October News and Events in Downtown San Mateo



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Downtown San Mateo Association Community

News

OCTOBER 2026

 
 

October Downtown: Boos and Brews & More

We love seeing Downtown San Mateo so vibrant! Thank you to everyone who came out in September for a Movie in the Park, September Nights on B Street, HEAD WEST, and the Arts & Culture Fest. The fun continues all through October with Boos & Brews on B Street, HEAD WEST, and an extension of Dine & Discover through Sunday, October 25. It is the perfect excuse to gather with friends, try a new restaurant, and score local prizes.

Follow our Facebook and Instagram pages to catch all the latest news, or head over to DSMA.org. 

Boos and Brews on B Street

Spend an afternoon Downtown at Boos and Brews on B Street. trick-or-treating, listening to music, eating and drinking delicious food and drinks, and enjoying festive fun for the whole family.

Join us on Saturday, October 24, from 3-5pm on the Pedestrian Mall on B Street between 1st and 3rd Avenues. Activities include:

  • Trick-or-treating
  • Arts and Crafts 
  • Reptile Petting Zoo
  • Music
  • Food and Drinks
  • Photo Opportunities

Grab lunch first and head on over, or enjoy the event and then grab dinner. Costumes are welcomed and highly encouraged! 

This event is run by the City of San Mateo Parks and Recreation Department and the DSMA and will be SPOOK-tacular.

HEAD WEST Marketplace

HEAD WEST Marketplace returns to B Street on Saturday, October 17, 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

logo for Dine & Discover with illustration of buildings and trees

Dine & Discover Extended!

Dine & Discover Downtown San Mateo has been extended through Sunday, October 25. 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

Find details here.

*Terms and conditions may apply

Unlock Everything Downtown San Mateo Has to Offer

From hidden gem eateries to major street festivals, DSMA.org is built to help you get the absolute most out of our neighborhood. Here is a taste of what you’ll find on the site:

  • Browse our Events Calendar for upcoming comedy shows, karaoke nights, live music, and community events
  • Use our Restaurant Guide to find top-rated dining, drinks, and sweet treats
  • Check out exclusive deals and promotions from your favorite Downtown shops
  • Take a self-guided Historic Walking Tour next time you are out for a stroll

 

More Upcoming Events

Downtown Business Updates

Takahashi Market, c. 1930s

221 S. Claremont St.

  • 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

  • Anatolian Market has updated hours: Monday 8am-3pm, Tuesday- Saturday 8am-7pm, Sunday 8am-6pm

  • Baking Arts & Coffee has redesigned the booking experience so you can manage your registration with ease. For classes booked through the new site, you can reschedule, change, or cancel your booking (10+ days in advance) by clicking “Manage My Bookings” on the classes page or find the link in your confirmation email. No account required and no booking fees. (They’re also offering a Gluten-Free Salted Caramel Whipped Cream Roll Cake class, and one of the favorite recipes from their teen camps is now available for adults: Cinnamon Rolls.) 

  • Blue Moon Bar has added Bar Bingo to its schedule (Tuesday, 6-8pm)

  • Nakoko has new hours: Monday, Wednesday, Thursday 12:30-7pm, Friday 12:30-8pm, Saturday-Sunday 11am-8pm, Tuesday closed

  • Pausa‘s new bar menu is available until 6pm in the bar area and outside, and is also available all day for guests dining at the bar

  • Rise Woodfire is serving weekend brunch, Saturdays and Sundays, 9:30am-2pm

  • Tai Er has new Lunch Specials, available Monday–Friday, 11:30am-2:30pm: Combo for One $25: A main dish + veggie dish + rice; Combo for Two $55: A shareable spread of Sichuan favourites, veggies + rice for two

City of San Mateo Announcements

Main Street Garage Construction

Please be advised that construction work at the Main Street Garage is scheduled to take place from October 2026 through February 2027.

 

The construction project includes improvements to the garage’s waterproofing system to protect the structural integrity of the facility, prevent water intrusion and deterioration, and extend the useful life of the garage.

 

During the construction period:

  • Businesses will remain open throughout the project. The City encourages customers to continue supporting and visiting local businesses as usual
  • The elevator will remain operational throughout the construction period, providing continued access to all levels of the garage
  • The top level of the parking garage will be closed for approximately three weeks during the construction period. The exact dates of this closure will be announced once they are confirmed

 

The City of San Mateo appreciates your patience and understanding as this work is completed. Thank you for continuing to support the businesses in the area throughout the construction project.

Downtown Pedestrian Mall: Making Crossings Safer

To support the community’s safe use of the pedestrian scrambles at First, Second, and Third Avenues and South B Street, and to reduce driver frustration, The City has made several recent changes:

  • New signs: New signs were installed above the pedestrian signals and push buttons at the First, Second and Third Avenue intersections to make it easier to notice and understand when to cross. Pedestrians should cross when they see the “walk” sign, while green lights are for vehicles
  • Signal timing change at Third Avenue: The order of the traffic signal was changed so pedestrians get to cross before drivers on B Street get their green light. The goal is to reinforce that pedestrians should wait for their turn to cross
  • Talking crosswalk signal at Third Avenue: The crosswalk signal at Third Avenue and B Street now talks. When it’s time to walk, it announces “walk sign is on for all crossings.” If you push the button and it’s not yet your turn, it will remind you to wait periodically. This will be watched to see how well this works before deciding whether to add it at other crossings nearby
  • Extended crosswalk striping: Public Works crews extended the crosswalk lines fully through the First, Second and Third Avenue intersections. This helps further clarify that the public can cross in any direction, including diagonally, through the intersection



The City is planning additional pavement markings within the intersections to further help guide pedestrians safely across. Staff will also continue to monitor the intersections to evaluate the success of these changes and the need for additional improvements. Thanks for your patience and feedback as work is done to make Downtown safer for everyone.

Storm & Flood Preparedness

With the rainy season approaching, now is the time to prepare your home and property for storms and potential flooding. Taking a few simple steps before wet weather arrives can help protect your property and keep our community safe.

The City of San Mateo’s self-service sandbag stations will open 24/7 starting Thursday, October 1. Sandbags will be available to San Mateo residents and property owners, with a limit of 10 bags per vehicle. Residents should bring their own shovel and gloves. Sand and bags will be provided while supplies last and will be refilled throughout the rainy season.

Self-service sandbag stations will be available at three locations:

  • City of San Mateo Corporation Yard
  • Beresford Park
  • Anchor Road/Bay Trail

Before the rain arrives, take a few minutes to prepare. Review storm and flood preparedness resources and find your nearest sandbag location.

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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