Play
Bay Meadows October Agenda
Get ready for Día de los Muertos, Diwali, pumpkin festivals, goblin walks, boo bashes, haunted hangars, and all the autumn menu flavors in the Bay Meadows neighborhood and beyond.
Pick up an orange cream NOLA and some chocolate chip pumpkin pound cake at the Blue Bottle Cafe in Town Square or hit the Fieldwork Brewing San Mateo Beer Garden and catch a game on the jumbotron with your favorite craft brews. Host a gathering with your favorite Halloween flicks! When it’s time to adventure around the Peninsula, it’s easy to get from here to ‘there’ car-free! Get the Hillsdale Caltrain schedule here. Explore our curated agenda, explore, and plan a month bursting with festivities.
There’s still time to create your own community event and celebrate tradition on the block at Bay Meadows – find a few ideas here.
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.
Tuesday 25th Avenue San Mateo Farmers’ Market. Back through October 21 on Tuesdays from 3pm to 7 pm, this farmers market is an easy walk or bike ride from Bay Meadows (~0.8 mi), bringing the best Peninsula produce and makers moments from your door.
Wednesday Foster City Night Market by Off The Grid 5 to 9 pm through October. Ride your bikes from Bay Meadows to the Foster City Lagoon for a fun time! Running each Weds weekly through October 2025, just adjacent to Bay Meadows San Mateo in nearby Foster City, Off The Grid is bringing live entertainment and delicious mobile food options to the beautiful Leo Ryan Park meadow! Pet and family friendly with live entertainment.
Saturday 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.
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.
Filoli Nightfall. Don’t miss your only chance to experience the Trolls by moonlight in Woodside October 3 – November 10. Nightfall™ returns for its 2nd annual takeover—bigger, bolder, and more enchantingly eerie than ever before! As twilight descends, Filoli transforms into a mysterious world of roaming slugs, glowing mushrooms, shifting shadows, and spooky scarecrows.
This year’s U-Pick Sunflower season at Andreotti Family Farm in Half Moon Bay is NOW OPEN and runs November 23. Find out more HERE.
Fall into Science during the month of October at CuriOdyssey in San Mateo. Explore carnivorous plants, the bone zone, ghostly illusions and more!
Woodside Performing Arts Center presents showings of THE WEDDING SINGER, a musical comedy on select dates Oct 3 – Oct 12! Big hair, electric guitars and laugh out loud fun for ages 13+.
October 2, Fieldwork Brewing San Mateo’s 49ers Tailgate Pizza Night with Neapolitan pies made to order and the game on the jumbotron in the Bay Meadows Beer Garden. Starts at 5:15pm.
October 3, Rock the Block Finale at Pinstripes. Enjoy an unforgettable night of live music, food, drinks, and fun as Pinstripes San Mateo hosts its Rock the Block Finale, inspired by Hillsdale Mall’s popular concert series.
October 3, Movies in the Park. Movies begin at sundown at Barrett Community Center in Belmont, showing ‘Shrek’. Your favorite movie snacks will be for sale at the snack bar.
October 3, Free First Friday at San Mateo County History Museum 10am to 4pm. San Mateo County History Museum continues its “FREE First Fridays” with FREE museum admission all day from 10am to 4pm.
October 4, NAMIWALKS San Mateo County. Features a 1k and 5k walk along beautiful SF Bay, music, food, a community resource fair, wellness programming, a kids’ zone, and for the first time – a pet contest.
October 5, Succulent Topped Pumpkin Workshop. San Mateo Arboretum volunteers will show you how to make a unique decoration to celebrate the Fall Season.
October 8, Buttercream Flower Cupcakes. An introductory class in San Mateo on buttercream piping flowers, blossoms and leaves. Take your finished cupcakes home with you at the end of class along with recipes.
October 9- Nov 2, Hillbarn Theatre in Foster City presents ‘Murder for Two’ – a madcap musical comedy that blends murder mystery with vaudevillian flair.
October 11, Dia de los Muertos. Head to Dr. Martin Luther King Jr. Park in San Mateo to honor Día de los Muertos with a vibrant celebration of life and tradition. Stay tuned for more details coming soon!
October 11-12, Art & Wine Faire. Don’t miss the Peninsula’s favorite Fall celebration in San Carlos. Gather with friends and family to enjoy 200+ artists, beer and wine, food, and entertainment on three stages!
