Events and Community Programs

San Mateo On Ice Returns November 15-January 12

The Ice-Skating Rink in Central Park is a San Mateo tradition everyone loves.  Experience the sheer joy of swirling and twirling on the glistening ice as you create unforgettable memories with family and friends. Whether you’re a seasoned skater or a beginner, the state-of-the-art rink offers a welcoming atmosphere, top-notch ice conditions, and a delightful ambiance to make your skating adventure truly magical.

• Ice skates are included with admission!

• Tickets begin at $18, or $33 with a Skate Buddy (if you are a novice or out-of-practice skater)

HEAD WEST Holiday Markets – November 24 and December 22, 11am-4pm

The Holiday season is HERE! Visit Downtown San Mateo's B Street for HEAD WEST Marketplace on Sunday, November 24, and Sunday, December 22! Browse unique holiday gifts or find a treat for yourself from 50 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 this season!

Shop Small To Win Big! November 25-December 1

It’s time to celebrate San Mateo and support local businesses! Small Business Saturday, November 30th, 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.

You already 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...and the entire week around it!

Step 1: To have a chance to win a prize, Shop Small in San Mateo between November 25th and December 1st, 2024! Make any purchase, whether from a retail store, restaurant, grocer, wellness provider, fitness facility, or any small business in the City of San Mateo.

Step 2: Fill out the form, including a photo of your proof of purchase, by December 3rd at noon PT. Make sure the name of the business and address are visible on the receipt! 1 entry per person.

Step 3: The San Mateo Area Chamber of Commerce and DSMA will randomly draw winners from qualifying participants! Prizes include gift certificates from Porterhouse, Cuban Kitchen, Elements Massage, Christian & Rafferty Fine Jewelry and more. Winners will be notified by email.

The deadline for entries is December 3rd at noon PT. Winners will be randomly selected after entries have been verified. Winners will be notified via email and prizes can be mailed or picked up in person.

Holiday Train Celebration December 7th

The 2024 Caltrain Holiday Train rings in the start of the holiday season in San Mateo!

Santa and friends start their journey in San Francisco before heading south, stopping at stations along the Caltrain corridor. The Holiday Train is scheduled to stop at the San Mateo Downtown Station on Saturday, December 7th at 5:30pm and depart at 5:50pm.  There will be music, games for the kids and plenty of hot chocolate.  Please come out to be part of this great tradition!