BEGIN:VCALENDAR VERSION:2.0 PRODID:-//Downtown San Mateo - ECPv6.16.2//NONSGML v1.0//EN CALSCALE:GREGORIAN METHOD:PUBLISH X-ORIGINAL-URL:https://dsma.org X-WR-CALDESC:Events for Downtown San Mateo REFRESH-INTERVAL;VALUE=DURATION:PT1H X-Robots-Tag:noindex X-PUBLISHED-TTL:PT1H BEGIN:VTIMEZONE TZID:America/Los_Angeles BEGIN:DAYLIGHT TZOFFSETFROM:-0800 TZOFFSETTO:-0700 TZNAME:PDT DTSTART:20240310T100000 END:DAYLIGHT BEGIN:STANDARD TZOFFSETFROM:-0700 TZOFFSETTO:-0800 TZNAME:PST DTSTART:20241103T090000 END:STANDARD BEGIN:DAYLIGHT TZOFFSETFROM:-0800 TZOFFSETTO:-0700 TZNAME:PDT DTSTART:20250309T100000 END:DAYLIGHT BEGIN:STANDARD TZOFFSETFROM:-0700 TZOFFSETTO:-0800 TZNAME:PST DTSTART:20251102T090000 END:STANDARD BEGIN:DAYLIGHT TZOFFSETFROM:-0800 TZOFFSETTO:-0700 TZNAME:PDT DTSTART:20260308T100000 END:DAYLIGHT BEGIN:STANDARD TZOFFSETFROM:-0700 TZOFFSETTO:-0800 TZNAME:PST DTSTART:20261101T090000 END:STANDARD BEGIN:DAYLIGHT TZOFFSETFROM:-0800 TZOFFSETTO:-0700 TZNAME:PDT DTSTART:20270314T100000 END:DAYLIGHT BEGIN:STANDARD TZOFFSETFROM:-0700 TZOFFSETTO:-0800 TZNAME:PST DTSTART:20271107T090000 END:STANDARD END:VTIMEZONE BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20260301T130000 DTEND;TZID=America/Los_Angeles:20260301T150000 DTSTAMP:20260521T184158 CREATED:20260213T174839Z LAST-MODIFIED:20260213T174839Z UID:10003130-1772370000-1772377200@dsma.org SUMMARY:Jazz on B Street with The Birds DESCRIPTION:Join us for Jazz on B Street on Sunday\, March 1st\, as we welcome the Birds to Downtown San Mateo! \nCome out and enjoy a lively afternoon of jazz performed by some of our community’s brightest young musicians. The Birds bring the perfect soundtrack for a Sunday stroll\, lunch date\, or afternoon coffee on B Street. \nJazz on B Street is free and open to the public. Grab a bite from one of Downtown’s amazing restaurants\, support local\, and soak in the sounds of live music in the heart of San Mateo. \n**Event details may change due to inclement weather. \nDate: Sunday\, March 1st\nTime: 1:00 PM – 3:00 PM\nLocation: B Street (between 1st and 2nd Avenues) in Downtown San Mateo URL:https://dsma.org/event/jazz-on-b-street-with-the-birds/ LOCATION:B Street between 1st and 2nd avenues\, B Street between 1st and 2nd avenues\, San mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2026/02/Copy-of-20251004_JazzOnBStreet-square.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20260210T090000 DTEND;TZID=America/Los_Angeles:20260210T100000 DTSTAMP:20260521T184158 CREATED:20250106T174057Z LAST-MODIFIED:20250616T172038Z UID:10001197-1770714000-1770717600@dsma.org SUMMARY:DSMA Board Meeting (Open to the Public) DESCRIPTION: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. \nIf you have questions or to confirm the meeting location\, please email us at HQ@dsma.org. \nIf you would like to make a presentation to the DSMA Board\, reach out by email at least one month before the scheduled meeting. URL:https://dsma.org/event/dsma-board-meeting-open-to-the-public/2026-02-10/ CATEGORIES:Events ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20260207T130000 DTEND;TZID=America/Los_Angeles:20260207T150000 DTSTAMP:20260521T184158 CREATED:20260105T175814Z LAST-MODIFIED:20260115T185145Z UID:10003102-1770469200-1770476400@dsma.org SUMMARY:San Mateo Sports Warm Up DESCRIPTION: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 the College of San Mateo’s elite football team before testing your own skills on the Perform for Golf putting green\, foosball and ping pong tables\, and the San Mateo Parks & Rec mobile games. For those looking for a unique challenge\, don’t miss a live demo from the Belmont Brass Wrists arm wrestling club! \nThis community celebration is made possible through a generous partnership with Perform For Golf\, and it’s the perfect way to soak up the Bay Area’s championship vibes just one day before the Super Bowl. Special thanks to the San Mateo Area Chamber of Commerce\, the City of San Mateo\, the City of San Mateo’s Parks & Rec Dept\, CSM\, and the Belmont Brass Wrists! \n*Event details may change in case of inclement weather. Registration is not required\, but space and supplies are limited. URL:https://dsma.org/event/san-mateo-sports-warm-up/ LOCATION:South B Street\, South B Street (Between Baldwin Ave. & 2nd Ave.)