The Bay Meadows October Agenda

October comes whooshing into the Bay Meadows neighborhood with autumn colors and flavors! Sip cider, join a spooky scavenger hunt, savor some fall menu items in Town Square, enjoy a fun run, hop on a carnival ride, and much, much more at Bay Meadows and beyond. 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.

Create your own community-wide event in time for Halloween with these fun ideas! 

October 1, Succulent Topped Pumpkins. Learn to make unique decorations to celebrate the fall season. These fantasy pumpkins, aka Cinderella, last a lot longer than a traditional carving pumpkin.

October 1-29, Orchard Days in Woodside. Enjoy the bounty of fall in Filoli’s Gentleman’s Orchard, where the jewel-tones of autumn surround live music, spiced cider, and good times spent together.

October 2, This fall is all about the flow at Bay Meadows. The first round of Clayroom San Mateo classes are now live! Visit the website to register, as spots are limited! Clayroom San Mateo, a new community pottery studio in the Bay Meadows neighborhood. The ~ 4,000 sq. ft. open-plan studio, located in STA 4 at Bay Meadows  will be an outlet for all to learn, share and explore the medium of ceramics. Offerings consist of short/long format classes, memberships, kids programming and community events/outreach.

October 3, 10, 17, and 24: Catch the final month of the 25th Avenue San Mateo Farmers Market Tuesdays 3-7pm running through October 24th 2023. Greet the growers and peruse the autumn greens, gourds, winter squash, and root veggies to apples, grapes, and pears. Find prepared foods, baked goods, and more, too!

October 4, Sukkot Fun at Filoli. Celebrate Sukkot in the beautiful Filoli Orchard. Shake the lulav and etrog, sing, dance, and learn about the holiday while making new friends.

October 5, International Golf Scramble. The 2023 tournament will be held at the beautiful and sunny Crystal Springs Golf Course in Burlingame, with awe-inspiring scenery along the 20-mile Crystal Springs Reservoir.

October 6, First Friday Nights. Swing into the weekend with music, science, animals and fun! On the first Friday of every month parents and kids celebrate together at CuriOdyssey in San Mateo.

October 6, Movies in the Parks. Head to Barrett Park in Belmont for an evening of movies under the stars.

October 7, San Carlos Art & Wine Faire. This much-anticipated fall festival offers two full days of enjoyment for people of all ages, including a variety of children’s activities and live entertainment each day in San Carlos.

October 7, Port Fest. This annual event welcomes the community to learn about Redwood City’s maritime heritage and the history of our industrial working waterfront.

October 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. Potatoes are here! Bring a big shopping bag or two because the farmers’ tables are filled with the last of summer’s peaches and berries. Apples, grapes, leafy greens, and winter squash are also coming in fast!

October 8, VR Haunted House Zombie Adventure and Lunch. Immerse yourself in an action adventure with a group of friends after lunching at Cheesecake Factory at Hillsdale Shopping Center in San Mateo. After lunch, at Sandbox VR in San Mateo, you’ll team up in groups of up to 6 people, gearing up in full VR equipment to take part in the Deadwood Mansion adventure.

October 8, Chocolate Swiss Roll. In this fully hands on class at Baking Arts in San Mateo, every participant will make their own bittersweet chocolate Swiss roll cake from scratch.

October 13, Bair Island Walking Tour. Join Peninsula Open Space Trust for a walking tour at Bair Island in Redwood City and dive into the history of this beautiful protected space.

October 14,  Celebrate Dia de los Muertos in San Mateo on Saturday from 12-4pm in the Dr. Martin Luther King Jr. Community Park. From vendors to crafts to a car show and performances, bring your family and friends and enjoy a day in the sun!

October 14, Belmont Water Dog Run. The Belmont Water Dog Run, now in its 6th year, is growing into an anticipated annual community event.

October 20-21, Chocolate Fest of Belmont. Enjoy an elegant celebration of all things chocolate at Silicon Valley’s favorite annual chocolate event in Belmont.

October 21, 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.

October 21, Halloween Spooktacular. Step right up for some cool carnival games, muah-ah-ah monster maze, creepy crafts, spooky photo back drops, mini pumpkin patch, prizes & fun in Redwood City.

October 21, Halloween Bar Crawl @ San Mateo! In its 6th year, this spooktacular costumed bar crawl is happening in San Mateo at6-7pm: O’Neill’s, 7:15-8:15: Eddie’s, 8:30-9:30: Sky Lounge/3rd Ave. Sports Bar and 9:45-10:45+: McGoverns.

October 21, Breast Cancer Awareness Ride. This ride is a powerful opportunity to support the cause and raise awareness. Join Cycle Bar at Hillsdale Shopping Center in San Mateo for an inspiring session.

October 21-22 + 28-29, Halloween Haunted Hangar. Come in costume and see the Gallery decked out in its spooky Halloween decorations and the “Great Pumpkin” Scavenger Hunt at the Hiller in San Carlos.

October 27, RSVP in advance for this Open House at Clayroom San Mateo – NOW OPEN at Bay Meadows!  Have you ever wanted to create your own pottery or get into wood working? The spot to hone your craft is coming to your front doors at Bay Meadows and prospective members are invited to this preview open house from 6-8pm!

October 27, Trunk or Treat. Enjoy treats at Twin Pines Park in Belmont.

October 28 + 29: Hip Hop Halloween. A thrilling hip hop dance show full of chilling performances danced by your favorite classic spooky characters; Frankenstein, The Werewolf, The Mummy and More! Directed by Artistic Director Stuck Sanders and Alee Martinez at Peninsula Lively Arts in San Mateo.

October 28, Halloween Family Fun Night. The annual Halloween Family Fun Night at Highlands Rec Center in San Mateo is back on Friday, October 28th, running from 6:30 pm to 8:30 pm. It’s time to dust off your costumes and prepare for a night of thrilling activities.

October 28, Boos on B Street. Show off those costumes from 2-5pm in Downtown San Mateo on the Pedestrian Mall (B Street between 1st and 3rd Avenue) and enjoy carnival games, activities for the kids, crafts, and trick or treat through the Downtown San Mateo businesses!

October 28, Kids Art Classes at Magical Bridge Playground. Classes will take place in the Kindness Corner in Redwood City and will be available on a first come first served basis.

October 28, Monster Orchid Sale. 7 orchid vendors plus member sales at our one day sale in San Mateo.

October 28, Oddities & Curiosities Expo. You’ll find items such as: taxidermy, preserved specimens, original artwork, horror/Halloween inspired pieces, antiques, handcrafted oddities, quack medical devices, creepy clothing, odd jewelry, skulls/bones, funeral collectibles & much more at the San Mateo Event Center.

October 29, Doggoween Costume Contest at Fieldwork Brewing San Mateo, Bay Meadows! Sign ups begin at 12pm, parade begins at 12:30pm, judges will announce the winner at 1:30pm. Judging is based on popular vote so bring along your pups cheer section. Prizes include $50, $25 and $10 FWB gift cards.

October 29, Halloween Open Glass Terrarium. Celebrate Halloween with in San Mateo and create the scariest mini living world.

October 31, City HALLoween. Join Belmont City staff for a one-of-a-kind family friendly event at City Hall.

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.