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September Downtown: Festivals & Marketplaces

It’s been such an incredible, lively summer in Downtown San Mateo! In August, our neighborhood hosted 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 Marketplace.

September will bring fun fall events like a Movie in the Park, Dine & Discover Downtown San Mateo, two September Nights on B Street, the return of HEAD WEST Marketplace, and September Arts & Culture Fest.

Every month, our Downtown businesses host live music, comedy shows, dance parties, trivia, and karaoke.

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!

September Nights on B Street

Spend your evening on B Street on September 10 and 17, where live music, great food, and family-friendly activities bring the block to life! Join the fun between 1st and 3rd Ave. from 6–8pm, featuring the following musical performances: 

• Thursday, September 10 – Live music by Pure Ecstasy (Motown & R&B) 
• Thursday, September 17 – Live music by Neon Velvet (Top 40) 

The whole family can come and enjoy the evening with a dedicated kids zone.

Details here.

Presented by the City of San Mateo, and supported by the San Mateo Area Chamber of Commerce and Downtown San Mateo Association.

HEAD WEST Marketplace

HEAD WEST Marketplace returns to B Street on Saturday, September 19, 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

September Arts & Culture Fest

Join us in the heart of Downtown San Mateo for a fun day-long celebration of art, music, dance, poetry, food, and culture! From live bands and dazzling cultural performances to interactive kids’ activities, LIVE mural painting competitions, artists selling original handcrafted artworks, and poetry open mic, the September Arts & Culture Fest has something for everyone — and it’s completely FREE to attend.

Find more information here.

September Arts & Culture Fest is presented by the San Mateo Area Chamber of Commerce, SMC Office of Arts and Culture, & Downtown San Mateo Association.

Dine & Discover Downtown San Mateo

Taste your way through downtown with Dine & Discover Downtown San Mateo, running September 10–30! Presented by the DSMA and the City of San Mateo, this campaign makes it easy to support local eateries while discovering new favorite spots. Just check in at participating restaurants as you dine to unlock points and win prizes. 

Prizes* include: 
- BOGO 50% off at 3 Bees Coffee
- Gift certificates for Downtown businesses
- Downtown San Mateo branded campfire mugs
- $500 gift certificate for Christensen & Rafferty Fine Jewelry

Keep an eye on our social media over the coming weeks as we roll out more details!

*Terms and conditions may apply.

• September 1 – Trivia Night (McGoverns)(every Tuesday)
• September 1 – Karaoke (O’Neill’s)(every Tuesday)
• September 2 – Trivia (O’Neill’s)(every Wednesday and Saturday)
• September 2 – Karaoke (Blue Moon Bar)(every Wednesday and Friday)
• September 3 – Karaoke (McGoverns)(every Sunday and Thursday)
• September 4 – Bachata/Salsa Social Dance Party (Motion Arts Center)(every Friday)
• September 4 – DJ Set (O’Neill’s)(every Friday)
• September 4 – Movies in the Park (Central Park)
• September 4 – Monthly Friday Night Dinner Dance (Peninsula Italian American Social Club)
• September 5 – The Art of the Arch: Exploration of Backbends (Nandi Yoga)
• September 5 – 75th Anniversary Series (Christian Science Reading Room)(also September 12, 19)
• September 6 – Growing Orchids / Master Gardener Plant Clinic (San Mateo Arboretum Society)
• September 6 – Gratitude Meditation (Chill Spot Rendezvous)
• September 7 – Secret Movie Series (Cinemark Century San Mateo 12)
• September 8 – Dance/Movement Therapy Support Group (Tree of Life Healing Center for the Soul)(also September 15, 22, 29)
• September 9 – Woodwind Madness with the Four Woods (Main Library)
• September 10 – September Nights on B Street (also September 17)
• September 11 – 9/11 Remembrance Ceremony (Fire Station 21)
• September 12 – Author Visit: Vero Perez (Main Library)
• September 12 – Wedding First Dance Workshop (Motion Arts Center)
• September 12 – Cozy Coloring Club Coloring Session & Picnic (Central Park)
• September 12 – San Mateo Firefighters Association Chili Cook-Off (Central Park)
• September 12 – Workshop with World Tango Champions Carla Rossi & Jose Luis Salvo / Milonga with Live Music by Orquesta Tarareando (Motion Arts Center)
• September 12 – Toscana Night (Peninsula Italian American Social Club)
• September 13 – Yin & Sound: Myofascial Release & Nervous System Reset (Nandi Yoga)
• September 14 – Secret Movie Series (Cinemark Century San Mateo 12)
• September 18-20 – Friends of the San Mateo Public Library Annual Fall Book Sale (Main Library)
• September 18-20 – Aikido Seminar: Preserving the Legacy (Aikido by the Bay)
• September 18 – Steaks & Stogies (Peninsula Italian American Social Club)
• September 19 – Autumn Moon Festival (Central Park)
• September 19 – Cocktail Masters Class: Advanced Mixology (Fogbird)
• September 19 – BTS K-Pop All Levels Workshop (Motion Arts Center)
• September 20 – 75th Anniversary Open House (Christian Science Reading Room)
• September 20 – British Invasion: A Family Friendly Evening of Dinner & Dance (Peninsula Italian American Social Club)
• September 25 – PIASC Goes Country (Peninsula Italian American Social Club)
• September 26 – September Arts & Culture Fest
• September 27 – Takahashi Market 120th Anniversary Party
• October 24 – Save the Date: BOOs & Brews on B Street

Cinemark Century San Mateo 12

320 2nd Ave.

• 3 Bees Coffee is offering 15% off when you spend $15 or more (Mention code DSMA)



• 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

• Cinemark Century San Mateo 12‘s BYOBucket returns on Sunday, September 6. Up to 400 oz. (2 XLs) of popcorn for only $5. No movie ticket required

• Foreigner Cafe has a Weekday Morning Special Monday-Friday 8-11am until December. Use promo code SAVEBIG8382 at checkout for 10% off

• Kiddo Adventure Indoor Playground has Hawaiian Style Shave Ice, and it’s open to the public

• Peninsula Italian American Social Club‘s Ristorante Italiano will begin serving dinner on Monday, September 7. A family-style buffet will be available from 5-8pm Monday-Friday. They also serve lunch Monday-Friday, 11:30am-2:30pm. Find more info here

• Porterhouse serves Prime Rib on Fridays and Saturdays, while it lasts

• Rise Woodfire will start serving weekend brunch this month, Saturdays and Sundays, 9am-2pm. The Grand Opening is September 26-27. Details here

• Congratulations, Sibby’s Cupcakery, on year 12 of winning the Gold Medal for Best Bakery for Birthday Cake or Cupcakes on the Peninsula! Thank you, Bay Area Parent magazine readers

• Welcome to the neighborhood: Hey Yogurt, Odd One Out Tea, SweatHouz

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)

• ABC7News – Viral Bay Area barber helping kids build confidence with classic cut (Full Circle Barbershop and “Beasty Cutz” Ritz Bautista)
• Hoodline – B Street Shuts Down for Free Motown and Top 40 Nights This September
• KQED – California Advocates Want Newsom to Fulfill Promise to Fund Childcare Spaces (Peninsula Family Service)
• Palo Alto Online – Italian restaurant Roma Antica is coming soon to downtown San Mateo
• San Mateo Daily Journal – More than morning drop-off: Celebrating the teachers who come first (Peninsula Family Service)
• San Mateo Daily Journal – Increasing age-friendly businesses
• San Mateo Daily Journal – The oldest home in San Mateo: A look inside the historic William Sands home — and the life of its steward