\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2026/01/Green-and-Yellow-Illustrative-National-Sports-Day-Instagram-Post.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20260124T120000 DTEND;TZID=America/Los_Angeles:20260124T140000 DTSTAMP:20260521T184158 CREATED:20251203T180920Z LAST-MODIFIED:20260105T175424Z UID:10003005-1769256000-1769263200@dsma.org SUMMARY:Lunar New Year in Downtown San Mateo DESCRIPTION: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. \nThis 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 envelopes\, and give-aways for kids from noon to 2pm*. \n\nCommunity booths on B Street\nnoon-2pm\nLion Dance ME performance on B Street\nnoon-1pm\nLion Dance ME parade to businesses throughout Downtown\n1-2pm \n\n\n  \n\n*Event details may change in case of inclement weather. Registration is not required\, but space and supplies are limited. URL:https://dsma.org/event/lunar-new-year-in-downtown-san-mateo/ LOCATION:South B Street\, South B Street (Between Baldwin Ave. & 2nd Ave.)\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2025/12/2026-Lunar-New-Year-Sponsor-Deck-Instagram-Post-45-1.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20260113T090000 DTEND;TZID=America/Los_Angeles:20260113T100000 DTSTAMP:20260521T184158 CREATED:20250106T174057Z LAST-MODIFIED:20250616T172038Z UID:10001196-1768294800-1768298400@dsma.org SUMMARY:DSMA Board Meeting (Open to the Public) DESCRIPTION: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. \nIf you have questions or to confirm the meeting location\, please email us at HQ@dsma.org. \nIf you would like to make a presentation to the DSMA Board\, reach out by email at least one month before the scheduled meeting. URL:https://dsma.org/event/dsma-board-meeting-open-to-the-public/2026-01-13/ CATEGORIES:Events ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251221T120000 DTEND;TZID=America/Los_Angeles:20251221T153000 DTSTAMP:20260521T184158 CREATED:20251217T193936Z LAST-MODIFIED:20251218T183834Z UID:10003036-1766318400-1766331000@dsma.org SUMMARY:Santa Visit in Downtown San Mateo DESCRIPTION:A little rain can’t keep Santa away! We’ve updated the plan for Sunday\, December 21st to be indoors! \nSunday\, Dec 21 \nat 3 Bees Coffee (224 E 3rd Ave)\n12 – 3:30 pm Write a letter (or draw a picture) for Santa with Izzo Therapy\n1:30 – 3:30 pm FREE balloon animals \nat Lions Den Shave Parlor (236 E 3rd Ave)\n12 – 3:00 pm Meet Santa! \n*all activities are first come\, first served URL:https://dsma.org/event/santa-visit-in-downtown-san-mateo/ CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2025/12/Copy-of-Santa-Visit-Dec-2025-Instagram-Post-45-scaled.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251221T110000 DTEND;TZID=America/Los_Angeles:20251221T110000 DTSTAMP:20260521T184158 CREATED:20250210T225929Z LAST-MODIFIED:20251217T185350Z UID:10001364-1766314800-1766314800@dsma.org SUMMARY:HEAD WEST Marketplace - CANCELED DUE TO RAIN DESCRIPTION:Sorry! The final HEAD WEST San Mateo event for 2025 has been canceled due to the weather. Keep an eye out for 2026 dates! \nAbout HEAD WEST:\nHEAD 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 hand-made ceramics to locally sourced vintage\, there are always new categories of goods available to explore. Connecting people\, forging community + sustaining the local economy\, we continue to build upon our presence by offering expanded resources for small businesses to learn\, grow\, connect + share. Interested in applying to be a HEAD WEST vendor? Visit HEADWEST.com/apply \nNeed help finding your way to Downtown San Mateo? Visit our DIRECTIONS and PARKING pages \n*Event details may change due to inclement weather. URL:https://dsma.org/event/2025head-west-marketplace-3/ LOCATION:South B Street\, South B Street (Between Baldwin Ave. & 2nd Ave.)