October 12, Sugar Skull Workshop at San Mateo County History Museum in Redwood City. Prepare for Día de los Muertos (Day of the Dead) as you learn how to make calaveras de dulce (sugar skulls) in a Hands-On History workshop led by Elizabeth McCarthy.
October 13, Safeway World Championship Pumpkin Weigh-Off join others in the picturesque “World Pumpkin Capital” of Half Moon Bay, California, this legendary contest—dubbed the “Super Bowl of Weigh-Offs”—draws the world’s premier pumpkin growers eager to claim glory and possibly squash the world record with colossal, Volkswagen-sized orange behemoths.
October 18, Fosterberfest in Foster City, a brand-new fall festival in Foster City filled with fun, flavor, and community spirit!
October 18, Chocolate Fest of Belmont. Enjoy an elegant celebration of all things chocolate at Silicon Valley’s favorite annual chocolate event and fundraiser for San Mateo County Health Foundation!
October 18, A Motherpuppin’ Howl O Ween Treat Bar 9am to 1pm at Parkside Aquatic Park, San Mateo. $10 per treat station or so all 3 for $22 Plus free photo ops!
October 18, Meetup to Make Art in the Park at Central Park (or Hillsdale if raining) with the San Mateo 20s 30s Meetup Group.
October 18-19, Half Moon Bay Art and Pumpkin Festival. The world-famous festival is the season’s signature event, drawing hordes of visitors to the “World Pumpkin Capital” for an epic festival on historic Main Street.
October 18-19 Filoli Taste of Fall. Celebrate the season with a tasting event filled with fall flavors, local vendors, and festive ambiance. Stroll through a vibrant marketplace of artisans in the Woodland Court, where you can taste ciders and signature cocktails, diverse seasonal dishes, and fall inspired desserts.
October 18-27, Halloween Haunted Hangar. Visit the Hiller Aviation Museum in San Carlos this October for a frightful treat! Come in costume and see the Gallery decked out in its spooky Halloween decorations and the “Great Pumpkin” Scavenger Hunt.
October 19, Diwali Celebration. The Belmont Library and the City of Belmont are curating a colorful event, filled with music, dance, crafts, and more! Free and open to all ages.
October 19, 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. Runs through December.
October 24, Goblin Walk. It’s the spookiest time of the year, when the tiniest ghouls and ghosts haunt Downtown San Carlos in search of candy!
October 25, Boos on B Street. Get ready for a spooktacular time at Boos on B Street in San Mateo! The fun will take over B Street between 1st and 3rd Avenue – more details coming soon!
October 26, DOGGOWEEN is BACK at Fieldwork Brewing San Mateo. Sunday 10/26 from 1-3pm, bring your costumed doggo to the Bay Meadows Beer Garden for tail wags and terrifyingly good times. To enter your dog in the costume contest and be considered for the grand prize you must: sign-in at the taproom, dog must be present & in costume and participate in the costume parade. Winners (by popular vote) will be given Fieldwork gift cards!
October 26, Snap a Photo with Jack Skellington at Hillsdale Shopping Center on North Block Plaza from 1-3pm.
October 26, Scary Music From the Movies – Halloween Concert – Redwood Symphony in Redwood City. At 3pm, the Cañada College Main Theater will be transformed into a haunted hall as Maestro Eric Kujawsky leads our ghoulishly attired musicians in a program of spooky favorites.
October 29, Health Fair at the College of San Mateo. Community members are welcome to attend and enjoy wellness-related resources from 40+ exhibitors, free flu shots, food, and give aways.
October 29, Belmont Boo Bash. This event is free and open to all ages and includes a Trunk or Treat, haunted buildings throughout Twin Pines Park, live music, and delicious bites from local food trucks.
October 31, Show us your Bay Meadows spirit! Tag @baymeadowslife in your Reels, Photos and Stories. We want to see your jack-o-lanterns, stoop decor, costumes (include those canines) and more! We’ll be sharing our favorites.
Thru November, Rock the Dock Concert Series in Redwood City. Enjoy live music, dancing, food and fun on the waterfront. Concert-goers should bring lawn chairs, blankets, jackets and refreshments. On-site food vendors will also be available.
September/October 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!
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.