• Sounds of the Season with Melodic Outreach Endeavor

    Downtown San Mateo

    Celebrate Small Business Saturday in Downtown San Mateo! Visit B Street and beyond on November 29th and enjoy live "Sounds of the Season" music from 12 - 4:30 PM, featuring […]

  • HEAD WEST Marketplace SPECIAL DATE!

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

    SPECIAL DATE! Shop Small in Downtown San Mateo with HEAD WEST Marketplace. Visit Downtown San Mateo's B Street for HEAD WEST Marketplace on the third Sunday of every month in […]

  • Sounds of the Season: Business Casual

    Downtown San Mateo

    Don't miss the unique holiday sounds of Business Casual, the national champion a cappella vocal band known for their smart and surprising genre-swapped covers. Catch their performance on B Street on December 6th from 5-6 PM. The performance is part of a festive evening downtown, coinciding with Santa Mateo, a fun community event where 200 […]

  • HEAD WEST Marketplace – CANCELED DUE TO RAIN

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

    Sorry! The final HEAD WEST San Mateo event for 2025 has been canceled due to the weather. Keep an eye out for 2026 dates! About HEAD WEST: HEAD WEST provides a marketplace for emerging + established local brands and small businesses to have physical selling space multiple times per month at various neighborhood venues. From […]

  • Santa Visit in Downtown San Mateo

    A little rain can’t keep Santa away! We’ve updated the plan for Sunday, December 21st to be indoors! Sunday, Dec 21 at 3 Bees Coffee (224 E 3rd Ave) 12 - 3:30 pm Write a letter (or draw a picture) for Santa with Izzo Therapy 1:30 - 3:30 pm FREE balloon animals at Lions Den […]

  • 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, […]

  • Lunar New Year in Downtown San Mateo

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

    Celebrate Lunar New Year on Saturday, January 24th in Downtown San Mateo! Stay tuned for more information! Brought to you by the DSMA and Florian Orthodontics. This family-friendly event on B Street (between 1st and 2nd Ave) will showcase a Lion Dance performance from Lion Dance Me at noon, plus community booths with activities, red […]

  • San Mateo Sports Warm Up

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

    Kick off your SUPER weekend at our San Mateo Sports Warm Up on Saturday, February 7th from 1–3 pm! We’re bringing the big-game energy to the heart of Downtown with a free, family-friendly afternoon of play featuring a very special appearance by the back-to-back State Champion CSM Bulldogs! Come meet and greet some players from […]