\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/png:https://dsma.org/wp-content/uploads/2025/02/South-B-Street-1080x1080-copy.png ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251209T090000 DTEND;TZID=America/Los_Angeles:20251209T100000 DTSTAMP:20260521T184158 CREATED:20250106T174057Z LAST-MODIFIED:20250616T172038Z UID:10001195-1765270800-1765274400@dsma.org SUMMARY:DSMA Board Meeting (Open to the Public) DESCRIPTION: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. \nIf you have questions or to confirm the meeting location\, please email us at HQ@dsma.org. \nIf you would like to make a presentation to the DSMA Board\, reach out by email at least one month before the scheduled meeting. URL:https://dsma.org/event/dsma-board-meeting-open-to-the-public/2025-12-09/ CATEGORIES:Events ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251206T170000 DTEND;TZID=America/Los_Angeles:20251206T180000 DTSTAMP:20260521T184158 CREATED:20251120T194946Z LAST-MODIFIED:20251120T194946Z UID:10002939-1765040400-1765044000@dsma.org SUMMARY:Sounds of the Season: Business Casual DESCRIPTION: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. \nThe performance is part of a festive evening downtown\, coinciding with Santa Mateo\, a fun community event where 200 Santas will be running through the area! URL:https://dsma.org/event/sounds-of-the-season-business-casual-2/ LOCATION:Downtown San Mateo CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2025/11/HWM_SouthBStreet_120824_019-e1763668156486.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251130T110000 DTEND;TZID=America/Los_Angeles:20251130T160000 DTSTAMP:20260521T184158 CREATED:20250210T225854Z LAST-MODIFIED:20251125T164815Z UID:10001363-1764500400-1764518400@dsma.org SUMMARY:HEAD WEST Marketplace SPECIAL DATE! DESCRIPTION:SPECIAL DATE! Shop Small in Downtown San Mateo with HEAD WEST Marketplace. \nVisit 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 this season! \nMore about HEAD WEST: \n\n\nHEAD 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 hand-made ceramics to locally sourced vintage\, there are always new categories of goods available to explore. Connecting people\, forging community + sustaining the local economy\, we continue to build upon our presence by offering expanded resources for small businesses to learn\, grow\, connect + share. Interested in applying to be a HEAD WEST vendor? Visit HEADWEST.com/apply \nNeed help finding your way to Downtown San Mateo? Visit our DIRECTIONS and PARKING pages \n*Event details may change due to inclement weather. URL:https://dsma.org/event/2025head-west-marketplace-2/ LOCATION:South B Street\, South B Street (Between Baldwin Ave. & 2nd Ave.)\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/png:https://dsma.org/wp-content/uploads/2025/02/South-B-Street-1080x1080-copy.png ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251129T120000 DTEND;TZID=America/Los_Angeles:20251129T163000 DTSTAMP:20260521T184158 CREATED:20251120T004708Z LAST-MODIFIED:20251120T004708Z UID:10002937-1764417600-1764433800@dsma.org SUMMARY:Sounds of the Season with Melodic Outreach Endeavor DESCRIPTION:Celebrate Small Business Saturday in Downtown San Mateo! \nVisit B Street and beyond on November 29th and enjoy live “Sounds of the Season” music from 12 – 4:30 PM\, featuring Melodic Outreach Endeavor (a group of talented Aragon High School musicians)! \nThe Downtown San Mateo Association is bringing special gifts for those who shop small in San Mateo!* Support your local community and enjoy the tunes. \n*While supplies last. Event details may change in case of inclement weather. URL:https://dsma.org/event/sounds-of-the-season-with-melodic-outreach-endeavor/ LOCATION:Downtown San Mateo CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2025/11/2025-Sounds-of-the-Season-Melodic-Outreach-Endeavor-Instagram-Post-45-2-e1763599480461.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;VALUE=DATE:20251128 DTEND;VALUE=DATE:20251213 DTSTAMP:20260521T184158 CREATED:20251125T193347Z LAST-MODIFIED:20251125T193724Z UID:10002942-1764288000-1765583999@dsma.org SUMMARY:Shop Small to Win Big in San Mateo DESCRIPTION:Brought to you by the Downtown San Mateo Association and the San Mateo Area Chamber of Commerce: \nIt’s time to celebrate San Mateo and support local businesses! \nSmall Business Saturday is a day dedicated to supporting small businesses and communities across the country and is part of the larger Shop Small Movement. Founded by American Express in 2010\, this day is celebrated each year on the Saturday after Thanksgiving in the