Best Things to Do in the South Bay This October

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David Sason

David is a Marin County native and longtime columnist who's written arts & entertainment pieces for the North Bay Bohemian, KQED, Metro Silicon Valley, the Bay Area Reporter and more.

Not sure what to do this month? With so many offerings in the South Bay region, we’ve curated some of the top events this month so you don’t have to. Here are the best things to do in the South Bay this October. That means less researching and more enjoying your time in the area. Enjoy!

Featured photo: Half Moon Bay Pumpkin Festival, photo by Igor Porton. 

A wooden crate filled with a variety of colorful glass pumpkins lies on a bed of straw. The pumpkins come in assorted colors, including gold, white with orange patterns, red, and green. Each has a distinct textured glass stem. Discover one of the best things to do in South Bay this October!
Photo courtesy of Santana Row.

October 3-5

San Jose

377 Santana Row

At this unique pumpkin patch at Santana Row Park, stroll through thousands of hand-blown glass pumpkins crafted by artists from the Bay Area Glass Institute, as well as renowned glass artisans from around the country. You can even pick up one to take home. 

Three women are smiling and holding drinks at an outdoor event, one of the best things to do in South Bay this October. They are all wearing sunglasses and casual clothing, with a crowd of people and various event booths visible in the background. The atmosphere appears lively and sunny.
Photo courtesy of San Carlos Art Faire Facebook.

October 11-12

San Carlos

San Carlos Avenue at Laurel Street

Browse hundreds of artisan booths as you sip wine from local and global wine makers, mingle with other shoppers and listen to live music at this popular event in downtown San Carlos. 

Four smiling kids stand in a row under a clear sky, each holding a pumpkin. They appear happy and excited, dressed in casual clothes, enjoying a bright, sunny day—truly one of the best things to do in South Bay this October.
Photo courtesy of Igor Porton for the Half Moon Bay Pumpkin Festival/Miramar Events.

October 18-19

Half Moon Bay

Main Street

Half Moon Bay is known, at least in Northern California, as the “pumpkin capital of the world.” The town throws a heck of a festival to celebrate all things orange and gourd-like, including record-breaking pumpkins that can weigh thousands of pounds, plus pumpkin carving, pumpkin pie eating contests, costume contests and much more. 

Three smiling women, dressed in traditional attire and adorned with medals, pose together outdoors. The woman on the left sports a floral crown, the one in the middle wears a headband, and the woman on the right has her hair tied back. It's one of the best things to do in the Bay Area October festivities.
Photo courtesy of Campbell Chamber Oktoberfest.

October 18-19

Campbell

East Campbell Avenue, between Third Street and Harrison Avenue

Since 1994, the charming community of Campbell has attracted almost one million people to its annual Oktoberfest for two days of Bavarian-themed festivities. While there are the usual varieties of German food and beer offerings, this festival also has steinholding and best-dressed contests, along with dozens of bands playing everything from traditional German music to soul, pop and rock and roll.   

Girls and their dogs enjoy the Halloween Kid and Pet PAWlooza in Los Gatos.
Photo courtesy of Arnold Briet.

October 26

Los Gatos

Los Gatos Town Plaza Park, Montebello Way

Trick or treat with the vendors downtown and participate in a “Pawrade of sorts,” a party for both children and animals in downtown Los Gatos. This event is a Fundraiser for the Street Dog Coalition. Bring your pet, your family and your friends dressed in costumes. Trick or treating with the children starts at the Los Gatos Town Plaza Park.

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