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November brings a festive spirit to the Peninsula as autumn gives way to the holiday season. From outdoor ice skating and seasonal shopping at Hillsdale Mall (just next door) to cultural celebrations, live entertainment, and family-friendly activities, there are plenty of ways to make the most of the month close to Bay Meadows.

Get into the holiday spirit at San Mateo on Ice, discover unique gifts at local artisan markets, explore seasonal flavors at neighborhood farmers markets, or enjoy a creative workshop with friends. Whether you’re embracing the first signs of the holidays, planning a family outing, or simply enjoying the vibrant community around you, November offers plenty of opportunities to celebrate, connect, and explore San Mateo and beyond.

When you live just steps from Caltrain, getting from here to there is easy and car-free. Grab the Hillsdale Caltrain schedule and dive into our monthly event roundup to discover all the ways to celebrate, create, explore, and connect throughout the month ahead.

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 runs year-round at 222 East 4th Avenue Sundays from 9am to 2pm in Downtown San Mateo. The farmer’s market has 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.

November 1, Nightfall at Filoli. Explore glowing woodlands, pumpkins, firelight, mysterious clues, and an enchanted mansion during this immersive after-dark Halloween experience at Filoli in Woodside.

November 1, Straw Rocket Workshop. Blast off into a hands-on adventure at Hiller Aviation Museum in San Carlos, where kids can explore rocket science and create their own rocket-inspired projects using everyday craft materials.

November 1, From Ordinary to Extraordinary Holiday Designs. Get inspired for the holidays at the San Mateo Arboretum Society with a free floral design demonstration by Greg Lum, featuring tips for creating beautiful seasonal arrangements, plus a raffle for finished designs.

November 1, Knit, Etc. at the Library. Bring your knitting, crochet, or other stitching projects to the San Mateo Main Library for a relaxed afternoon of creativity, conversation, and community. All experience levels are welcome.

November 6, Repair Advice Workshop with Fixit Clinic. Give your favorite household items a second life at this hands-on repair workshop at the Burlingame Public Library, where you can get advice on fixing everyday belongings instead of replacing them.

November 6, First Friday Nights. On the first Friday of every month, from 5–8 PM, parents and kids celebrate together at CuriOdyssey in San Mateo with an evening of family-friendly discovery and fun.

November 8, Brunch & Burn at Pinstripes. Start your day with an energizing yoga session followed by a delicious brunch at Pinstripes in Hillsdale Shopping Center in San Mateo. A perfect way to combine wellness, relaxation, and a little weekend indulgence.

November 8, Día de los Muertos Celebration. Celebrate the traditions of Día de los Muertos at Courthouse Square in Redwood City with a colorful cultural gathering honoring loved ones and the heritage of Latin America.

November 8, Helicopter Adventure. Discover the science of vertical flight at Hiller Aviation Museum in San Carlos, where kids can build and fly paper helicopters, explore aircraft design, and climb inside a real helicopter cockpit.

November 8, Magical Music & Motion. Enjoy a family-friendly performance featuring Woodside Cheer as part of Redwood City’s community events lineup.

November 9, AI for Everyday Life. Discover practical ways to use artificial intelligence for everyday tasks, creative projects, and simplifying your routine during this informative presentation at the San Mateo Main Library.

November 11, Pizza Making Class at Pinstripes. Roll up your sleeves and discover the art of pizza making during a hands-on class at Pinstripes in Hillsdale Shopping Center in San Mateo.

November 13, San Mateo on Ice Holiday Tree Lighting & Opening Celebration. Celebrate the start of the holiday season with a festive tree lighting and figure skating performances at Central Park in San Mateo.

November 13, Once Upon a Vase: Audiobook Night & Paint. Settle in with your favorite audiobook while painting pottery, enjoying snacks, and connecting with fellow book lovers at Color Me Mine in Downtown San Mateo.

November 13, Starlight Nights. Explore the wonders of the night sky at Hiller Aviation Museum in San Carlos with indoor planetarium-style sky shows and, weather permitting, telescope views of the Moon and planets.

November 13–January 10, San Mateo on Ice. Lace up your skates and celebrate the holiday season at San Mateo’s outdoor ice rink in Central Park, where families and friends can enjoy skating during the day or under the stars.

November 14, Kids Club at Pinstripes. Bring the little ones to Pinstripes at Hillsdale Shopping Center in San Mateo for a fun-filled, family-friendly experience featuring activities designed just for kids.

November 14, Science Fun Fest. Explore the fun side of science during this community event in Redwood City, offering an opportunity for curious minds to discover and learn.

November 14, Neave Trio. Enjoy an afternoon of chamber music with the Grammy-nominated Neave Trio at the San Mateo Main Library, featuring a musical conversation with the acclaimed ensemble.

November 14, Mixology 101: Classic Cocktails. Shake, stir, and sip your way through a hands-on cocktail-making class at Fogbird in Downtown San Mateo, where expert bartenders will guide you through the art of crafting classic drinks.

November 19–December 20, School of Rock. Enjoy a high-energy theatrical production of School of Rock at Hillbarn Theatre in Foster City, featuring music, comedy, and a feel-good story.

November 20, Marsh Hike at Coyote Point. Discover the beauty of San Mateo’s coastal wetlands during a free guided hike with CuriOdyssey educators, exploring native plants, wildlife, and seasonal changes along Coyote Point’s marsh trails.

November 21, ART on the Square: 11th Annual Holiday Show. Get a head start on holiday shopping at the San Mateo County History Museum in Redwood City, where more than 25 local artists will showcase handcrafted gifts and one-of-a-kind creations beneath the museum’s stunning stained-glass dome.

November 21, HEAD WEST Marketplace. Spend the day exploring Downtown San Mateo’s B Street, shopping handcrafted goods from local makers, artists, and designers while enjoying the neighborhood’s restaurants and boutiques.

November 22, Line Tracing Robots. Explore the exciting world of robotics and introductory coding during a hands-on educational activity at Hiller Aviation Museum in San Carlos.

November 25, Turkey Toss! Get ready for some Thanksgiving-themed fun at Hiller Aviation Museum in San Carlos during this playful event inspired by the classic WKRP in Cincinnati television episode.

November 28, Free Art Project at Magical Bridge Playground. Bring the kids for a creative afternoon of art and community fun at Magical Bridge Playground in Redwood City’s Red Morton Park.

Recurring:

Every Tuesday, Discount Tuesdays at Cinemark. Make movie night a midweek tradition with discounted tickets at Cinemark Century San Mateo 12 in Downtown San Mateo.

Nov/Dec 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.