Head West Marketplace — South B Street, San Mateo

Head West Marketplace is scheduled to take over South B Street in downtown San Mateo on Saturday, May 16, with an outdoor market of local makers, artists, merchants and food options, according to Head West and Downtown San Mateo listings. The event is set for 11 a.m. to 5 p.m. along South B Street between 1st and 3rd avenues. Head West describes itself as a Bay Area outdoor marketplace that runs on weekends from March through December at multiple venues. ### Where exactly is the market and when does it run? Saturday, May 16, is the next San Mateo date listed by Head West for its South B Street market. The organizer’s event page says the market will run from 11 a.m. to 5 p.m. in downtown San Mateo, CA 94401. South B Street between 1st Avenue and 3rd Avenue is the location identified by both Head West and Downtown San Mateo. (headwestmarketplace.com) Downtown San Mateo’s event listing describes the site more simply as B Street between 1st and 3rd avenues, while Head West’s own page labels it South B Street. ### What kind of market is Head West putting on in San Mateo? (headwestmarketplace.com) Head West says the San Mateo event features makers, crafters, artists, designers and merchants in an outdoor street-market format. The company’s main site says its markets also include live music across its Bay Area events. Downtown San Mateo’s listing says shoppers can browse gifts and goods from local makers, merchants, crafters, designers and artists. (headwestmarketplace.com) The same listing says visitors can also use the market visit to explore downtown retail stores and nearby food businesses. ### How big is the San Mateo stop expected to be? Head West’s participant FAQ says the South B Street market typically has 25 to 50 booths and estimated foot traffic of 1,000 to 2,000 people. (headwestmarketplace.com) The FAQ describes the venue as two blocks of pedestrian-only street space. The same FAQ says the San Mateo site is a “cart in only” venue for vendors, meaning sellers cannot pull vehicles directly up to booth spaces for setup and breakdown. (dsma.org) Head West says parking is available within one to two short blocks, with a garage accessible nearby. ### Is this a one-off event or part of a series? (headwestmarketplace.com) Downtown San Mateo says Head West Marketplace is scheduled for the third Saturday of every month in 2026. The city-linked event calendar lists May 16, June 20, July 18, Aug. 15, Sept. 19, Oct. 17, Nov. 21 and Dec. 19 for the San Mateo series. Festival Guides and Reviews separately lists “Head West Marketplace: South B Street III” in its May 14-17, 2026 western festival roundup. (headwestmarketplace.com) That naming suggests the May 16 market is the third San Mateo date in the 2026 run, following earlier spring installments. ### What should visitors know before they go? (dsma.org) Head West lists the event as outdoors and free to attend on its public-facing market pages. A separate DoTheBay listing for the same May 16 event also describes admission as free. Downtown San Mateo says the market is intended for browsing local goods and stopping at nearby restaurants and shops in the downtown district. (festivalguidesandreviews.com) Head West’s South B Street page describes downtown San Mateo as a compact retail and dining area spread across five square blocks. ### What comes after the May 16 market? (headwestmarketplace.com) June 20, 2026, is the next San Mateo date listed after the May event on Downtown San Mateo’s calendar. The same calendar lists July 18 as the following market date, with November and December hours shortened to 11 a.m. to 4 p.m. instead of the 11 a.m. to 5 p.m. schedule used from March through October. (dsma.org) (headwestmarketplace.com)