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December has arrived, and with it comes a flurry of festive fun in Bay Meadows and across the Peninsula. From twinkling tree lightings and hands-on holiday workshops to lively markets, community celebrations, and even Santa swooping in by helicopter, this month is packed with ways to savor the season. Whether you’re lacing up your skates at San Mateo on Ice, hunting for the perfect handmade gift, sharing a cozy brunch with Santa, or ringing in the New Year at noon, there’s something magical happening every week.

When you live just steps from Caltrain it’s easy to get from here to ‘there’ car-free! Get the Hillsdale Caltrain schedule here. Dive into our December lineup and discover all the ways to celebrate, create, explore, and connect this holiday season.

Bay Meadows Run Club with Basecamp San Mateo. Join this free fun run Wednesday evenings at 6pm 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 welcome. 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.

Sunday Downtown San Mateo Farmers Market. West Coast Farmer’s market is kicking off a new location at 222 East 4th Avenue Sundays from 9am to 2pm in Downtown San Mateo. The new farmer’s market will have a curated selection of fresh fruits, veggies, and a couple of tasty food trucks to fuel your morning stroll.

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.

Now – January 11, San Mateo on Ice. Located in Central Park, San Mateo, our 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.

December 1-21, Santa’s Saving You a Seat. Join Pinstripes at Hillsdale San Mateo for a delicious brunch you won’t forget. Snap selfies with the jolliest guy around, stack your plate and settle into the holiday spirit.

December 5, First Friday Nights. On the first Friday of every month, from 5 PM until 8 PM, parents and kids celebrate together at CuriOdyssey in San Mateo. Dance to some of your favorite hits, while enjoying animal presentations and science activities.

December 6, Winter Wonderland at Central Park. Celebrate the season in San Mateo at Central Park from 5:00–7:00 pm! This winter-themed event is perfect for the whole family, featuring holiday music, kids’ activities, crafts, festive photo opportunities, cookie decorating, hot chocolate, and more.

December 6, Clayroom San Mateo Holiday Market. Open to the public from 11am to 4pm on Saturday, Dec 6 visitors can explore handmade ceramics, unique gifts, and holiday creations from local artists in a festive, community-focused setting at Bay Meadows. Hop on Facebook and invite friends to brunch at The Breakfast Club – Midtown San Mateo followed by this San Mateo Clay Arts Holiday Market.

December 6-23, Firefighter’s Toys for Tots. Donate a toy to a child in need at the Hillsdale Shopping Center in San Mateo. Located in the South End near The LEGO Store.

December 6, Winter Wonderland Workshop.  Head to Belmont and enjoy a Winter Wonderland Workshop, where little elves ages 5-12 can craft sparkly ornaments, frost delicious cookies, write jolly letters to Santa, sip steamy hot cocoa, and so much more. It’s the coolest way to celebrate the season.

December 6, Santa Arrives by Helicopter. Move over Rudolph, Santa is arriving in his personal helicopter to Hiller Aviation in San Carlos! Enjoy Christmas Carols and Christmas wishes.

December 6, Winter Wonderland. Enjoy an enchanting winter evening filled with cookie decorating, bouncing on inflatables, and enjoying a cozy hot cocoa station in Redwood City.

December 6-7, Holiday Wreath Workshop. Use your imagination to create a one-of-a-kind beautiful wreath. They will provide a variety of fresh greens from San Mateo Central Park and all the supplies (frame, ribbon, wire & embellishments) you need to create your wreath.

December 6-7, The Samaritan House Giving Tree will collect donations at Macy’s Center Court from 2-7pm on December 6–7, and the San Mateo Consolidated Firefighters Toy Program will accept toy donations from December 6–23.

December 7 + 10 “Paws with Claus” photo sessions will be held every Sunday and Wednesday from 5–7 p.m.,  For animal lovers, the Peninsula Humane Society and SPCA will host a holiday adoption pop-up now through December 24, offering the perfect opportunity to bring a new furry family member home for the holidays.

