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Enjoy Fall Downtown in September

August was so much fun Downtown: The Downtown Express returned for its second year, and there was HEAD WEST Marketplace, a Downtown Historic Walking Tour, live music with Reyna y su Trio, an Edgar Allan Poe Speakeasy, and the Downtown San Mateo Farmers Market. And Central Park was a busy place to be with the Central Park Music Series, and Central Bark.

September will be even busier: Special events include Movies in the Park, the San Mateo Firefighters’ Association’s Chili Cook Off, September Nights on B Street, the Autumn Moon Festival, the September Arts & Culture Fest, and regular events like the weekly Downtown San Mateo Farmers Market and our monthly HEAD WEST Marketplace.

You can always find our Events Calendar, Restaurant Guide, Deals and Promotions page, and a Walking Tour on DSMA.org. We’ve also added an archive of our past newsletters.

Thank you for supporting our small business community.

Be sure to follow us on Facebook and Instagram so that you don’t miss out on any of our great Downtown events.

September Nights on B Street

Family fun returns to B Street! Grab take-out from a local restaurant and enjoy outdoor dining Downtown on the pedestrian mall between 1st and 2nd Avenues. The street will be transformed into an outdoor dining pavilion with communal tables and chairs.

A children’s play area will be offered, and there will be live music for fun-loving attendees of all ages. Beer and wine will be available for purchase.

• Thursday, September 11 – 6pm to 8pm – Live music by Piano Madness (Singalong, Classics)

• Thursday, September 18 – 6pm to 8pm – Live music by Bud E. Luv (Swing / Big Band)

September Arts & Culture Fest

Head Downtown on Sunday, September 28, from 11am-5pm, for the September Arts & Culture Fest. Brought to you by the San Mateo Area Chamber of Commerce, the San Mateo County Office of Arts and Culture, and the Downtown San Mateo Association, you do not want to miss the local art, cultural performances, live music, kids activities, and more! 

Learn more here.

Chili Cook Off

The SMC Firefighters Annual Chili Cook Off is back! Bring your chairs, blankets, and appetite to Central Park on Satuday, September 6, 11am-4pm.

• Live music by Six50Productions
• Craft beer by Matagrano Inc.
• $15 entry gets you chili tastings, a full bowl, and a drink ticket
• Kids’ jump house, and more

Let’s turn up the heat for a good cause — all benefiting Muscular Dystrophy Association Northern California and the Tunnel to Towers Foundation.

HEAD WEST Marketplace

The monthly HEAD WEST Marketplace returns to B Street on Sunday, September 21. Held on the third Sunday of every month through December, from 11am-5pm, it’s a great event.

Shop small with amazing local makers, merchants, crafters, designers, and artists. From plants and stained glass, to vintage clothing and artisanal tea — there’s something for everyone.

HEAD WEST is always FREE. All are welcome, and it’s pet and kid-friendly. Plus: Live music!

Apply here to be part of the Marketplace.

• September 2 – Trivia Tuesdays (McGoverns) (every Tuesday)
• September 4 – Music Bingo: General Song List (Chill Spot Rendezvous)
• September 5 – Movies in the Park: Shrek (Central Park)
• September 5 – First Friday Dinner Dance (Peninsula Italian American Social Club)
• September 5 – Latin Night Social Party (Motion Arts Center) (every Friday)
• September 6 – San Mateo Firefighters’ Association’s Chili Cook Off (Central Park)
• September 6 – Cinema & Chill (Chill Spot Rendezvous) (every Saturday)
• September 6 – Mixology 101: Classic Cocktails (Fogbird)
• September 6 – Milonga Tango Party (Motion Arts Center) (every Saturday)
• September 6 – Live Music: Stone Temple Parents (McGoverns)
• September 7 – Downtown San Mateo Farmers Market (every Sunday)
• September 7 – Begonias – Perfect for the San Mateo Climate / Master Gardener Plant Clinic (San Mateo Arboretum Society)
• September 7 – Gratitude Meditation (Chill Spot Rendezvous)
• September 7 – Karaoke (McGoverns) (every Sunday)
• September 8 – Paws for Tales (Main Library)
• September 8 – Swing Social (Motion Arts Center)
• September 9 – Music Bingo: Golden Oldies (Chill Spot Rendezvous) (2nd and 4th Tuesday)
• September 11 – September Nights on B Street
• September 13 – Toscana Night (Peninsula Italian American Social Club)
• September 17 – Kevin Blake, Magician Extraordinaire (Peninsula Italian American Social Club) [RSVP by September 4]
• September 18 – September Nights on B Street
• September 19 – Stogies ‘n Steaks (Peninsula Italian American Social Club)
• September 20 – Advanced Mixology: Cocktail Masters Class (Fogbird)
• September 20 – Autumn Moon Festival (Central Park)
• September 20 – Veggie Gardening: Fall Beginnings and Summer Endings (Main Library)
• September 21 – HEAD WEST Marketplace
• September 22 – Bloodmobile Drive (Main Library)
• September 22 – Cooking Demonstration Night (Peninsula Italian American Social Club)
• September 25 – Author Talk: Jordan Steven Sher, Dark Shadow Hover (Main Library)
• September 28 – September Arts & Culture Fest
• October 25 – Save the Date: Boos on B Street

