Best Things to Do in the South Bay This September

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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.

Looking for the coolest things to do at the beginning of the fall season? From Labor Day to the equinox, we’ve got you covered. We’ve done the deep research for you on the best things to do in the South Bay this September including museums, cultural events, food tours and more. Speaking of food, we also have an extensive list of our best restaurants in the South Bay – and if you’re planning a weekend, the best places to stay.

Best of all? There’s no need to bundle up in the South Bay during this month, since average temperatures are in the 70s!

Featured photo courtesy of Comité de Fiestas Patrias de San José, California Facebook.

Crowd walking through the Mountain View Art and Wine Festival
Photo courtesy of Mountain View Art and Wine Festival.

September 6-7

Mountain View
Castro St

The festival features 350 of America’s finest artists and craftmakers, live music, the Pigskin Party Lounge with football and baseball on the giant screen TV, and curated food and drink purveyors with premium wine, sangria, seasonal craft beer, hard cider, seltzer and signature cocktails. There’s also a Kids Funzone with cornhole tossing and other activities. 

A group of dancers in colorful traditional dresses perform on an outdoor stage, their skirts swirling as they dance. Behind them, a large Mexican flag is prominently displayed. In the foreground, people are seated and watching the performance—one of the best things to do in South Bay this September. A podium with the City of San Jose emblem is also visible.
Photo courtesy of Comité de Fiestas Patrias de San Jose Facebook.

September 15

San José
200 E. Santa Clara St

Every September 15, the day before Mexico’s Independence Day, Mexicans worldwide gather to reenact “el Grito,” the cry uttered by Miguel Hidalgo y Costilla which declared freedom from Spanish colonization. San José does the same in front of its city hall, and thousands of community members participate in the show of Mexican pride. A day-long celebration includes folklore dancers, mariachi and delicious food from 4–9 p.m., with el Grito happening at 7:30 p.m. 

Children run a race as part of the Half Moon Bay Beach Safety Run
Photo courtesy of Arunay Foundation.

September 21

Half Moon Bay
1 Johnson Pier

This destination event will host 5K and 10K courses that will showcase the beautiful Pillar Point Harbor and its docks of colorful fishing boats and ever-present ocean views from the Pillar Point Marsh Trail. A noncompetitive Kids Fun Run (1/4 Mile) for ages 10 and under will conclude the morning. The event is a benefit for the Arunay Foundation, which is committed to reducing beach accidents and coastal drownings by educating about sneaker waves, rip currents and other hazardous conditions. 

A group of people, including adults and children, riding bikes on a suburban street lined with parked cars and trees on a sunny day. The riders wear helmets and appear to be enjoying their ride, with some smiling and others chatting—one of the best things to do South Bay September.
Photo courtesy of City of Cupertino Facebook.

September 27

Cupertino
10201 Torre Ave

Bike rodeo, family rides and even a pedal-powered blender for smoothies — this fall bike fest covers all things two-wheeled. Bring the kids along for helmet checks and safety lessons before embarking on a 2.5-mile ride through Wilson Park. Games, crafts and Cupertino’s library truck will also be part of the event. 

A group of people in a parade holds various banners, including a prominent "Grand Marshal" sign. They are walking near a red double-decker bus filled with people on an overcast day. Some participants are in uniform, while a person in a yellow vest directs the procession – one of the best things to do South Bay September.
Photo courtesy of Fog Fest.

September 27-28

Pacifica
Palmetto Ave

Fog Fest was created in 1986 to celebrate Pacifica and its marvelous coast – plus it’s almost always great weather during the last weekend in September when it’s traditionally held. Kicking off with a parade down Palmetto Avenue, the festival continues with musical performances, food and beverages, contests and plenty of amusement games and rides for the kids. 

Event Venues

Looking to see what’s happening right now in the South Bay? Our comprehensive list of venues below will help you find what you need to know what’s going on.

Looking for more things to do in the area?

Visit our What to Do in Northern California page!

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