December 8–19, Holiday Wreaths at Fioli. Celebrate the season in Woodside with a one-of-a-kind wreath-making experience set in the heart of the holidays. Learn the art of crafting a stunning wreath as you weave together fresh greens, dried accents, and festive flair.

December 11, Santa at the Belmont Firehouse & Toy Drive. Open to all ages and includes photos with Santa and beloved holiday characters, snow, hand-on holiday crafts, and refreshments. While this event is free, they kindly ask that you bring at least one new, unwrapped toy for a child in need this holiday season.

December 13, Caltrain Holiday Train – Get Your Tickets NOW! The Holiday Train will be making stops at Millbrae, San Mateo, Redwood City, Palo Alto, Mountain View, Santa Clara and San Jose Diridon Stations. A ticket for the Holiday Train works as a Day Pass, allowing riders to visit some of the many family events being held on December 13, including San Mateo on Ice, Redwood City’s Hometown Holidays, Mountain View’s German Night Market, Santa Clara’s South Bay Historical Railroad Society, and San Jose’s Christmas in the Park.

December 14 from 1-3PM, the Annual Dogly Sweater Contest is back at Fieldwork Brewing San Mateo! Don your ugliest sweater, twin with your dog, and get to the beer garden to enter the contest. A fun tradition in Bay Meadows’ dog-friendly neighborhood!

December 14, 16th Annual Chanukah Festival. Join the festive celebration at Courthouse Square in Redwood City with Menorah Lighting, live music, and delicious latkes & donuts—fun for the whole family.

December 18, Mele Kalikimaka Day at Fieldwork Brewing San Mateo! Dress in your favorite Hawaiian shirt, get to the beer garden at Bay Meadows to enjoy some Hawaiian pizza and the re-release of Coconut Milk Double IPA.

December 20, Fine Art Underglazing with Sheila Chen. Celebrate the season with a creative ceramics experience at Clayroom San Mateo at Bay Meadows. In this exclusive members only workshop, you’ll learn fine art painting techniques using underglaze to decorate a custom ceramic piece inspired by your favorite pet, or any subject that speaks to you.

December 21, Holiday Cookie Tray. In this Baking Arts in San Mateo class students will make an almond raspberry Linzer cookies and an assortment of Viennese hand-piped butter cookies, served dipped, sandwiched or sprinkled. This is from scratch baking at it’s best. Take your finished cookies home with you.

December 21, HEAD WEST Marketplace. Visit Downtown San Mateo’s South B Street every third Sunday of the month. Browse unique holiday gifts or find a treat for yourself from 50 local Makers, Merchants, Crafters, Designers, and Artists. While you’re here, explore over 100 of Downtown’s retail offerings, delicious dining destinations, and local art — there’s something for everyone this season.

Note to Hillsdale San Mateo shoppers, mall hours:

• Christmas Eve: 8am-5pm
• Christmas Day: Closed

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

November/December 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 timeslot. 6-week in-studio classes for pottery.

Bel Mateo Bowl Friday, Saturday and Sundays in San Mateo.
Karoake – Fridays from 7:30 – 11:30pm hit the mic with friends for some Karaoke.
Planet Bowling – Bowl in the dark under black lights on Fridays from 9:30 – 11:30pm and Saturdays from 8- 11:30pm.
Incredibowl – Fridays 9:30 – 11:30pm and Saturdays from 8 – 11:30pm interactive graphics elevate your bowling game with Incredibowl.
Family Pizza Night – Sundays from 5-8pm Family Pizza Nights and all you can bowl 8-10pm!
All You Can Bowl – Sundays enjoy unlimited bowling for 2 hours 8- 10pm!

Bicycle Sundays. From 9am – 3pm, 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 including jogging, bicycling, hiking, roller-skating, and walking. Cañada Road between Edgewood Road to the Filoli entrance will remain open to vehicles. 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.