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Boba and Bunnies Downtown in April

Downtown was really hopping in March. There was Jazz on B Street, a Ukulele Jam, HEAD WEST Marketplace, the weekly Downtown San Mateo Farmers Market, live music, karaoke, trivia, comedy, dance, free yoga, and secret movies. We’ve also had quite a few new businesses join our neighborhood, so you’ll want to come check us out soon!

April is going to be so much fun: HEAD WEST Marketplace returns to B Street, and we’ll be hosting our third annual Boba Day, which is always a HUGE event. There will also be two opportunities to meet the Easter Bunny, an entire week celebrating libraries, and more comedy, live music, karaoke, and dance.



Don’t forget to follow us on Facebook and Instagram for the latest updates. Do you know that we post reviews of local businesses, and Secrets of San Mateo? You’ll learn about some of our quieter neighbors, and also about movie discounts, chocolate sourdough, loaner sewing machines, half-price sushi, and more.

We have an Events Calendar, Restaurant Guide, Deals and Promotions page, a Walking Tour, and an archive of our past newsletters, on DSMA.org.

Thank you for your support of our small business community!

Downtown San Mateo Boba Day

Calling all boba enthusiasts! Join us on Sunday, April 26th (12 – 3 PM) for a day dedicated to everyone’s favorite pearl-filled drinks. Downtown San Mateo boba shops and other retailers will be rolling out the red carpet with special deals and giveaways you won’t want to miss. While you’re sipping, explore the community booths and family-friendly activities along B Street.

Extra excitement begins at 1 PM with a Live Judging event featuring Chef Martin Yan, Wendy Hsu, and Mayor Adam Loraine. Watch them put the best local brews to the test! Don’t forget to swing by the Downtown San Mateo Association booth to vote for your own favorite shop and show your boba receipt to claim a special event prize. We’ll see you there!

Learn more here.

Eggstravaganza

It’s the 49th year for Eggstravaganza at Central Park! Join the spring bunny on Saturday, April 4, for this eggcellent family-fun spring-themed event. Enjoy kid-friendly activities, live entertainment, egg hunts, and more.

Find more information here.

HEAD WEST Marketplace

HEAD WEST Marketplace returns to B Street on Saturday, April 18, from 11am to 5pm.

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 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!

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

Restaurant Week

Flavors of the Peninsula is a 10-day restaurant celebration featuring prix-fixe menus throughout the Peninsula.

Scheduled for Thursday, April 23-Sunday, May 3, the event will showcase restaurants throughout San Mateo County. Participating restaurants will offer specially curated menus, making the Peninsula’s culinary excellence accessible to both residents and visitors across multiple price points.

Downtown restaurants include Amici’s, Avenida, B Street & Vine, Chill Spot Rendezvous, Curry Pizza House, Joy Sushi, Pacific Catch, Pausa, Porterhouse, and Tokie’s.

This promotion is put on by The SF Peninsula, an organization that promotes tourism in San Mateo County. Find more information on their website.

• April 1 – Sunset Trivia (O’Neill’s)(every Wednesday)
• April 2 – Uncorked Comedy (A2 Wine Bar)
• April 2 – Wildstyle Karaoke (McGoverns)(every Thursday)
• April 3 – Good Friday Baccala Luncheon (Peninsula Italian American Social Club)
• April 4 – Cocktail Masters Class (Fogbird)
• April 5 – Easter Egg Hunt (Kiddo Adventure Indoor Playground)
• April 5 – Wildstyle Karaoke (McGoverns)(every Sunday)
• April 6 – Swing Social (Motion Arts Center)
• April 7 – Trivia Tuesdays (McGoverns)(every Tuesday)
• April 10 – Monthly Friday Night Dinner Dance (Peninsula Italian American Social Club)
• April 11 – Musicale: A Recital featuring Young Bay Area Music and Dance Students (Main Library)
• April 11 – Texas Hold’Em Poker Tournament (Peninsula Italian American Social Club)
• April 12 – Visit to Mission Farm / Master Gardener Plant Clinic (San Mateo Arboretum Society)
• April 19-25 – San Mateo Celebrates! (San Mateo Public Library Foundation)
• April 20 – An Evening with Kevin Blake, Magician Extraordinaire (Italian American Womens Guild/Peninsula Italian American Social Club)
• April 24 – Monte Carlo – Night in Italy (Peninsula Italian American Social Club)
• April 25 – Wedding First Dance Workshop / Salsa Footwork and Styling Workshop (Motion Arts Center)
• April 25 – Mixology 101 Class (Fogbird)
• April 25 – Live Music: Power Chord (McGoverns)
• May 30 – Save the Date: Love Local

