October News and Events in Downtown San Mateo

Downtown San Mateo Association Community

News

OCTOBER 2025

“Boo”s and Brews in October

We had a busy September in our neighborhood: Movies in the Park, the San Mateo Firefighters’ Association’s Chili Cook Off, two September Nights on B Street, a Downtown Historic District Walking Tour, 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.

October brings more fun events Downtown, including Jazz on B Street, “Boo”s and Brews on B Street, and, of course, the Downtown San Mateo Farmers Market and HEAD WEST Marketplace.

Check out 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.

Our small business community appreciates your support.

“Boo”s and Brews on B Street

We’re teaming up with the City of San Mateo Parks and Recreation Department to present “Boo”s and Brews on B Street on Saturday, October 25, from 3-5pm on the Pedestrian Mall (B Street between 1st & 3rd Avenues).

Join us for a FREE, FANG-tastic event including kid-friendly activities, crafts, photo booth, music, and trick-or-treating. We encourage all to dress up in your Halloween costumes! NEW this year, Devil’s Canyon Brewing Co. will be selling beer and wine onsite with a percentage of the proceeds going to the Police Activities League.

We hope to see you for a SPOOK-tacular day!

**Event details may change due to inclement weather

Jazz on B Street

Join us for Jazz on B Street on Saturday, October 4, as we welcome Swingatto, a dynamic Swing and Gypsy jazz trio, to Downtown.

From 1-3pm, let their lively melodies transport you to another era while you enjoy a delightful afternoon in the heart of Downtown. Don’t miss this chance to experience music that’s as vibrant as our community.

**Event details may change due to inclement weather

Save the Date: Shop Small

Shop local, shop small! Head Downtown Downtown on Small Business Saturday, November 29, to support our small businesses.

We’ll feature performances from Melodic Outreach Endeavor (Aragon High School musicians) from 12-4:30pm.

Stay tuned for more information about Small Business Saturday.

HEAD WEST Marketplace

The monthly HEAD WEST Marketplace returns to B Street on Sunday, October 19. 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.

More Upcoming Events

October 2 – Music Bingo: General Song List (Chill Spot Rendezvous)
October 2 – An Evening of Remembrance (from Sutter Health)
October 3 – First Friday Dinner Dance (Peninsula Italian American Social Club)
October 3 – Latin Night Social Party (Motion Arts Center)(every Friday)
October 4 – Cinema & Chill (Chill Spot Rendezvous)(every Saturday)
October 4 – Jazz on B Street with Swingatto
October 4 – Heels Workshop (Motion Arts Center)
October 4 – Milonga Tango Party (Motion Arts Center)(every Saturday)
October 5 – Downtown San Mateo Farmers Market (every Sunday)
October 5 – Succulent Topped Pumpkin Workshop & Master Gardener Plant Clinic (San Mateo Arboretum Society)
October 5 – Karaoke (McGoverns)(every Sunday)
October 5 – Gratitude Meditation (Chill Spot Rendezvous)
October 6 – Swing Social (Motion Arts Center)
October 7 – Trivia Tuesdays (McGoverns)(every Tuesday)
October 9 – Harvest Happy Hour (San Mateo Public Library)
October 11 – San Mateo Consolidated Fire Open House
October 11 – Spooky Book Faire (San Mateo Public Library)
October 11 – Ladies Styling and Footwork Workshop (Motion Arts Center)
October 11 – Mixology 101 Class (Fogbird)
October 11 – Genovese Night (Peninsula Italian American Social Club)
October 14 – Music Bingo: Golden Oldies (Chill Spot Rendezvous)(2nd and 4th Tuesday)
October 18 – Tango Technique Workshop (Motion Arts Center)
October 19 – HEAD WEST Marketplace
October 25 – “Thriller” Dance Workshop (Motion Arts Center)
October 25 – Cocktail Masters Class: Advanced Mixology (Fogbird)
October 25 – Boos and Brews on B Street
October 25 – Halloween Party (San Mateo Public Library)
October 25 – Italian Heritage Night (Peninsula Italian American Social Club)
October 25 – Halloween Milonga Sentimental Tango Party (Motion Arts Center)
October 27 – Cooking Demonstration (Peninsula Italian American Social Club)
October 31 – Halloween Latin Night (Motion Arts Center)
November 14 – Save the Date: San Mateo on Ice opens
November 29 – Save the Date: Small Business Saturday

Downtown Business Updates

Peninsula Dance Academy,

717 S. B St.

Enjoy 20% off Amici’s BBQ Chicken Pizza & Caesar Salad this month. Offer valid on pick-up and delivery orders during the month of October only via their website or mobile app
Bodyrok has added classes: Mondays & Thursdays 2:30pm, Thursdays 3:30pm
Colander Kitchens is serving dinner Thursday-Sunday
Gao Viet Kitchen is now open later on Fridays-Saturdays: Kitchen open until 9:30pm, Bar open until 10pm
Manyak Dental Group has a monthly Saturday date. Call them to book a spot
Peninsula Dance Academy is accepting new students at their new Downtown location. They offer Ballet, Jazz, Contemporary, and Mommy and Me classes
Thonglor Thai Bistro is under new management
Wunderbar is taking a fall hiatus
Welcome to the neighborhood: Akiba HQ, EverBank, No.5 House

City of San Mateo Announcements

Climate Leadership

The City of San Mateo is committed to being a climate leader and reducing greenhouse gas emissions in our community. The development and adoption of amendments to the green building code, also known as “reach codes,” can help reduce emissions. The City of San Mateo is exploring these reach codes for the 2025 Code Cycle (2025-2027). The outreach schedule includes four dates (October 1, 8, and 23, November 3)

Age-Friendly Businesses Downtown

Congratulations to our newly certified Age-Friendly Businesses Downtown! We’re proud to recognize these local businesses for their commitment to accessibility, inclusivity, and excellent service for all generations. By taking steps to make their spaces more welcoming for older adults, they’re helping us build a more vibrant and age-friendly community for everyone. This page has more information about the program and the full list of certified businesses. Downtown businesses are: Baking Arts, Chill Spot Rendezvous, Footwear etc., Peninsula Family Service, Porterhouse, San Mateo Lock Works, Site for Sore Eyes

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)

Pedestrian Scrambles on B St.

New Pedestrian Scrambles are active at 1st & B St., 2nd and B St., and 3rd 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

Free Compost

San Mateo residents can pick up FREE compost at the Corporation Yard (1949 Pacific Blvd.) and Anchor Rd/Bay Trail Lot (Anchor Rd at 3rd Ave./J. Hart Clinton Dr.). Details here

Storm & Flood Preparedness

Find information about sandbags, and preparation and safety tips on our Storm & Flood Preparedness page

Daylighting Law and Red Curbs

To improve visibility and keep families safe, the City is adding red curbs near schools and crosswalks in line with California’s new Daylighting Law (AB 413). See more information here