U.S. \nWe know you already love and support the local businesses of San Mateo! That’s why the San Mateo Area Chamber of Commerce and the Downtown San Mateo Association (DSMA) want to thank you for “shopping small” this Small Business Saturday. \nParticipate for your chance to win prizes from Porterhouse\, Clawesome\, Fanloli Beauty\, Susan’s European Beauty\, Sports Basement\,  Elements Massage\, Avenida and more! \nStep 1:\nShop Small in San Mateo between November 28th and December 12th\, 2025! Make any purchase\, whether from a retail store\, restaurant\, grocer\, wellness provider\, fitness facility\, or any small business in the City of San Mateo. \nStep 2:\nFill out THIS FORM by December 13th at noon PT. 1 entry per person. \nStep 3:\nThe San Mateo Area Chamber of Commerce and DSMA will randomly draw winners from qualifying participants! Prizes include gift certificates from Porterhouse\, Fanloli Beauty\, Susan’s European Beauty\, Sports Basement\,  Elements Massage\, Avenida and more. Winners will be notified by email. \nThe deadline for entries is December 13th at noon PT. Winners will be randomly selected after entries have been verified. Winners will be notified via email and prizes can be mailed or picked up in person. \nIf you have issues completing this form\, please email hq@dsma.org or call (650) 342-5520 during regular business hours. URL:https://dsma.org/event/shop-small-to-win-big-in-san-mateo/ LOCATION:Downtown San Mateo CATEGORIES:Events,Promotions ATTACH;FMTTYPE=image/png:https://dsma.org/wp-content/uploads/2025/11/2025-small-business-Saturday-POSTCARD.png ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251111T090000 DTEND;TZID=America/Los_Angeles:20251111T100000 DTSTAMP:20260521T184158 CREATED:20250106T174057Z LAST-MODIFIED:20250616T172038Z UID:10001194-1762851600-1762855200@dsma.org SUMMARY:DSMA Board Meeting (Open to the Public) DESCRIPTION: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. \nIf you have questions or to confirm the meeting location\, please email us at HQ@dsma.org. \nIf you would like to make a presentation to the DSMA Board\, reach out by email at least one month before the scheduled meeting. URL:https://dsma.org/event/dsma-board-meeting-open-to-the-public/2025-11-11/ CATEGORIES:Events ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251025T150000 DTEND;TZID=America/Los_Angeles:20251025T170000 DTSTAMP:20260521T184158 CREATED:20250827T205005Z LAST-MODIFIED:20251025T220409Z UID:10002822-1761404400-1761411600@dsma.org SUMMARY:"Boo"s and Brews on B Street & Trick or Treating DESCRIPTION:Boos on B map\nJoin us on Saturday\, October 25 from 3:00-5:00pm in Downtown San Mateo on the Pedestrian Mall  on B Street between 1st and 3rd Avenue. \n\nTrick-or-treating\nKids Activities\nDragon Wagon Reptiles Petting Zoo\nArts and Crafts\nMusic\nPhoto Opportunities\n\n\n\n\n\n\n\n\n\n\n\n\n\nWear a costume and look FANG-tastic!\nGrab lunch first and head on over\, or enjoy the event then grab dinner! Costumes are welcomed and highly encouraged! This event is run by the City of San Mateo Parks and Recreation Department and the Downtown San Mateo Association and will be SPOOK-tacular! \n\n\n\n\n\n\n\n\n\nBusinesses Participating in Trick or Treat from 3-5pm:\nLook for the businesses with ghost decorations near their front entrances! All treats\, prizes\, activities\, and giveaways are first come\, first served\, while supplies last. \n\n \n \n \n \n \n \n\n Business NameAddress\n\n\n\n \n Taqueria Los Primos85 N B St #4 \n \n La Huerta Market142 N B St \n \n La Pinata Mexicatesen120 N B St \n \n Video Loco132 N B St \n \n Mi Rancho Supermarket80 N B St \n \n Snacks31 N B St \n \n Chill Spot Rendezvous271 Baldwin Ave \n \n Full Circle Barber308 Baldwin Ave \n \n Yi Fang110 S B ST \n \n Philz Coffee113 S B Street \n \n Anton SV Patisserie390 1st Ave \n \n Curry Pizza House135 S B St \n \n Revolution Hair Studio132 S B St \n \n Somisomi134 S B St \n \n Urban Ritual140 S B St \n \n FogBird144 S B Street \n \n Mountain Mike's Pizza154 S B St \n \n Fanloli Beauty159 S B St \n \n Atlas Skateboarding209 2nd Ave. \n \n Just for Optical200A 2nd Ave \n \n New Thai Elephant200 S B St \n \n Fire Wings206 S B St \n \n New York Pizza219 S B St \n \n