Sunday, August 2 from 1-3pm! See you there! *Event details may change due to […]

  • DSMA Board Meeting (Open to the Public)

    DSMA Board Meeting (Open to the Public)

    The Downtown San Mateo Association Board and staff, representatives from the City of San Mateo, DSMA members, and other community members gather each month to discuss DSMA business. If you have questions or to confirm the meeting location, please email us at HQ@dsma.org. If you would like to make a presentation to the DSMA Board, […]

  • 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 Makers, Merchants, Crafters, Designers, and Artists. While you’re here, explore Downtown’s retail offerings, and enjoy delicious food from our local spots—there’s something for everyone! More […]

  • 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 […]