The October Event Round-up

Fall in love with the new season this month! Pack your month with Halloween haunts, harvest festivals, Oktoberfest fun 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.

October 2, 9, 16, 23, 30, Off the Grid: Foster City. Live entertainment and food trucks return to Leo Ryan Park every Wednesday night.

October 2, Paint Like Frida Kahlo. Learn how to paint like Frida in this hands-on workshop in Foster City.

October 3, Bay Meadows’ Twilight Tails monthly event has been cancelled due to lack of attendance and participation. PLEASE NOTE: There will be no Howl O Ween Howl this year. 

October 4, Unhaunted Halloween First Friday. Dance and play in the moonlight at CuriOdyssey’s hauntingly fun October First Friday Family Night!

October 4, Free First Friday. Explore the History Museum in Redwood City, play in the past + a General Tour.

October 5, Bair Island Walking Tour. Tucked away right near Redwood City is Bair Island, a 3,000-acre mosaic of tidal channels, mudflats, and salt marsh vegetation.

October 5, 10th Annual PortFest. PortFest is a day-long waterfront festival held at Port of Redwood City.

October 5, PHS/SPCA Mobile Pet Adoptions. First Saturday of the month @ 12-2pm at Hillsdale in San Mateo.

October 5, Silicon Valley Walk to Defeat ALS. Walk for a cause at Coyote Point Recreation Area in San Mateo.

October 6, 13, 20, 27, (Final Month – Show your support!) Farmers Market Bay Meadows. Shop the market, enjoy live music, catch kids activities at Sweet Peas Tent hosted by Little Wonders San Mateo, plus park your pooch at the #PoochPitStop hosted by our friends at For Sniffs and Giggles! Every Sunday on the corner of E. 31st and Delaware Streets in San Mateo from 9:30am – 1:30pm (Rain or Shine).

October 6, Tapas y Platos. Experience innovative food prepared by Kitchentown chefs and ceramic pieces by artists from across the country.

October 10, Sunset Market at Bay Meadows. One Night Only. Gather after work for a game of ping pong under the stars, catch the food trucks on Derby Avenue, greet the growers and visit the beer garden for your Town Square favorites – your neighborhood farmers’ market is popping up at sunset one night only this season! Click here to invite friends and see who’s rolling in: 

October 11, Peninsula Ballet Theatre presents Cabaret: Hot October Nights. Enjoy an evening of dance, drinks and tapas!

October 12-13, San Carlos Art & Wine Faire. Taking place in the heart of downtown San Carlos, this much-anticipated fall festival offers two full days of enjoyment for people of all ages.

October 12, Peninsula Oktoberfest. Oktoberfest is at hand! The Hiller Aviation Museum joins the celebration with a special Oktoberfest beer, music and dining event.

October 12, Water Dog Run. This run takes runners and walkers through the streets of Belmont.

October 12, Whole Foods We Love Local In-Store Tasting Event. Meet the makers and people behind some of our favorite local brands and products.

October 13, 2019 Wursthall Oktoberfest. Enjoy a German-style buffet including Wursthall housemade bier bratwursts, rotating sausages from our Sausage Lab, pretzel bites, spaetzle, potato salad, and slaw.

October 17, Yoga+Beer (Costume Edition). Come ready to sweat, laugh, dance, breathe, stretch, drink, play, and socialize at Devil’s Canyon Brewing in San Carlos.

October 18, Silent Disco with LIFT Exercise San Mateo at Bay Meadows!
LIFT is taking bikes 🚲 and music 🎵 outside under the ✨! Oct 18th from 7:00pm to 9:00pm. Book your bikes online…event listed in the regular class schedule. @liftbbbsm @liftwitherinwetzel

October 19-20, Half Moon Bay Art & Pumpkin Festival. Spend the day in Half Moon Bay! Spy giant pumpkins, pumpkin carving, art & craft booths, entertainment, wine, beer, food vendors, and a parade.

October 20, Pumpkin Run/Walk. The 5K and 10K Run events take participants on the Coastal Trail along the bluffs overlooking the Pacific Ocean.

October 26, Haunted Hangar Party. Join ghosts, skeletons, witches and warlocks for fun and surprises at the Hiller Haunted Hangar Halloween party.

October 27, Fall Harvest Festival at Farmers Market Bay Meadows. The Harvest Festival returns to Bay Meadows on the last day of the season! FMBM is planning a Sunday filled with all your fall favorites, plus some helpful workshops and how-to’s just in time for the holidays. Think pumpkins, corn, apples, spices, music and much more! Tin Pot Creamery will sample their latest seasonal flavor from 11am to 2pm and ROAM Artisan Burgers will sample their NEW Autumn Salad! Click here to invite San Mateo neighbors and view the line-up:

October 27, Kids’ Carnival and Helicopter Pumpkin Drop. Paint the Cessna Cardinal airplane, sit in an airplane or helicopter, build a flying craft project and more in a morning of high-flying fun.

October 30, Haunted Howl-o-ween Party for Dogs. Grab your pups and head over to Wag Hotel in Redwood City and find a haunted hotel waiting for you and your pooch to explore!


Conveniently located between San Francisco and Palo Alto in San Mateo, Bay Meadows offers new homes for sale and for rent within walking distance of Caltrain. Ease of transportation is only one reason you’ll fall in love with Bay Meadows. Smartly-designed, high-quality new homes sit among 18 acres of open space, which includes parks, a community garden, public art, ball fields, bocce and basketball courts and a new playground. All this just a walk from Whole Foods, Blue Bottle Coffee, Fieldwork Brewing Co., LIFT Fitness, Tin Pot Creamery, Hillsdale Shopping Center and more. Learn more about what Midurban life offers by following our Facebook page.