Bay Meadows

December brings a month of holiday cheer into the Bay Meadows neighborhood and just beyond. Make it a merry month with events that include Santa arriving by helicopter, the San Mateo holiday train, a Santa PJ party, ice skating, s’mores and hot beverages, plus cookie decorating classes, wreath workshops, and much, much more. When you live just steps from Caltrain it’s easy to get from here to ‘there’ car-free! Get the Hillsdale Caltrain schedule here. Explore our roundup and plan your month.

Intro to Clay 2023. Start your month off with a Beginner 6 Week Intro to Wheel Throwing at ClayRoom in San Mateo at Bay Meadows. A great starting place for an intense 6-week course where students are introduced to throwing on the wheel, trimming work, surface design techniques, glazing, and a week of hand-building that can be used to incorporate into wheelwork or on its own.

Thru January 7, San Mateo on Ice. Located in Central Park, the San Mateo on Ice outdoor rink features 11,000 square feet of real ice making it the largest outdoor ice rink in the Bay Area. Upcoming FREE community skate days include Dec 5 and 12 thanks to generous sponsors. The rink is open daily through Jan 7!

Thru January 7, Holidays at Filoli in Woodside. ‘Tis the season to make special memories, bask in the vibrant landscape, and spend time together. Step into the magic of the House decked in Holiday cheer and explore the winter Garden, where inspiration glows. Santa flies in on select Santa Days in December. Snap a photo with him on his magical golden throne and enjoy a daytime stroll through the winter blooms.

Thru January 28, Four Seasons Silicon Valley Après Village. Simulating a cozy mountainside retreat with mini-chalets and a synthetic skate rink, the seasonal pop-up features a festive village like no other in the Bay Area for the whole family to experience. This year, Après Village & Skate Rink welcomes a delectable addition – an innovative food truck for patrons to enjoy. The Après alpine-inspired menu is made complete with house-made signature s’mores and hot beverages.

Thru Dec 23, Cut Your Own Tree at Santa’s Tree Farm. The farm will send you off with a saw to select your perfect Douglas, Noble or Concolor Fir, or Redwood. Founded in 1972, Santa’s Tree Farm and Village in Half Moon Bay, CA, is a 487-acre Choose-and-Cut Christmas tree farm with 4 different kinds of trees growing right here on the farm.

Each weekend thru Dec 16 from 10am to 6pm, The Great Dickens’ Christmas Fair returns to the Cow Palace in Daly City!  Discover holiday revelry in this lamp-lit city brimming with hundreds of lively and colorful characters from the imagination of Charles Dickens.

December 1-24, Santa Photos. Capture the magic of the season with photos with Santa at Hillsdale in San Mateo. Catch Santa Pet Night’s on Sunday’s & Wednesdays at Macy’s Center Court.

December 1-23, Gingerbread House Workshop. Kathy’s Creative Kakes will be hosting Gingerbread House Decorating every Monday – Sunday in upper-level Nordstrom Court at Hillsdale in San Mateo.

December 1, First Friday Nights. Your winter light experience just got a glow-up! On the first Friday of every month parents and kids celebrate together at CuriOdyssey in San Mateo.

December 2, 6, 9, 13,16, 20, 23, 27 Bay Meadows Run Club. Hit the 3 mile loop at Bay Meadows with your neighbors Wednesday evenings and Saturday mornings. This weekly event welcomes all people at all levels (walkers included). Generously launched, led and organized by our newest retailers at Basecamp San Mateo, the group often gathers in Town Square for a Blue Bottle coffee or at Fieldwork Brewing after each run.

December 2, Build-A-Bear Teddy Bear Drive. Make a furry friend for only $12 and donate it to The At Risk Youth Foundation at Hillsdale in San Mateo.

December 2, Santa Arrives by Helicopter. Move over Rudolph. Santa is arriving in his personal helicopter at the Hiller in San Carlos.

December 2, Walking in a Winter Wonderland in Central Park. Enjoy this indoor winter-themed event for the whole family in San Mateo. Winter Wonderland features holiday music, crafts, photo opportunities, cookie decorating and hot chocolate.

