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.
2025 Dates TBD
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.
2025 Dates TBD
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.
2025 Dates TBD
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.
2025 Dates TBD
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.
2025 Dates TBD
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!
