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Enjoy Festive Fun Downtown in November

October was so much fun Downtown! We had Jazz on B Street, “Boo”s and Brews on B Street, and, of course, the weekly Downtown San Mateo Farmers Market and monthly HEAD WEST Marketplace.

November means festive fun Downtown. San Mateo on Ice returns to Central Park, we’re celebrating small businesses with Shop Small to Win Big, and live music on Small Business Saturday. And, of course, don’t miss HEAD WEST Marketplace, and the Downtown San Mateo Farmers Market.

Check out our Events Calendar, Restaurant Guide, Deals and Promotions page, and a Walking Tour on DSMA.org. There’s also an archive of our past newsletters.

We always appreciate your support of our small business community.

Follow us on Facebook and Instagram so that you find out about last-minute updates and events, as well as reviews of neighborhood businesses, secrets of our town, historic photos, and round-ups of upcoming weekend events.

San Mateo on Ice

San Mateo on Ice returns to Central Park on Friday, November 14!

San Mateo on Ice offers daily recreational ice skating, parties, private ice time, and special event bookings.

Located on Fitzgerald Field, the outdoor ice rink features 11,000 square feet of REAL ice. Skaters will be able to skate in the sunshine during the day or under the stars at night.

See the calendar here.

Tickets must be purchased online.

The rink will be open until Sunday, January 11, 2026.

Sounds of the Season

While you’re Downtown supporting our small businesses on Small Business Saturday, November 29, get into the holiday spirit with Sounds of the Season.

Melodic Outreach Endeavor (musicians from Aragon High School) will be playing for shoppers on B Street from 12-4:30pm.

Shop Small to Win Big

It’s time to celebrate San Mateo and support local businesses!

Small Business Saturday is a day dedicated to supporting small businesses and communities across the country, and is part of the larger Shop Small Movement. Founded by American Express in 2010, this day is celebrated each year on the Saturday after Thanksgiving in the U.S. 

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” this Small Business Saturday.

See details here.

Follow us on Facebook and Instagram to see videos featuring San Mateo small businesses.

HEAD WEST Marketplace

There are only two more installments of HEAD WEST Marketplace in 2025! If you’ve been meaning to stop by and check out the incredible vendors, don’t delay! Your next chance is Sunday, November 16, 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.

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.

• November 1 – Cinema & Chill (Chill Spot Rendezvous)(every Saturday)
• November 1 – The Amelia Vollers House: An 1891 Queen Anne Victorian in San Mateo (Main Library)
• November 1 – Milonga Tango Party (Motion Arts Center)(every Saturday)
• November 2 – Downtown San Mateo Farmers Market (every Sunday)
• November 2 – Gratitude Meditation (Chill Spot Rendezvous)
• November 2 – Rain Water Harvesting and Rain Gardens & Master Gardener Plant Clinic (San Mateo Arboretum Society)
• November 2 – Karaoke (McGoverns)(every Sunday)
• November 3 – Sound Healing (Tree of Life Healing Center for the Soul)
• November 3 – Final Outreach Meeting for Reach Codes (City Hall)
• November 3 – Swing Social (Motion Arts Center)
• November 4 – Trivia Tuesdays (McGoverns)(every Tuesday)
• November 7 – Latin Night Social Party (Motion Arts Center)(every Friday)
• November 7 – First Friday Dinner Dance (Peninsula Italian American Social Club)
• November 7 – Music Bingo: General Song List (Chill Spot Rendezvous)
• November 8 – Meet Author Maxwell Kim (Main Library)
• November 9 – 101st Airborne Packing & Letter Writing Day (San Mateo Elks Lodge)
• November 14 – San Mateo on Ice opens
• November 15 – Trio Bohemo (Main Library)
• November 15 – Cocktail Masters Class (Fogbird)
• November 15 – Sicilian Night (Peninsula Italian American Social Club)
• November 16 – HEAD WEST Marketplace
• November 29 – Small Business Saturday
• December 6 – Save the Date: Winter Wonderland

Police Appreciation Day

at the Vendome,

415 2nd Ave.

• Each month, enjoy 20% off specials at Amici’s. This month’s specials are Detroit Style SMOG Pizza and Kale & Sausage Pasta. Offer valid on pick-up and delivery orders during the month of November only via their website or mobile app

• Anton SV Patisserie offers curated catering sets of delicious breakfast pastries and coffee for office meetings

• B Street & Vine is open 11:30am-9pm Tuesday-Wednesday, and 11:30am-midnight (kitchen closes at 10pm) Thursday-Saturday

• Celebrate Happy Hour with BOGO 25% off at Chill Spot Rendezvous from 4-6pm

• Congratulations to Diane Christensen of Christensen & Rafferty Fine Jewelry on her retirement after 50 years in the jewelry business!

• Cognition Cyclery is now San Mateo Cycle Sport

• Curry Pizza House has deals on pints and small plates during Happy Hour

• In October, LifeMoves held a Police Appreciation Day BBQ to thank the officers of the Downtown Unit for supporting the Vendome and other homeless outreach efforts

• Enjoy 10% off for MY Dumpling‘s anniversary

• Celebrate Aloha Hour/Happy Hour at Pacific Catch Monday-Friday 3-6pm, Saturday-Sunday 3-5pm, and Wine Tuesdays (bottles 50% off all day)

• Peninsula Dance Academy is offering Postnatal Mommy & Me classes every Wednesday 10-11am

• Tang Bar has a special lunch promo running through mid-December. Get $3 off your next visit when you spend $30 during lunch hours Monday-Friday. (Ask staff for a voucher)

• tinyB chocolate now has gelato

• Tokie’s has new hours: Tuesday-Thursday 5-9pm, Friday-Saturday 5-9:30pm, Sunday 4-8:30pm, closed Monday

• Tomatina has a new menu

• Welcome to the neighborhood: Clawesome, El Camino Ballet, Lucent Pilates, Tree of Life Healing Center for the Soul

New Garden Space in Central Park

The San Mateo Arboretum Society partnered with students from Centennial Montessori School to create a new garden space in Central Park. Designed to be dog-friendly and highlight the importance of native plants, the garden offers visitors and their four-legged companions a peaceful place to enjoy the beauty of nature in the middle of our Downtown

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

Sandbag stations are now open! Find information about sandbags, and preparation and safety tips on the City’s 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

• Patch – New Bay Area Sichuan Restaurant Wants To Offer Guests An Authentic Dining Experience (Tai Er)
• San Mateo Daily Journal – ‘Clawcades’ coming to downtown San Mateo (Clawesome, Nakoko)
• San Mateo Daily Journal – Tai Er brings Sichuan flavors to San Mateo
• SFGate – Restaurant that sells 20 million bowls of its specialty debuts in the Bay Area (Tai Er)