Olhso House236 S B St \n \n Urban Momo254 S B St \n \n Heere Tea253 S B St \n \n Y Salon241 S San Mateo Dr \n \n Sweet Moment137 E 3rd Ave \n \n Nick the Greek213 3rd Ave \n \n Core Taekwondo86 E 3rd Avenue \n \n Simplycake132 E 3rd Ave \n \n Tri Counties Bank150 E 3rd Ave \n \n 3 Bees Cafe224 W 3rd Ave \n \n Avocado Toast226 E 3rd Ave \n \n Lions Den Shaveparlor236 E 3rd Ave \n \n Honey & Hive320 E 3rd Ave \n \n Scandinavian Designs317 S B St \n \n Mr Pizza Man201 E 4th Ave \n \n Nakoko335 E 4th Ave Ste A \n \n AAA Vacuum & Sewing501 S B St URL:https://dsma.org/event/save-the-date-boos-on-b-street-trick-or-treating/ LOCATION:Downtown San Mateo CATEGORIES:Events ATTACH;FMTTYPE=image/png:https://dsma.org/wp-content/uploads/2025/08/boosandbrews.png ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251019T110000 DTEND;TZID=America/Los_Angeles:20251019T170000 DTSTAMP:20260521T184158 CREATED:20250210T223826Z LAST-MODIFIED:20250210T223826Z UID:10001362-1760871600-1760893200@dsma.org SUMMARY:HEAD WEST Marketplace DESCRIPTION: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 this season! \nMore about HEAD WEST: \n\n\nHEAD 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 hand-made ceramics to locally sourced vintage\, there are always new categories of goods available to explore. Connecting people\, forging community + sustaining the local economy\, we continue to build upon our presence by offering expanded resources for small businesses to learn\, grow\, connect + share. Interested in applying to be a HEAD WEST vendor? Visit HEADWEST.com/apply \nNeed help finding your way to Downtown San Mateo? Visit our DIRECTIONS and PARKING pages \n*Event details may change due to inclement weather. URL:https://dsma.org/event/2025head-west-marketplace/2025-10-19/ LOCATION:South B Street\, South B Street (Between Baldwin Ave. & 2nd Ave.)\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/png:https://dsma.org/wp-content/uploads/2025/02/South-B-Street-1080x1080-copy.png ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251014T090000 DTEND;TZID=America/Los_Angeles:20251014T100000 DTSTAMP:20260521T184158 CREATED:20250106T174057Z LAST-MODIFIED:20250616T172038Z UID:10001193-1760432400-1760436000@dsma.org SUMMARY:DSMA Board Meeting (Open to the Public) DESCRIPTION: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. \nIf you have questions or to confirm the meeting location\, please email us at HQ@dsma.org. \nIf you would like to make a presentation to the DSMA Board\, reach out by email at least one month before the scheduled meeting. URL:https://dsma.org/event/dsma-board-meeting-open-to-the-public/2025-10-14/ CATEGORIES:Events ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20251004T130000 DTEND;TZID=America/Los_Angeles:20251004T150000 DTSTAMP:20260521T184158 CREATED:20250922T210137Z LAST-MODIFIED:20250930T163942Z UID:10002836-1759582800-1759590000@dsma.org SUMMARY:Jazz on B Street with Swingatto DESCRIPTION:Join us for Jazz on B Street on Saturday\, October 4th\, as we welcome Swingatto\, a dynamic Swing and Gypsy jazz trio\, to Downtown San Mateo! \nFrom 1-3pm\, let their lively melodies transport you to another era while you enjoy a delightful afternoon in the heart of Downtown. Don’t miss this chance to experience music that’s as vibrant as our community! \n**Event details may change due to inclement weather. \nDate: Saturday\, October 4th\nTime: 1:00 PM – 3:00 PM\nLocation: B Street (between 1st and 2nd Avenues) in Downtown San Mateo URL:https://dsma.org/event/jazz-on-b-street-with-swingatto-2/ LOCATION:B Street between 1st and 2nd avenues\, B Street between 1st and 2nd avenues\, San mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2025/09/20251004_JazzOnBStreet-Instagram-Post-45-e1758574856778.