Fill Your Stocking with December Events

Looking for some fun this December? Dig into our local list of events and fill your calendar with holiday cheer including an ugly sweater party, nutcracker performances, ice skating, the Holiday Train, festive parades, family-friendly shenanigans, and lots more!

Enjoy free admission at the History Museum in Redwood City on the first Friday of every month on December 1.

Take a spin on the ice San Mateo on Ice through January 15. The outdoor ice rink features 9,000 square feet of REAL ice. Skaters will be able to skate in the sunshine during the day, and under the stars at night.

The Holiday Train returns to San Mateo Dec 3 at 6pm! The Caltrain Holiday Train presented by Silicon Valley Community Foundation, a Bay Area tradition since 2001, is a free family event that brings together thousands of local community members in the spirit of joy and giving. Visitors are invited to see the glittering Holiday Train at one of its station stops, enjoy the entertainment and bring new, unwrapped toys to donate to local, under-served kids. The event will benefit the U.S. Marine Corps Reserve Toys for Tots and The Salvation Army’s Season of Giving Program to help local families.

Give a gift at the Samaritan House Holiday Toy Drive in San Mateo. Donate a new, unwrapped toy and bring a smile to a child. December 1- 30.  Or donate at Hillsdale Shopping Center (Lego Level). Dec 8-23 new and used toys will be collected by the San Mateo Fire Department. Your donations will be distributed to local children just in time for the holidays.

Catch Holly Days near Macy’s Center Court at Hillsdale Dec 7, 8 and 9. Kids will enjoy decorating sugar cookies and festive, winter craft making.

Join Gingerbread House Decorating Party Dec 9! Just $25 per house. Up to 2 children per house. Parent/Guardian can assist at no charge. Reservations required. Activity appropriate for ages 3 and up

Bring Fido. Capture the Purrr-fect Photo at Santa Pet Nights – offered Weds and Sundays through Dec 13 at Hillsdale Shopping Center!

Head to Central Park in San Mateo on December 1-2 for Winter Wonderland 2017, featuring cookie decorating, snow, music, arts, crafts and more.

Redwood City’s annual “Hometown Holidays” event at the San Mateo Courthouse Square includes a festive parade, live entertainment, music performances, a visit from Santa, real falling snow and more! December 2.

Join the Watercolor Japanese Teacups and Stationary class at SweetBloomsCo in San Mateo. You will get 4-6 cards plus envelopes. A beautiful curated box with all the materials you need to keep practicing at home. December 2.

A Holiday photo with Santa is on everyone’s list! Capture a photo to be treasured for years with a variety of keepsake packages at Hillsdale Shopping Center next to Bay Meadows until Dec 24.

Peninsula Ballet Theatre’s Nutcracker Sweet in San Mateo is the perfect length holiday ballet for families with toddlers, preschoolers, and anyone who is excited to see the “Greatest Hits!” of Nutcracker. December 2, 3, 9, 10. You can also attend the Sugar Plum Tea Party and meet the Sugar Plum Fairy, Clara and all of their friends on December 2 and 10.

Do you like to paint, eat good food, and meet new people? Head to Open Paint by CATA at Cyclismo Café in downtown Redwood City on December 7.

One of San Francisco’s longest-running pop-up restaurants is coming to Burlingame to create this event with authentic Puerto Rican food, drinks and music. Join the Holiday Party at Leland Tea on December 8.

Put on your favorite Ugly Sweater and enjoy an evening of fun with dancing, drinking, and donating at Club Fox’s Ugly Sweater Party on December 9 in Redwood City. All proceeds will be donated to helping the victims of the North Bay Wildfires.

Join the Noon Year’s Eve Celebration on December 31! Celebrate the New Year with music, activities, face painting and a countdown balloon drop at noon at the Hiller Aviation Museum in San Carlos.

Step back in time and celebrate the New Year on December 31 at Scroll Bar & Kitchen’s Great Gatsby New Year’s Eve Party in Redwood City.

Experience Midurban life. Bay Meadows is a family-friendly neighborhood with lots of open space to enjoy all year long. Whether it’s growing your own vegetables in a gorgeous community garden with expert guidance, playing a game of pick-up basketball after work, team building over bocce, picnicking with family on warm summer nights or getting fit with pop-up fitness and yoga classes curated just for you, there’s no shortage of green space to explore. If you have little ones, don’t miss Momdays on Mondays in Paddock Park! Check out life out and about at Bay Meadows by following us on Instagram.