• Enjoy 20% off Amici’s Calabria Pizza and Honey & Garlic Wings in September. Offer valid on pick-up and delivery orders during the month of September only via their website or mobile app
• Anton SV Patisserie has new hours: Monday-Thursday 12-7pm, Friday-Saturday 11am-9pm, Sunday 11am-8pm
• Avenida has a new summer menu
• Come C Interiors has new hours: Friday-Monday 11am-5pm
• Espetus has live music on Friday and Saturday nights
• Motion Arts Center adds new classes every month. Check out their schedule here
• Congratulations, Pausa, on receiving a 2025 Michelin Bib Gourmand!
• Welcome to the neighborhood: Beem, Colander Kitchens

• From Monday, September 8, through Friday, September 11, the City’s contractor will be installing a new underground sewer line for the playground’s new restroom between East 5th Ave. and 9th Ave., causing temporary road closures of El Camino Real. Work may occur during daytime or nighttime hours and will be completed as quickly as possible. Please use caution while in the area, stay focused, and abide by all posted signage. The City has a webpage with updated information
• Reminder: Parking is FREE Downtown on Sundays and after 6pm every day. Find more information here (and please remember that this does not apply to private parking lots)
• Reminder: There are new Pedestrian Scrambles at 1st Ave. & B St., 2nd Ave. and B St., and 3rd Ave. and B St. A pedestrian scramble temporarily stops all vehicular traffic, and allows pedestrians to cross an intersection in every direction, including diagonally, at the same time
• San Mateo is offering FREE compost at the Corporation Yard (1949 Pacific Blvd.) and Anchor Rd/Bay Trail Lot (Anchor Rd at 3rd Ave./J. Hart Clinton Dr.). Self-service—bring your own shovel & containers. Details here
• The City is rolling out red curb marking in support of California’s new Daylighting Law (AB 413). Painting work is starting this summer near schools to help keep kids and families safe. Red curbs will be added near crosswalks to improve visibility and prevent blocked sightlines. Starting January 1, 2025, parking became prohibited within 20 feet of unmarked and marked crosswalks (or 15 feet with curb extensions), even if no red curb is present. See more information here

• The Good Trade – 7 Sustainable Futons & Sleeper Sofas for Small Spaces (2025) (The Futon Shop)
• KQED Food – Check Please! Bay Area (Rise Woodfire)
• Patch – New Sichuan Restaurant Opening Soon in San Mateo County (Tai Er)
• The San Francisco Peninsula Magazine – Issue 1 (Avenida, Backhaus, Fogbird, Jeffrey’s, Kajiken, Nandi Yoga, Ox9 Lanzhou Hand Pulled Noodles, Pacific Catch, Pausa, Porterhouse, Sibby’s Cupcakery, Sushi Yoshizumi, Taishoken, Wunderbar)
• San Mateo Daily Journal – Late night San Mateo shines
• NBC Bay Area California Live! – Layers of Love: Crafting the Perfect Crepe Cake (Anton SV Patisserie)