• 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 2025
    South B Street South B Street (Between Baldwin Ave. & 2nd Ave.), San Mateo, CA, United States

    Visit Downtown San Mateo's B Street for HEAD WEST Marketplace on the third Sunday of every month in 2025! Browse unique gifts or find a treat for yourself from 50 […]

  • DSMA Board Meeting (Open to the Public)

    DSMA Board Meeting (Open to the Public)
    Chill Spot Rendezvous 271 Baldwin Ave., San Mateo, CA, United States

    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 2025
    South B Street South B Street (Between Baldwin Ave. & 2nd Ave.), San Mateo, CA, United States

    Visit Downtown San Mateo's B Street for HEAD WEST Marketplace on the third Sunday of every month in 2025! Browse unique gifts or find a treat for yourself from 50 […]

  • Summer Splash (with SF Bay Area Moms & Downtown San Mateo Association)

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

    Join us for a Summer Splashin' good time in the pedestrian streets of Downtown San Mateo! Kick off the summer season with arts & crafts, games, STEM/sensory play, and activities for all ages. Pick up a good bag full of summer goodies and connect with mom-approved local businesses! This event is free with complimentary parking […]

  • HEAD WEST Marketplace

    HEAD WEST Marketplace 2025
    South B Street South B Street (Between Baldwin Ave. & 2nd Ave.), San Mateo, CA, United States

    Visit Downtown San Mateo's B Street for HEAD WEST Marketplace on the third Sunday of every month in 2025! Browse unique gifts or find a treat for yourself from 50 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 […]

  • All Aboard! The Downtown Express

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

    Downtown San Mateo Association & Florian Orthodontics present: The Downtown Express Date: August 3rd Time: 12:00 - 2:00 PM Location: 222 E 4th Ave (Farmer's Market at the former Draegers Parking […]

  • Pop Up performance on North B Street: Reyna y su Trio

    North B Street North B Street & Tilton Avenue, San Mateo, CA, United States

    Date: August 16th Time: 5:00 - 6:30 PM Location: Starting at 100 South B Street (in front of Orange Theory), Reyna y su Trio will make multiple stops as they […]