Best Annual Events in the South Bay

You know it best for its shiny nickname “Silicon Valley.” But this part of the bay, about 50 miles south of San Francisco, is not just a global center for more than 2,000 innovative tech companies and home to Adobe, Apple, Cisco, Facebook, Google, HP and Netflix. Palo Alto has tons of greenspace, including 40 miles of walking and biking paths. Walk through Stanford University’s historic campus or opt for the modern Stanford Shopping Center open air mall. Burlingame offers a charming downtown with upscale boutiques, a Shorebird Sanctuary along the Peninsula, and the IT’s-IT Factory, which is still making incredibly delicious ice cream sandwiches.

If you’re traveling with children, or are a youthful spirit yourself, California’s Great America amusement park is in Santa Clara; as is Levi’s Stadium, home of the San Francisco 49ers.

Whatever you do, wherever you go, don’t miss out on the food scene in the South Bay — especially in San Jose. Known for its ethnic diversity in the historic downtown district, find Mediterranean, Hawaiian, Mexican, Californian cuisine (of course) and more.

*Things change, so please check in with the organizers of these events for details.

January

Two women hold hands and smile while ice skating outdoors in front of a decorated Christmas tree, one of the Best Annual Events in the South Bay. They are wearing winter clothing, including hats and sweaters. Other skaters and festive decorations are visible in the background.
Photo: Courtesy of Union Square Ice Rink.

Start the year off with an event that leans into the Silicon Valley’s love for tech in events: Robots on Ice at the Holiday Ice Rink. Or pick up a new hobby with their Learn to Curl workshop, which expands the sport of ice skating beyond its user base.

Read more about the best things to do in the South Bay in January here.

February

A woman dressed in a traditional outfit performs a dance holding a large fan with a white and yellow gradient. Behind her, other dancers with similar fans participate in the performance. The background features colorful painted scenery, embodying one of the Best Annual Events in the South Bay.
Photo: Courtesy of @TetSanJose

Join on one of the biggest Vietnamese New Year Festival in San Jose. The Vietnamese New Year takes place at Eastridge Mall and features live entertainment, lion and dragon dance, contests, carnival rides and games, food booths, and more.

Read more about the best things to do in the South Bay in February here.

March

A can of Brother Paddy Hazy IPA is nestled among vibrant green clover plants. The can features a laughing monkey graphic and shamrocks, giving it a festive, St. Patrick's Day feel that would fit right in at one of the Best Annual Events in the South Bay.
Photo: Courtesy of Laughing Monk Brewing

Head to Los Altos for Saint Paddy’s Day, where downtown hosts a Beer Stroll that combines lives music with craft beer, presumably two of the Irish Saint’s pastimes. Then scoot down to Santa Cruz for their annual Jazz Festival.

Read more about the best things to do in the South Bay in March here.

April

A person wearing a wide-brimmed hat is arranging colorful flowers on a table outdoors. Other people are visible in the background among greenery and vertical garden structures, also engaging in floral activities. The scene is bright and vibrant, reminiscent of the Best Annual Events in the South Bay.
Photo: Courtesy of Filoli

Usher in spring with the help of Filoli’s Horticulture Team: learn the basics of building a floral arrangement, artfully combining a mix of fresh flowers and greenery. Tour the gardens and the house in Woodside; be inspired by the luscious bouquets painted by the Dutch masters.

Read more about the best things to do in the South Bay in April here.

May

A group of children is marching in a street parade. They are holding a large banner that reads "Madison Elementary" and "Addison." The children, dressed casually and in school sports uniforms, appear to be celebrating one of the Best Annual Events in the South Bay.
Photo: Courtesy of Recreation Services, City of Palo Alto

Get out in the sunshine with Palo Alto’s Childrens’ May Festival. It’s grown into one of the major events in Palo Alto, featuring a parade on University Avenue with kids walking their pets, riding their bicycles, pulling their wagons or showing off their homemade floats. 

Read more about the best things to do in the South Bay in May here.