Central Park

• Amici’s will team with your school or community group to hold a fundraising event. Plan your event on a designated Monday or Tuesday, and they’ll donate back 25% of the dine-in and pick-up sales from your group to the cause of your choice. Learn more here

• Cinemark Century San Mateo 12 has Discount Tuesdays with 50% off tickets

• Peninsula Dance Academy is now enrolling for the 2026-2027 season and competition team

• TinyB Chocolate recently took chocolates to senior residences in San Mateo County, and residents were invited to taste test treats

• Whisper is open for dinner (5-9pm Monday-Thursday, 5-9:30pm Friday-Saturday)

• Vote for your favorite Downtown business in the 2026 Best of San Mateo awards hosted by the San Mateo Area Chamber of Commerce

• Welcome to the neighborhood: Blue Moon Bar, Bueno Brows, Footwork, Johnny’s, MIXT, Shang Dumpling, Shiloh Aesthetics, Top Time Dance Studio

Share feedback on the future of El Camino Real

Help shape safer walking, biking, driving & transit by taking a short survey for the Central El Camino Real Multimodal Plan, led by SamTrans with San Mateo & partner cities. Take the survey today

Supporting Neighbors Through the Shutdown: Local Food Resources & Ways to Help

If the federal shutdown is affecting your CalFresh benefits, you’re not alone. Find out where San Mateo residents can turn for immediate food support and relief. Click for local food resources

Stay Connected with the City — Introducing My San Mateo

Want an easier way to report issues, request City services, and stay connected—all in one place? The My San Mateo App and Website is your hub for quick, convenient civic engagement.

With My San Mateo, you can:

• Report issues like potholes, broken streetlights, and more
• Track the status of your service requests in real time
• Receive notifications when there are updates
• Stay connected and help keep San Mateo running smoothly—from your phone or computer

Whether you’re out in the neighborhood or at home, My San Mateo makes it simple to stay informed and take action. Visit the website to learn more

Pedestrian Safety Improvements Downtown

New pedestrian safety barriers were installed in March on 1st & 3rd Avenues and B Street.

These barriers are at the intersection of the pedestrian mall where vehicle exposure is highest, giving pedestrians extra protection. Nearby, blue bike-locker–style cabinets let City staff move and manage the barriers as needed. These enhancements help keep our Downtown vibrant and safe for everyone who lives, works, and visits here

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)

• Theflowspace.com – The 13 Best Shapewear Leggings For Comport and Support (Holly Roser Fitness)
• Hoodline – Half Moon Bay Brunch Star Johnny’s Quietly Muscles into Downtown San Mateo
• The Mercury News – Half Moon Bay brunch spot opens new location in San Mateo (Johnny’s)
• The Mercury News – New Asian fusion brunch spot now open in San Mateo (Whisper)
• The Mercury News – High-end Mexican restaurant opens second location on Peninsula (Reposado)
• The Mercury News – How all those Valentine’s bon bons get made at Bay Area chocolate shops (Sharona’s Chocolate Shop)
• The New York Times – For a Simpler Workout, Try Combining Moves (Holly Roser Fitness)
• San Francisco Chronicle – A cult-favorite Chinese bakery is opening its first Peninsula location (Pineapple King Bakery)
• San Mateo Daily Journal – A story in resilience: 2nd San Mateo location has become a success (Rise Woodfire)
• San Mateo Daily Journal – Bueno Brows reshaping beauty service experience
• Scot Scoop – From home digest: Molly Tea edition