Best Things to Do in the South Bay This September

Best Things to Do in the South Bay This September

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.

No need to bundle up in the South Bay during this month, temperature averages are in the 70s.

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

A bustling street fair with a diverse crowd under a banner that reads, "Millbrae Art & Wine Festival," one of the best things to do in South Bay this September. Booths line both sides of the street, selling food and crafts. People enjoy the sunny day, wearing hats and casual clothing amid palm trees and buildings.
Photo courtesy of Millbrae Art & Wine Festival.

Dates TBD

Stroll, browse, relax and enjoy the vibrant end-of-summer celebration. This two-day festival features live music, hand-crafted wares by nearly 300 talented artists and crafters, delicious food and more. On Saturday, the Classically Cool Car Show takes center stage at the festival.

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.

Dates TBD

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 1–9 p.m., with el Grito happening at 7:30 p.m. 

A live band performs on a covered outdoor stage with a sign reading "Summers End Music" behind them. Several people in casual clothing dance and enjoy the music in front of the stage. The scene, one of the best things to do in South Bay September, takes place on a sunny day, with trees and street lamps visible.
Photo courtesy of Summer's End.

Dates TBD

Not much of an excuse is needed to venture down Highway 1, but here’s a good one: Half Moon Bay’s annual Summer’s End Music Festival, held in its historic downtown corridor. Along with plenty of good music, the festival offers climbing walls, caricature drawings, face painting, henna tattoos, cornhole, an inflatable obstacle course and a kid’s activity area.

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.

Dates TBD

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.

Dates TBD

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!

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top