Bay Area Events | October 2023


It’s fall at last! While we’re still enjoying a glorious Indian Summer, there’s a new morning chill in the air that signals a change of seasons. Apple orchards and pumpkin fields are bursting with color, and it’s a wonderful time of year to explore local farms and enjoy the special fruits of the season.

Here are some of my other favorite fall events where you can drink up the sparkling sun and crisp autumn air in and around our colorful Bay Area:


Spina Farms Pumpkin Patch | Morgan Hill | October 1 – 31

Voted “Favorite Patch in the Bay Area,” this farm lets you enjoy features like the Express Train, hay rides, a corn maze, Pumpkin Blasters, and so much more! It’s no wonder this fall-time community tradition has stayed so popular for over 80 years. For more information and tickets, visit

KRTY Songwriters Series | San Martin | October 5 – 6

Just down the valley in San Martin, relax on a beautiful fall evening under the stars at gorgeous Clos La Chance Winery. Listen to top country songs performed in person by the writers themselves while sipping glasses of delicious wine. For tickets, visit

Fleet Week Air Show | San Francisco | October 6 – 8

Held annually between Golden Gate Bridge and Alcatraz, this waterfront event headlined by the US Navy’s Blue Angels attracts thousands from over the globe. The air show, the parade of ships, ship tours, neighborhood concerts, and many other community events celebrate and honor the contributions of the US Armed Forces. Visit for more info.

Orchard Days at Filoli | Woodside | Saturday & Sundays, October 7 – 29

Enjoy the bounty of fall in Filoli’s Gentleman’s Orchard on Saturdays and Sundays through Oct. 29. Savor the jewel tones of autumn with live music, spiced cider, and good friends. Visit for more info.

51st Annual Art & Pumpkin Festival | Downtown Half Moon Bay | October 14 – 15

This world-renowned festival celebrates all things about the Great Gourd, including a World Champion Pumpkin Weigh-Off on October 9. Enjoy live music, harvest-inspired arts and crafts, pie-eating contests, pumpkin carving, and a parade, plus food, beer, and wine. See more at

Oktoberfest | Downtown Campbell | October 21

Voted Best South Bay Festival, this event covers an entire weekend of live music, arts and entertainment, a costume contest, and of course, great German food and beer! Free admission. Visit campbelloktoberfestcom.

41st Annual Leap Sandcastle Classic | San Francisco | October 28

NorCal’s biggest sandcastle competition is a team event that pairs architects, engineers, contractors, designers, and corporations with local elementary school students who work together to build giant sand sculptures along Ocean Beach. This year’s classic features celebrity judges, live entertainment, and community castles so everyone can join in on the fun and get their hands dirty! Learn more at

Creepy Crawly Halloween | Downtown Campbell | October 29

Don’t miss this two-hour community-wide costume party in the streets! Bring your two- and four-legged little ghouls, goblins, and superheroes to Downtown Campbell’s haunted district for some scary good fun and trick-or-treating. Visit

Halloween Haunt | San Jose | Select Nights Through October 31

San Jose’s eerie Winchester Mystery House presents “Unhinged: Housewarming,” an immersive seasonal experience with a brand-new origin story, new characters, and terrifying scares (not for the faint of heart!). Purchase tickets in advance here.