Bay Meadows

Get ready to enjoy a full month of activities in the Bay Meadows neighborhood and beyond. We’ve rounded up an agenda full of festive holiday lights, handmade holiday soirees, wreath making, winter wonder and specialty workshops, ice skating, visits with Santa 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.

December 7, 11, 14, 18, 21, 25, 28, Bay Meadows Run Club with Basecamp San Mateo. Join this free fun run Wednesday evenings at 5:30pm and Saturday mornings at 8am. Meet at 3050 S. Delaware for a 2-, 3-, 4- or 6-mile loop (something for everyone) to get moving. Run, jog, or walk. Happening weekly – rain or shine. All paces and people are welcomed. Members often gather in Town Square for a Blue Bottle coffee or at Fieldwork Brewing Beer Garden after each run. Plus, there’s no fee! You heard right – membership is not required. This is a community building fun run, compliments of our neighbors at Basecamp Bay Meadows.

December 7, 14, 21, 28, College of San Mateo Farmers’ Market. Shop seasonally and fresh each Saturday from 9am to 1pm (year-round) at San Mateo’s largest farmer’s market located at 1700 West Hillsdale Boulevard. The best summer produce is joined with the first of the fall harvest. Get your stone fruit before it’s gone, and also enjoy apples, grapes, and winter squash! Seasonal Highlight: Acorn Squash.

November 25-December 1, “Shop Small” in San Mateo. It’s time to celebrate San Mateo and support local businesses! Make any purchase, whether from a retail store, restaurant, grocer, wellness provider, fitness facility, or any small business in the City of San Mateo for a chance to win incredible prizes.

December 1, Holiday Wreath Workshop. ​Use your imagination to create a one-of-a-kind beautiful wreath at the San Mateo Arboretum in San Mateo.

December 1, Zoppé Italian Family Circus. The Zoppe Italian Family Circus returns to Redwood City for the 17th year for spectacular two-hour performances that will enthrall the entire family.

December 2-24, Annual Holiday Toy Drive at Hillsdale. Partake in the San Mateo Consolidated Fire Department’s Annual Toy Drive for Children. Bring joy to disadvantaged kids with a NEW toy donation.

December 5, 12, 19, Thursday Night Lights. Mark your calendar for holiday carolers and extended shopping hours in San Carlos on selected Thursdays. Enjoy live entertainment and make this holiday season unforgettable by purchasing gifts from your favorite local shops.

December 6, First Friday. The San Mateo County History Museum in Redwood City will be open without admission fees the first Friday of every month as part of its continuing “FREE First Fridays” program.

December 6, Evening With The Dickens Fair. Immerse yourself in The Great Christmas Dickens Fair” with a sneak peek at the Hillsdale in San Mateo. Enjoy strolling Victorian characters, live musical performances and traditional holiday entertainment and craft making from a bygone era.

December 6, Night of Holiday Lights. Spread holiday cheer with friends and family downtown San Carlos. Enjoy games, treats, live performances, and best of all – snow.

December 7, Clayroom San Mateo Handmade Holiday Sale. Shop handmade from 30+ small batch artisans at the studio from 11am to 5pm! Browse a variety of unique, one-of-a-kind pieces, including pottery, sculptures, and decorative art. It’s the perfect opportunity to find beautiful, locally made gifts for everyone on your list this holiday season!

December 7, Winter Wonderland. Enjoy this indoor winter-themed event at Central Park for the whole family! Winter Wonderland features holiday music, crafts, photo opportunities, cookie decorating and hot chocolate in downtown San Mateo.

December 7, Weekend Workshop: Light it Up. Explore the magical world of lights and learn how they brighten our lives, from the sun’s rays to UV we can’t see. Through hands-on experiments and fun activities, you’ll discover how light travels, changes colors, and get a unique view on IlluminOdyssey in San Mateo.

December 7, Hometown Holidays. Get ready for a jolly day of festive fun in Redwood City. Downtown and Courthouse Square will be packed with fun for the whole family. Enjoy a spectacular parade, live entertainment, thrilling carnival rides, and a petting zoo.

December 7, Santa Arrives by Helicopter. Move over Rudolph, Santa is arriving in his personal helicopter! Join the Hiller Aviation Museum in San Carlos for Christmas Carols and Christmas wishes.

