August News and Events in Downtown San Mateo



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Downtown San Mateo Association Community

News

AUGUST 2026

Trains and Pups: August Downtown

What a fun and busy month July was! We had our second Soccer Social Pop-Up, 4th of July in the Park, a celebration of our newest mural, Bay Area Fit Fest, San Francisco Bay Area Moms Back-to-School Bash, and Jazz on B Street with Melodic Outreach Endeavor. There was also a Downtown Historic District Walking Tour, the Central Park Music Series, and our monthly HEAD WEST Marketplace.

Local businesses hosted soccer watch parties, live music, comedy shows, dance parties, trivia, and karaoke.

This month brings us the Downtown Express, the final concert of the Central Park Music Series, Central Bark, a Paw-fect Match Adoption Pop-Up Event, and HEAD WEST returns to B Street.

Follow us on Facebook and Instagram so you don’t miss a thing. You can also head over to DSMA.org, which serves as your ultimate Downtown guide. There, you can explore our Events Calendar, Restaurant Guide, and a Historic Walking Tour. Our past newsletters are even hanging out in our archive. Thank you for continuing to show up for our small business community!

P.S. If you missed it, we were featured on ABC7News! Read about it, and see the video here: Downtown San Mateo’s revival is a playbook for other California cities.

Downtown Express

Join us on Sunday, August 2, from 1-3pm, for a day of free family fun at 222 E. 4th Ave. (Draeger’s parking lot).

What to expect:

– Free train rides for all ages!

– Face painting by Core Taekwondo

Clawesome claw machine games

Everything is first-come, first-served while supplies last, so make sure to get there early. See you there!

Paw-fect Match Adoption Pop-Up

Find Your Paw-fect Match!

Looking to add a furry (or feathered!) friend to your family? Join us for the Paw-fect Match Adoption Pop-Up Event on Sunday, August 23, from 1-3pm on B Street (at 1st Ave). Presented by the Downtown San Mateo Association and the Peninsula Humane Society & SPCA, this is a great chance to meet potential pets, ask questions, and submit an adoption application.

Note: Animals will not be going home directly from the event, but you can start the application process on-site!

Central Bark

San Mateo PAL is holding their Central Bark event on Sunday, August 16, 12-3pm, at Central Park. Celebrate our furry friends with an afternoon packed with vendors, fun activities and lively entertainment.

All proceeds from Central Bark will go towards supporting San Mateo PAL youth programs.

Find more info here.

HEAD WEST Marketplace

HEAD WEST Marketplace returns to B Street on Saturday, August 15, from 11am to 5pm.

Visit B Street for HEAD WEST Marketplace on the third Saturday of every month. 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 this year’s dates.

Image: Mia Torres

More Upcoming Events

Downtown Business Updates

Hope Mural

  • Check out Amici’s monthly promotions on their social media. Promo is valid on orders placed via amicis.com or the mobile app. No code needed
  • B Street Boxing is not just about boxing. Fitness goals, weight loss, or any level of boxing competition, they’ve got you covered. Try a class today. Your first week is FREE!



  • Renew Salon has a brand-new online store. You can now skip the generic marketplace scroll and shop your exact, stylist-approved hair care formulas directly from them, any time you need them. No counterfeits. No guesswork. Just professional-grade results delivered straight to your door

  • BBQ Beef Back Ribs are now available all day, every day, at Rise Woodfire

City of San Mateo Announcements

Join San Mateo’s 2026 City Services Academy

Ever wondered what it takes to run a city? Here’s your chance to find out. The City of San Mateo’s City Services Academy is a free, hands-on experience that puts you face-to-face with the people who keep San Mateo running, including the City Manager, department directors, and City Council Members. You’ll tour City facilities, dig into real case studies, and get an inside look at the decisions shaping your community.

Whether you’re a curious neighbor, an aspiring public servant, or just want to know how your city really works, the academy is a special opportunity to learn more and engage with the City of San Mateo.

  • Applications due Wednesday, August 5
  • Dates: Wednesdays, 6-9pm, August 19-November 4 (no class September 30)
  • Free of cost and applications are open to anyone 16+ who lives or works in San Mateo
  • Apply now and learn more

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

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)

Downtown San Mateo in the News

Downtown San Mateo Association

Phone: (650) 342-5520

HQ@dsma.org

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