• 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 […]

  • 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 […]

  • Boos and Brews on B Street & Trick or Treating

    Downtown San Mateo

    Join us on Saturday, October 24 from 3:00-5:00pm in Downtown San Mateo on B Street & beyond for Boos and Brews on B! Trick-or-treating* Kids Activities Reptile Petting Zoo Arts […]