Head West Marketplace — South B Street III

HEAD WEST Marketplace is set to take over South B Street in downtown San Mateo on Saturday, May 16, for a one-day outdoor market featuring local makers, artists, designers and vintage merchants. The event is scheduled for 11 a.m. to 5 p.m. on B Street between 1st and 3rd avenues, according to HEAD WEST’s event page and Downtown San Mateo’s calendar. HEAD WEST describes itself as a Bay Area outdoor marketplace that runs on weekends from March through December at multiple venues. Festival Guides and Reviews also lists the San Mateo stop on its 2026 California festival calendar. ### Where exactly is the San Mateo market taking place? South B Street between 1st Avenue and 3rd Avenue is the listed footprint for the May 16 market in San Mateo. HEAD WEST’s South B Street page gives the address as San Mateo, California 94401 and says the downtown district includes a concentrated retail and restaurant corridor. Downtown San Mateo’s event listing uses the same B Street between 1st and 3rd avenues location. (headwestmarketplace.com) Downtown San Mateo identifies the event area as part of its central shopping and dining district. That places the market in a pedestrian-heavy stretch where shoppers can move between vendor booths and nearby storefronts during the event window, according to the downtown organization’s calendar description. ### When does it start, and is this a one-off event? Saturday, May 16, is the next scheduled San Mateo date, and the published hours are 11 a.m. to 5 p.m. (headwestmarketplace.com) HEAD WEST’s event page labels May 16 as the “next up” date for South B Street, while Downtown San Mateo lists the same start and end times on its 2026 events calendar. The third Saturday of every month in 2026 is how Downtown San Mateo describes the San Mateo run of HEAD WEST Marketplace. (dsma.org) The downtown calendar lists follow-on dates including June 20, July 18, Aug. 15, Sept. 19 and Oct. 17, with shorter 11 a.m. to 4 p.m. hours posted for November and December. ### What kind of vendors are expected on South B Street? HEAD WEST says its markets bring together makers, crafters, artists, designers, vintage merchants and live music. (headwestmarketplace.com) Downtown San Mateo’s description of the San Mateo series uses similar language, saying shoppers can browse goods from local makers, merchants, crafters, designers and artists. Festival Guides and Reviews lists the May 16 stop as “Head West Marketplace: South B Street III” in its statewide calendar. (dsma.org) That listing does not add operating details beyond the date and city, but it aligns with the HEAD WEST and Downtown San Mateo postings that identify the event as part of the recurring San Mateo schedule. ### Is there an admission charge or ticket requirement? (headwestmarketplace.com) DoTheBay lists the May 16 San Mateo event and provides an event page, but the primary organizer pages from HEAD WEST and Downtown San Mateo do not describe the market as ticketed. A Bandsintown listing for musician Gaby Castro’s appearance at the market says the May 16 event has free admission, though that detail appears on a third-party page rather than the organizer’s main event notice. (festivalguidesandreviews.com) HEAD WEST’s own site presents the San Mateo stop as part of its regular public marketplace schedule. The organizer also says the broader marketplace series runs every weekend from March to December across Bay Area venues. ### Where can shoppers check vendors or future dates? HEAD WEST directs visitors to its South B Street page and broader dates-and-venues calendar for current scheduling. (dothebay.com) Downtown San Mateo also maintains a 2026 HEAD WEST Marketplace page that lists the monthly South B Street dates and the event location. Festival Guides and Reviews includes the May 16 San Mateo listing in its California festival roundup. (headwestmarketplace.com) June 20 is the next posted San Mateo date after the May 16 market, according to Downtown San Mateo’s events calendar. HEAD WEST’s San Mateo page remains the organizer’s main reference point for the South B Street stop as Saturday approaches. (headwestmarketplace.com)