Best Things to Do in the South Bay This October

Best Things to Do in the South Bay This October

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. 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.

Oct. 4–6

At this highly unusual 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.

Oct. 12–13

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.

Oct. 19–20

Half Moon Bay is known, at least in Northern California, as the “pumpkin capital of the world.” The town throws a heck of festival to celebrate all things orange and gourd-like, including record-breaking pumpkins that can weigh thousands of pounds (the current world champion from 2023 weighs 2,749 lbs.), 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.

Oct. 20

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.   

A person, wearing a white shirt and a gold ring, is pouring a yellow beverage from a bottle into a glass. Multiple empty glasses line up on the table in front of them. Among the Best Things to do South Bay October, savoring this moment stands out vividly.
Photo by Fabio Alves via Unsplash.

Oct. 26

Join the locals at the annual Los Gatos Beer & Wine Walk. You can sip on tastings from dozens of wineries and breweries in the Bay Area, plus enjoy the many restaurants and shopping options in chic, downtown Los Gatos. Purchase your tickets while they last!

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