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Celebrate Spring with Us Downtown

February brought great energy to Downtown San Mateo! From the San Mateo Sports Warm Up (pictured above) and Big Game watch parties to live music, karaoke, stand-up comedy, and the Downtown San Mateo Farmers Market, there was something for everyone.

March is the official arrival of spring! The longer days make it a perfect time to enjoy some outdoor events like Jazz on B Street, a Ukulele Jam, and the always-fun HEAD WEST Marketplace.

We hit an exciting milestone in February– 10,000 Facebook followers! Be sure to follow us there and on Instagram for the latest updates.

Have you looked at DSMA.org? We have an Events Calendar, Restaurant Guide, Deals and Promotions page, a Walking Tour, and an archive of our past newsletters.

We always appreciate your support of our small business community!

Jazz on B Street

Head Downtown on Sunday, March 1, for live Jazz on B Street. The Birds, a group of musicians from Aragon High School, will be playing from 1-3pm.

Make an afternoon of it and enjoy lunch or your favorite drink from one of our 150+ restaurants in Downtown San Mateo.

*Event details may change in case of inclement weather

Ukulele Jam

Our Ukulele Jam in 2024 was so much fun that we decided to do it again! Bring your uke to B Street on Saturday, March 14, and join us for a fun-filled gathering led by San Mateo musicians Charlie Chin and Victor Labrador.

A limited number of ukuleles will be available to borrow, thanks to the San Mateo Public Library.

*Event details may change in case of inclement weather. Borrowed ukuleles will be available on a first-come, first-served basis

HEAD WEST Marketplace Returns

HEAD WEST Marketplace is returning for a second year of marketplaces starting Saturday, March 21, from 11am to 5pm.

The Marketplace will be held on the third Saturday of each month, March-December. (Note that the event has been moved to Saturday rather than Sunday.)

Apply now to join the HEAD WEST Family of local makers, crafters, artists, designers, and small biz merchants for 2026 dates.

San Mateo Sports Warm-Up Recap

Thanks for coming out to our San Mateo Sports Warm Up on Saturday, February 7. The free, family-friendly afternoon featured a special appearance by the back-to-back State Champion CSM Bulldogs. Attendees met players from the College of San Mateo’s football team, and then tested their own skills on the Perform for Golf putting green, foosball and ping pong tables, the San Mateo Parks & Rec mobile games, and more. There was also a live demo from the Belmont Brass Wrists Arm Wrestling Club. 

Thanks to our partner, Perform for Golf, and to the San Mateo Area Chamber of Commerce, the City of San Mateo, the City of San Mateo’s Parks and Recreation Department, CSM, and the Brass Wrists.

• March 1 – Gratitude Meditation (Chill Spot Rendezvous)
• March 1 – Camellias / Master Gardener Plant Clinic (San Mateo Arboretum Society)
• March 1 – Wildstyle Karaoke (McGoverns)(every Sunday)
• March 2 – Swing Social (Motion Arts Center)
• March 3 – Full Moon Chanting and Meditation (Tree of Life Healing Center for the Soul)
• March 3 – Trivia Tuesdays (McGoverns)(every Tuesday)
• March 4 – Sunset Trivia (O’Neill’s)(every Wednesday)
• March 6 – Live Music: Stone Temple Parents (McGoverns)
• March 6 – Karaoke (Chill Spot Rendezvous)(every Friday)
• March 6 – First Friday Dinner Dance (Peninsula Italian American Social Club)
• March 6 – Latin Night Social Party (Motion Arts Center)(every Friday)
• March 7 – Help Beautify Central Park’s Rose Garden (San Mateo Arboretum Society)
• March 7 – Wedding First Dance Workshop (Motion Arts Center)
• March 7 – Milonga Tango Party (Motion Arts Center)(every Saturday)
• March 14 – Fairy Garden Workshop (San Mateo Arboretum Society)
• March 15 – Nowruz (Main Library)
• March 15 – Sunday Funday: Irish Whiskey Tasting Event (Fogbird)
• March 21 – Live Music: WindSync (Main Library)
• March 21- Mixology 101: Classic Cocktails Class (Fogbird)
• March 21 – Ladies Styling & Heels Dance Workshop (Motion Arts Center)
• March 21 – Venetian Carnevale Extravaganza (Peninsula Italian American Social Club)
• March 22- Community Coffee with Council Member Lisa Diaz Nash (3 Bees Coffee)
• March 22 – Exclusive Screening: A Little Fellow – The Legacy of A.P. Giannini (Peninsula Italian American Social Club)
• March 25 – Montenegro Happy Hour Take Over (Fogbird)
• March 25 – SF Giants Opening Night Watch Party (Peninsula Italian American Social Club)
• March 29 – Community Free Mat Pilates: Classic Flow-Return to Life (Lucent Pilates)
• March 29 – Crab Feed (Peninsula Italian American Social Club)
• April 4 – Save the Date: Eggstravaganza
• April 20 – An Evening with Kevin Blake, Magician Extraordinaire (Italian American Womens Guild/Peninsula Italian American Social Club)
• April 26 – Save the Date: Downtown San Mateo Boba Day

South B St.

• Aikido by the Bay is offering a Kids Summer Camp this year

• Each month, Amici’s has 20% off items of the month. Check out their Instagram page for their specials for March

• B Street & Vine is now open Mondays 5-9pm, and has a great Sangria Mondays deal

• Colander Kitchens is open Monday-Friday, 9am-2:30pm. They also have a new brunch menu of southern breakfast favorites with New Orleans soul

• MIXT‘s newest location will open in Downtown San Mateo on Tuesday, March 3! Join them for a week of special giveaways and promotions.

• Motion Arts Center has added new classes, including Line Dancing, Bachata Couples Only, and Argentine Tango Couples Only Basics

• Congratulations, Peninsula Family Service, on being awarded a grant by The Chan Zuckerberg Initiative’s Community Fund!

• The Kohl Pumphouse at Central Park is available to rent for events. Contact the San Mateo Arboretum Society here

• Nominations are open for the 2026 Best of San Mateo awards hosted by the San Mateo Area Chamber of Commerce. Nominate your favorite Downtown San Mateo business today!

• TinyB Chocolate hosts kids’ birthday parties

• Welcome to the neighborhood: Le Muller, Reposado

Downtown Safety Enhancements – 1st and 3rd Avenues

New safety enhancements on 1st Avenue and 3rd Avenue are being implemented to improve safety and comfort for everyone who lives, works, and visits Downtown. The new safety barriers will replace the existing planter barriers. Installation of new safety barriers is scheduled for Wednesday, March 4

Storm & Flood Preparedness

Sandbag stations are now open! Find information about sandbags, and preparation and safety tips on the City’s Storm & Flood Preparedness page

Free Downtown Parking

Parking is FREE Downtown on Sundays and after 6pm every day. Find more information here. (Please note that this does not apply to private lots)

• Hoodline – MIXT moves into former B Street Books spot with weeklong San Mateo swag fest
• Mercury News –A week of festivities is on tap at this fast-casual spot’s upcoming San Mateo opening (MIXT)
• NBC10 – What do people in Tom Brady’s hometown have to say about the GOAT? (3 Bees Coffee)
• San Francisco Chronicle – The Bay Area’s 25 best restaurants of the moment (Tai Er)
• San Francisco Chronicle – Top Affordable Dining (Kajiken)
• San Mateo Daily Journal – Prometheus’ downtown presence grows (Club Pilates, Reposado, Squeeze Massage)
• San Mateo Daily Journal – Downtown San Mateo Association welcomes new president (3 Bees Coffee)