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250921T110000 DTEND;TZID=America/Los_Angeles:20250921T170000 DTSTAMP:20260521T184158 CREATED:20250210T223826Z LAST-MODIFIED:20250210T223826Z UID:10001361-1758452400-1758474000@dsma.org SUMMARY:HEAD WEST Marketplace DESCRIPTION: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 this season! \nMore about HEAD WEST: \n\n\nHEAD 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 hand-made ceramics to locally sourced vintage\, there are always new categories of goods available to explore. Connecting people\, forging community + sustaining the local economy\, we continue to build upon our presence by offering expanded resources for small businesses to learn\, grow\, connect + share. Interested in applying to be a HEAD WEST vendor? Visit HEADWEST.com/apply \nNeed help finding your way to Downtown San Mateo? Visit our DIRECTIONS and PARKING pages \n*Event details may change due to inclement weather. URL:https://dsma.org/event/2025head-west-marketplace/2025-09-21/ LOCATION:South B Street\, South B Street (Between Baldwin Ave. & 2nd Ave.)\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/png:https://dsma.org/wp-content/uploads/2025/02/South-B-Street-1080x1080-copy.png ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250909T090000 DTEND;TZID=America/Los_Angeles:20250909T100000 DTSTAMP:20260521T184158 CREATED:20250106T174057Z LAST-MODIFIED:20250616T172038Z UID:10001192-1757408400-1757412000@dsma.org SUMMARY:DSMA Board Meeting (Open to the Public) DESCRIPTION: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. \nIf you have questions or to confirm the meeting location\, please email us at HQ@dsma.org. \nIf you would like to make a presentation to the DSMA Board\, reach out by email at least one month before the scheduled meeting. URL:https://dsma.org/event/dsma-board-meeting-open-to-the-public/2025-09-09/ CATEGORIES:Events ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250817T110000 DTEND;TZID=America/Los_Angeles:20250817T170000 DTSTAMP:20260521T184158 CREATED:20250210T223826Z LAST-MODIFIED:20250210T223826Z UID:10001360-1755428400-1755450000@dsma.org SUMMARY:HEAD WEST Marketplace DESCRIPTION: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 this season! \nMore about HEAD WEST: \n\n\nHEAD 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 hand-made ceramics to locally sourced vintage\, there are always new categories of goods available to explore. Connecting people\, forging community + sustaining the local economy\, we continue to build upon our presence by offering expanded resources for small businesses to learn\, grow\, connect + share. Interested in applying to be a HEAD WEST vendor? Visit HEADWEST.com/apply \nNeed help finding your way to Downtown San Mateo? Visit our DIRECTIONS and PARKING pages \n*Event details may change due to inclement weather. URL:https://dsma.org/event/2025head-west-marketplace/2025-08-17/ LOCATION:South B Street\, South B Street (Between Baldwin Ave. & 2nd Ave.)\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/png:https://dsma.org/wp-content/uploads/2025/02/South-B-Street-1080x1080-copy.png ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250816T170000 DTEND;TZID=America/Los_Angeles:20250816T183000 DTSTAMP:20260521T184158 CREATED:20250814T170942Z LAST-MODIFIED:20250814T170942Z UID:10002079-1755363600-1755369000@dsma.org SUMMARY:Pop Up performance on North B Street: Reyna y su Trio DESCRIPTION:Date: August 16th\nTime: 5:00 – 6:30 PM\nLocation: Starting at 100 South B Street (in front of Orange Theory)\, Reyna y su Trio will make multiple stops as they move north on North B Street \nEnjoy an evening of vibrant music on North B Street with Reyna y su Trio\, performing classic Mexican and Latin songs that will have you swaying\, singing\, and smiling. This talented trio will stroll to multiple locations\, filling the street with boleros\, rancheras\, cumbias\, and more. \n*Event details may change due to inclement weather. URL:https://dsma.org/event/pop-up-performance-on-north-b-street-reyna-y-su-trio/ LOCATION:North B Street\, North B Street & Tilton Avenue\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2025/08/B-Street-Music-Pop-Up-Reyna-y-su-trio.