December 2, Hometown Holidays 2023. Get ready to jingle all the way in Redwood City. Enjoy an epic parade, exciting live entertainment, heart-pounding carnival rides, and Santa Claus himself.

December 2, 9, 16 and 23, Shop Saturdays at College of San Mateo Farmers’ Market. Peruse seasonal finds every Saturday from 9am to 1pm (year-round) at San Mateo’s largest farmer’s market located at 1700 West Hillsdale Boulevard. Bring a big shopping bag or two because the farmers’ tables are filled apples, grapes, leafy greens, and winter squash. Watch for pomegranates this month!

December 3, Clayroom San Mateo Opening Party.  Sunday, Dec 3 is the opening party for Clayroom SF at Bay Meadows! Pop over to 3050 S. Delaware Street (Survey Monkey Building) between 4-7pm to check out the gorgeous, new San Mateo ceramics art space, watch live demos, learn about classes/membership and win prizes!

December 3, Caltrain Holiday Train San Mateo Stop. During the 20-minute station stops, Santa, Mrs. Claus, Frosty and the gang will get off the train to greet children and spread holiday cheer. The dazzling show train, with more than 70,000 glittering lights.

December 3, Santa PJ Party. Put on your comfiest pajamas and get ready for a morning of holiday cheer as you join the Hillsdale Shopping Center for a rise-and-shine Santa PJ Party.

December 6, Create a Bay Meadows Cookie Exchange. Plan your first annual cookie exchange with a few neighbors. Start small and build on something special that someday the whole neighborhood can get involved. Follow these steps and you’ll enjoy a perfect party with friends, food, festive cheer, and enough sweets to last you the rest of the season.

December 9, Santa’s Workshop. Join the elves at Santa’s Workshop in Belmont for a memorable time creating festive themed crafts and treats to share with your family and friends this holiday season.

December 9, Pause, Sip, and Explore. Purchase tickets early to reserve your spot at the final tasting of the year – ideal for selecting holiday wines for your soirees! Kick off the holiday season with a fun, informative, and social wine tasting in San Mateo.

December 10, Bot Bowl. Join the Robo Bowl in San Carlos and take a turn commanding programmable robots to run plays in the Hiller Aviation Museum’s own robotic stadium.

December 10, 14th Annual Chanukah Festival. The Menorah is created by 27 different pre-painted canvases. Enjoy Menorah lighting, moon bounces, latkes & donuts in Redwood City.

December 12, Candle Lighting and Hanukkah Celebration. Head to Foster City for a community candle lighting and gathering with donuts, dreidels, music, latkes, gelt, balloons, and more.

December 16, Winter Wonderland. Enjoy an enchanting winter evening filled with cookie decorating, winter crafts, inflatables, a hot cocoa station, candy cane hunt, and photos with Santa in Redwood City.

December 16, Nature Hike. Join Friends of Edgewood on a free guided hike to discover the sights and sounds of the season at Edgewood Park and Natural Preserve in Redwood City.

December 17, Succulent Wreath Making Workshop. Craft up a beautiful treasure during this succulent wreath-making workshop in San Mateo while enjoying a complimentary tea or coffee.

December 20, Royal Icing Cookie Decorating. This royal icing cookie decorating class in San Mateo covers all the necessary fundamentals you will need to recreate the cookies you seen in magazines and social media.

December 27, Grapes and Giggles Holiday Comedy Show. See comedians featured on late-night TV, Comedy Central, SF Sketchfest, Bay Area Festivals and more in San Carlos.

December 29, Kids’ Carnival. Aircraft checkouts, cockpit exploration, glider and helicopter construction and more are just some of the activities available at the Hiller Aviation Museum in San Carlos.

December 31, Noon Year’s Eve. Kids and parents, come celebrate the New Year at the Hiller in San Carlos with music, activities, face painting and a countdown to THREE GIANT balloon drops at noon.

Bicycle Sundays. A 3.8-mile segment of Cañada Road along Crystal Springs Regional Trail is closed between the Filoli entrance and Highway 92 allowing for non-motorized activities.

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 an organic community garden, playing a game of pick-up basketball after work, team building over bocce in the beer garden, picnicking with family on warm summer nights or with a run around the park, there’s no shortage of green space to explore. Check out life out and about at Bay Meadows by following us on Instagram