December 7, Winter Wonderland Workshop. Explore the enchantment of the season through creative arts and craft activities in Belmont. Participants will have the opportunity to design ornaments, decorate holiday cookies, write a letter to Santa, enjoy hot cocoa, and much more!

December 7 + 8, Caltrain Holiday Train.  December 7 & 8, the 2024 Holiday Train rings in the start of the holiday season. Santa and friends start their journey in San Francisco before heading south, stopping at stations along the Caltrain corridor – making a stop in San Mateo at 5:30pm!

December 9, Last Day: Letters to Santa. This holiday season, youth can write a letter to the North Pole and get a free personalized response in return from Santa and his elves (aka Belmont Parks & Recreation Dept).

Thru December 11, Santa Pet Nights. Bring your furry family members to visit with Santa at the Hillsdale Shopping Center in San Mateo on Sundays & Wednesdays from 5-7pm.

December 14, Breakfast with Santa. The SMC Fire Department invites you to the annual pancake breakfast with Santa at Downtown San Mateo Fire Dept. Station 21 (120 S. Ellsworth Ave.) Santa arrives at 9:30 AM—don’t miss your chance for photos on the iconic 1912 fire engine, thanks to Event Bros. Firefighters will be accepting donations of unwrapped toys to benefit the community.

December 14, Holiday Cookie Tray. Students at Baking Arts in San Mateo will make a almond raspberry linzer cookies and an assortment of Viennese hand-piped butter cookies, served dipped, sandwiched and sprinkled.

December 14, Winter Wonderland. Enjoy an enchanting winter evening in Redwood City filled with cookie decorating, bouncing on inflatables, and enjoying a cozy hot cocoa station.

December 20, Silicon Valley Ice Skating Association. Enjoy an unforgettable evening of grace, skill, and inspiration at the Silicon Valley Ice Skating Association’s Charity Gala on San Mateo On Ice.

December 21, Fieldwork Brewing San Mateo Dogly Sweater Contest. WIN PRIZES! Dress to impress in your ugliest holiday sweater with your pup and enjoy a festive afternoon filled with holiday cheer, card & ornament decorating, hot cocoa for the kids, and of course lots of fresh beer (not for the kids). Join friends and neighbors from 1-3pm.

December 21, Chocolate Babka. Students at Baking Arts in San Mateo will make our tender, buttery brioche dough from scratch and our deliciously fudge-y chocolate filling.

December 21-22, Nutcracker at San Mateo Performing Arts Center. Join the Stahlbaum children on a heartwarming adventure on Christmas Eve as Fräulein Drosselmeyer brings to life a cast of delightful characters and entrancing tales from a very magical book.

December 22, HEAD WEST Marketplace. Visit Downtown San Mateo’s B Street and browse unique holiday gifts or find a treat for yourself from 50 local Makers, Merchants, Crafters, Designers, and Artists.

Thru December 22, Gingerbread House Workshop. Enjoy a Gingerbread House and Cookie Decorating Workshops at the Hillsdale Shopping Center in San Mateo with all sweet trimming included.

Thru December 24, Photos With Santa. Kids can share their must-have wish list and smile for the camera to capture the moment with Santa and enjoy Santa’s wonderland with interactive displays and games and view the magical décor and indoor tree with lights all aglow at the Hillsdale Shopping Center in San Mateo.

Thru December 24, Adopt a Furry Friend. Pet Adoptions Hosted by SPCA | PHS at the Hillsdale Shopping Center Nordstrom Court in San Mateo.

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

Thru January 12, San Mateo on Ice. Located in Central Park, 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. San Mateo on Ice offers daily recreational ice skating, parties, private ice time and special event bookings.

January/February Sessions at Clayroom. When signing up for 6-week classes, one signs up by selecting (signing up for) the 1st class. Classes 2-6 will occur on a weekly cadence during the same day of the week and time-slot. 6-week in-studio classes for pottery.

Trivia Night: Every other Monday at Hillsdale. Gather your pals every other Monday from 6-8pm for Trivia Night hosted by Sandcastle Entertainment! Fantastic food, beer and fun at The Refuge.

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. Check for holiday closures.

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.