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250812T090000 DTEND;TZID=America/Los_Angeles:20250812T100000 DTSTAMP:20260521T184158 CREATED:20250106T174057Z LAST-MODIFIED:20250616T172038Z UID:10001191-1754989200-1754992800@dsma.org SUMMARY:DSMA Board Meeting (Open to the Public) DESCRIPTION: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. \nIf you have questions or to confirm the meeting location\, please email us at HQ@dsma.org. \nIf you would like to make a presentation to the DSMA Board\, reach out by email at least one month before the scheduled meeting. URL:https://dsma.org/event/dsma-board-meeting-open-to-the-public/2025-08-12/ CATEGORIES:Events ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250803T120000 DTEND;TZID=America/Los_Angeles:20250803T140000 DTSTAMP:20260521T184158 CREATED:20250701T190533Z LAST-MODIFIED:20250702T165019Z UID:10001660-1754222400-1754229600@dsma.org SUMMARY:All Aboard! The Downtown Express DESCRIPTION:Downtown San Mateo Association & Florian Orthodontics present: The Downtown Express \nDate: August 3rd\nTime: 12:00 – 2:00 PM\nLocation: 222 E 4th Ave (Farmer’s Market at the former Draegers Parking Lot) in Downtown San Mateo \nThe Downtown Express! Bringing smiles to Downtown San Mateo with FREE train rides and treats at the Farmer’s Market* on Sunday\, August 3 from noon-2pm! \nSee you there! \n*Event details may change due to inclement weather. Rides and giveaways will be first come\, first served. URL:https://dsma.org/event/all-aboard-the-downtown-express/ LOCATION:Draeger’s\, 222 E 4th Ave\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2025/07/Locomotive-Train-Transportation-Logo-1.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250720T110000 DTEND;TZID=America/Los_Angeles:20250720T170000 DTSTAMP:20260521T184158 CREATED:20250210T223826Z LAST-MODIFIED:20250210T223826Z UID:10001359-1753009200-1753030800@dsma.org SUMMARY:HEAD WEST Marketplace DESCRIPTION: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 this season! \nMore about HEAD WEST: \n\n\nHEAD 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 hand-made ceramics to locally sourced vintage\, there are always new categories of goods available to explore. Connecting people\, forging community + sustaining the local economy\, we continue to build upon our presence by offering expanded resources for small businesses to learn\, grow\, connect + share. Interested in applying to be a HEAD WEST vendor? Visit HEADWEST.com/apply \nNeed help finding your way to Downtown San Mateo? Visit our DIRECTIONS and PARKING pages \n*Event details may change due to inclement weather. URL:https://dsma.org/event/2025head-west-marketplace/2025-07-20/ LOCATION:South B Street\, South B Street (Between Baldwin Ave. & 2nd Ave.)\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/png:https://dsma.org/wp-content/uploads/2025/02/South-B-Street-1080x1080-copy.png ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250622T110000 DTEND;TZID=America/Los_Angeles:20250622T130000 DTSTAMP:20260521T184158 CREATED:20250609T195843Z LAST-MODIFIED:20250609T201621Z UID:10001483-1750590000-1750597200@dsma.org SUMMARY:Summer Splash (with SF Bay Area Moms & Downtown San Mateo Association) DESCRIPTION: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! \nThis event is free with complimentary parking nearby. Come hang out\, grab a bite\, and celebrate the start of summer! Activities and goodies will be offered while supplies last\, come early for the best opportunity to participate! URL:https://dsma.org/event/summer-splash/ LOCATION:B Street between 1st and 2nd avenues\, B Street between 1st and 2nd avenues\, San mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2025/06/504103000_1382641012807826_8314542774766896249_n.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250615T110000 DTEND;TZID=America/Los_Angeles:20250615T170000 DTSTAMP:20260521T184158 CREATED:20250210T223826Z LAST-MODIFIED:20250210T223826Z UID:10001358-1749985200-1750006800@dsma.org SUMMARY:HEAD WEST Marketplace DESCRIPTION: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 this season! \nMore about HEAD WEST: \n\n\nHEAD 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 hand-made ceramics to locally sourced vintage\, there are always new categories of goods available to explore. Connecting people\, forging community + sustaining the local economy\, we continue to build upon our presence by offering expanded resources for small businesses to learn\, grow\, connect + share. Interested in applying to be a HEAD WEST vendor? Visit HEADWEST.com/apply \nNeed help finding your way to Downtown San Mateo? Visit our DIRECTIONS and PARKING pages \n*Event details may change due to inclement weather. URL:https://dsma.org/event/2025head-west-marketplace/2025-06-15/ LOCATION:South B Street\, South B Street (Between Baldwin Ave. & 2nd Ave.)