June

A vibrant carnival scene at dusk features a brightly lit Ferris wheel and various amusement rides surrounded by colorful tents and booths. The sky is painted with hues of orange, pink, and purple as the sun sets in the background, showcasing one of the Best Annual Events in the South Bay.
Photo: Courtesy of @SanMateoCoFair

Kick off the summer at the Art & Wine Festival in Downtown Sunnyvale. Follow it up with a visit to the San Mateo County Fair, ogling restored vehicles at an antique car show, or live music at one of the many venues in the area.

Read more about the best things to do in the South Bay in June here.

July

A night sky filled with vibrant fireworks creates a dazzling display of light and color, marking one of the Best Annual Events in the South Bay. Bright bursts of red, purple, and white fireworks are prominently visible against a dark backdrop, while silhouettes of trees and a building with lights are seen below.

One of Northern California’s longest-running fireworks events is at Mountain Views Shoreline Amphitheatre on July 4th, a special celebration with the San Francisco Symphony. On the second weekend of July, downtown Los Altos hosts the two-day Art + Wine Festival showcasing 300 artistshandcrafted works, attracting makers from a dozen states. And the Gilroy Garlic Festival, a major community event known for its garlic ice cream and garlic fries among others, is the last full weekend in July. 

Read more about the best things to do in the South Bay in July here.

August

A large crowd gathers in front of a stage at the San Jose Jazz Festival, one of the best annual events in the South Bay. People are wearing various hats and summer clothing. The stage features a band performing under a banner reading "San Jose Jazz Festival" with sponsor logos. Trees and buildings are in the background.

The San Jose Jazz Summer Fest has been attracting jazz lovers for more than 30 years…plus blues, R&B, Latin, New Orleans, and more. And for those who are pro-dog, hang out on the beach and watch incredible dogs catch some waves at the World Dog Surfing Championships.

Read more about the best things to do in the South Bay in August here.

September

People browsing various jewelry and gemstone displays at an outdoor market, part of the Best Annual Events in the South Bay, under a white tent. The market is set near a fountain in a park with trees in the background. Shoppers and vendors are engaged, examining items on tables covered in red cloths.
Photo: Courtesy of City of Santa Clara Parks & Recreation

The Santa Clara Art & Wine Festival takes place in the 52-acre Central Park and features over 160 art vendors, 25+ food groups, 3 entertainment stages and large children’s area. All proceeds go to local non-profit organizations.

Read more about the best things to do in the South Bay in September here.

October

Two people pose with an enormous, sculpted pumpkin at one of the Best Annual Events in the South Bay. The pumpkin, featuring distinct cracks and a large stem, sits on a bed of hay with clear blue skies and colorful buildings in the background. Both individuals are smiling and appear to be enjoying themselves.

Half Moon Bay is home of the pumpkin. On a peak harvest weekend in mid-October, the Main Street Pumpkin Festival salutes pumpkins, carving skills, art, food, wine, and community. The heaviest of the giant gourds — typically over a ton — is crowned the winner after a weigh-off and then The Great Pumpkin Parade is on. Love Donuts? Who doesn’t. Donut Fest is for those who simply want to enjoy a Sunday Funday while sampling donuts, enjoying beer, coffee and more.

Read more about the best things to do in the South Bay in October here.

November

A fork in a forest trail with dense green foliage and moss-covered trees lining both paths. Sunlight filters through the branches, creating a dappled effect on the dirt trail. A small, brown sign is posted at the fork, indicating trail directions for local getaways.

From concerts to sporting events to theatre and film festival showings, there’s a lot to be thankful for this month in the South Bay. If you’re into getting outdoors, enjoy crunching  autumn leaves as you walk one of the South Bay’s best hikes in the crisp air.

Read more about the best things to do in the South Bay in November here.

December

A nighttime view of a bustling outdoor ice-skating rink encircled by tall palm trees adorned with blue lights. Skaters are enjoying the rink, while nearby buildings and festive decorations create a lively atmosphere. It's one of the Best Annual Events in the South Bay, illuminated by bright lights.
Photo by Greg Ramar.

Celebrate the season with Downtown Ice in San Jose — the only rink in the world that offers skating in and around a circle of 32 palm trees.

Read more about the best things to do in the South Bay in December here.

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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