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Downtown San Mateo Association Community
News
DECEMBER 2025
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Celebrate a Cheery December Downtown
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November marked the start of the holidays Downtown. San Mateo on Ice returned to Central Park, we celebrated small businesses with Shop Small to Win Big, and live music on Small Business Saturday. And our monthly HEAD WEST Marketplace and weekly Downtown San Mateo Farmers Market added to the fun.
December will bring Sounds of the Season, Santa Mateo 2025, Winter Wonderland, Gala d’Oro, the Holiday Train, Las Posadas on North B Street, the final HEAD WEST Marketplace of the year, and a whole month of ice skating at San Mateo on Ice.
Just a reminder that DSMA.org has great resources, such as our Events Calendar, Restaurant Guide, Deals and Promotions page, a Walking Tour, and an archive of our past newsletters.
We know you already love and support the local businesses of San Mateo! That’s why the San Mateo Area Chamber of Commerce and the Downtown San Mateo Association (DSMA) want to thank you for “shopping small” on Small Business Saturday. Continue to support our small business community by shopping at San Mateo small businesses through Friday, December 12, and then entering Shop Small to Win Big. The deadline for entries is noon on Saturday, December 13. Participate for your chance to win prizes from Avenida, Clawesome, Elements Massage, Fanloli Beauty, Golden Moon Gallery, Porterhouse, Sports Basement, Susan European Beauty Therapy, and more. See all the details here.
Follow us on Facebook and Instagram to see videos featuring San Mateo small businesses.
Thank you for your support of our small business community!
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Enjoy this indoor winter-themed event for the whole family featuring holiday music, crafts, festive photo opportunities, cookie decorating, hot chocolate, and more!
Winter Wonderland will be held at Central Park and the Recreation Center on Saturday, December 6, from 5-7pm.
More information here.
Changes and modifications of activities at this event may occur due to inclement weather.
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Don’t miss the unique holiday sounds of Business Casual, the national champion a cappella vocal band known for their smart and surprising genre-swapped covers.
Catch their performance on B Street on Saturday, December 6, from 5-6pm.
The performance is part of a festive evening downtown, coinciding with Santa Mateo 2025, a fun community event where 200 Santas will be running through the area!
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On Saturday, December 13, ticket holders will be able to ride the Caltrain Holiday Train Holiday Train for the first time! They’ll enjoy a beautifully decorated interior, carols, a reading of holiday stories, arts and crafts, and even a visit from Santa. The Holiday Train will be making a total of eight stops in each direction.
Prior to the arrival of the Holiday Train, families can enjoy free entertainment at station stops at San Francisco, San Mateo, Palo Alto, and San Jose Diridon Stations. These station events are open to the public and will be the only stations where ticket holders are allowed to board the Holiday Train.
Featured in Downtown San Mateo: Core Taekwondo, Peninsula Dance Academy, and Hillsdale High School Chamber Singers.
The Northbound train will depart the Downtown station at 3:30pm, and the Southbound train will depart at 5:13pm.
See more information regarding tickets and the schedule here.
The Holiday Train is no longer a toy drive. Please do not bring toys to the Holiday Train.
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The final date of HEAD WEST Marketplace in 2025 is here! If you’ve been meaning to stop by and check out the incredible vendors, don’t delay. Your next chance is Sunday, December 21, from 11am-4pm.
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.
This HEAD WEST will be extra special, with a visit from Santa between noon and 3pm! Sponsored by Izzo Therapy, Santa will walk through the marketplace, posing for selfies and collecting wish lists from kids young and old.
HEAD WEST is always FREE. All are welcome, and it’s pet and kid-friendly. Plus: Live music!
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Downtown Business Updates
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- In December, enjoy 15% off gift cards at Amici’s. Offer valid in stores and online through Tuesday, December 23.
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Anton SV Patisserie offers several easy pick-up and delivery options, including pick up from over 40 locations across the Bay Area, same-day delivery, and Saturday delivery to more than 30 Bay Area cities
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Assistance League’s Turnstyle Shop is normally open Tuesday, Friday, and Saturday, but this month, they will be open Thursday, December 18, and Monday, December 22. Then they will be closed from December 25- January 1, opening again on Friday, January 2
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- Enjoy Happy Hour at Espetus Monday-Friday, 5-7pm
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Porterhouse is open for lunch Tuesday-Friday, 11:30am-2pm, December 2-19
- Celebrate Happy Hour at Taishoken Friday-Sunday 3-6pm
- Spend $30 at Tang Bar during lunch hours and get a $3 off voucher, through Monday, December 15
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City of San Mateo Announcements
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Storm & Flood Preparedness
Sandbag stations are now open! Find information about sandbags, and preparation and safety tips on the City’s Storm & Flood Preparedness page
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
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). Find more information here
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Downtown San Mateo in the News
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Downtown San Mateo Association
Phone: (650) 342-5520
HQ@dsma.org
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