\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/png:https://dsma.org/wp-content/uploads/2025/02/South-B-Street-1080x1080-copy.png ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250610T090000 DTEND;TZID=America/Los_Angeles:20250610T100000 DTSTAMP:20260521T184158 CREATED:20250604T171600Z LAST-MODIFIED:20250604T171602Z UID:10001189-1749546000-1749549600@dsma.org SUMMARY:DSMA Board Meeting (Open to the Public) DESCRIPTION: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. \nIf you have questions or to confirm the meeting location\, please email us at HQ@dsma.org. \nIf you would like to make a presentation to the DSMA Board\, reach out by email at least one month before the scheduled meeting. URL:https://dsma.org/event/dsma-board-meeting-open-to-the-public-2/ LOCATION:Chill Spot Rendezvous\, 271 Baldwin Ave.\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250518T110000 DTEND;TZID=America/Los_Angeles:20250518T170000 DTSTAMP:20260521T184158 CREATED:20250210T223826Z LAST-MODIFIED:20250210T223826Z UID:10001357-1747566000-1747587600@dsma.org SUMMARY:HEAD WEST Marketplace DESCRIPTION: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 this season! \nMore about HEAD WEST: \n\n\nHEAD 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 hand-made ceramics to locally sourced vintage\, there are always new categories of goods available to explore. Connecting people\, forging community + sustaining the local economy\, we continue to build upon our presence by offering expanded resources for small businesses to learn\, grow\, connect + share. Interested in applying to be a HEAD WEST vendor? Visit HEADWEST.com/apply \nNeed help finding your way to Downtown San Mateo? Visit our DIRECTIONS and PARKING pages \n*Event details may change due to inclement weather. URL:https://dsma.org/event/2025head-west-marketplace/2025-05-18/ LOCATION:South B Street\, South B Street (Between Baldwin Ave. & 2nd Ave.)\, San Mateo\, CA\, 94401\, United States CATEGORIES:Events ATTACH;FMTTYPE=image/png:https://dsma.org/wp-content/uploads/2025/02/South-B-Street-1080x1080-copy.png ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250513T090000 DTEND;TZID=America/Los_Angeles:20250513T100000 DTSTAMP:20260521T184158 CREATED:20250106T174057Z LAST-MODIFIED:20250616T172038Z UID:10001188-1747126800-1747130400@dsma.org SUMMARY:DSMA Board Meeting (Open to the Public) DESCRIPTION: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. \nIf you have questions or to confirm the meeting location\, please email us at HQ@dsma.org. \nIf you would like to make a presentation to the DSMA Board\, reach out by email at least one month before the scheduled meeting. URL:https://dsma.org/event/dsma-board-meeting-open-to-the-public/2025-05-13/ CATEGORIES:Events ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT BEGIN:VEVENT DTSTART;TZID=America/Los_Angeles:20250511T120000 DTEND;TZID=America/Los_Angeles:20250511T140000 DTSTAMP:20260521T184158 CREATED:20250417T173859Z LAST-MODIFIED:20250422T215714Z UID:10001438-1746964800-1746972000@dsma.org SUMMARY:Mother's Day in Downtown San Mateo DESCRIPTION:Treat your the moms in your life this Mother’s Day! As an added incentive to celebrate Mother’s Day in Downtown San Mateo\, DSMA and Lion’s Den Shaveparlor are hosting the following: \n\nLive music from Makule from noon-2pm on B Street\nFloral Selfie wall starting at noon in front of 3 Bees Coffee\nThe first 100 moms to stop by the selfie wall will get flowers\, thanks to the generosity of Edmond’s Plaza Florist.\n\nMom of 3\, mom-to-be\, dog mom\, grandma– moms of all types are welcome! \nNeed help deciding where to make brunch or dinner reservations? Peruse our Downtown San Mateo Restaurant Guide! \n*Details may change in case of Inclement weather. Flowers are first come\, first served\, while supplies last. URL:https://dsma.org/event/mothers-day-in-downtown-san-mateo/ CATEGORIES:Events ATTACH;FMTTYPE=image/jpeg:https://dsma.org/wp-content/uploads/2025/04/square-Mothers-Day-pop-up-2025-1.jpg ORGANIZER;CN="Downtown San Mateo Association":MAILTO:HQDSMA@gmail.com END:VEVENT END:VCALENDAR