Fall 2026 Events Around Silicon Valley & the Peninsula

Fall is here, and there’s plenty happening around Silicon Valley and the Peninsula!

From art and wine festivals to cultural celebrations, live entertainment, family activities, and one of the Bay Area’s most iconic pumpkin festivals, the next few weeks are packed with opportunities to get out and enjoy the communities we call home.

Whether you’re looking for something to do with the family, planning a weekend with friends, or simply want to explore another part of the Bay Area, here are a few events worth adding to your calendar this fall.

Event details can change, so be sure to check with the event organizer before heading out.

Los Gatos Art & Wine Festival:

• September 26–27 | 10:00 AM–6:30 PM
• Civic Center Lawn | 110 E. Main St., Los Gatos
• Admission: Free

Spend a fall weekend in Los Gatos enjoying art, music, food, wine, and plenty of community spirit. This long-running festival has been a local tradition for more than 50 years and is organized by the Kiwanis Club of Los Gatos.

Beyond being a fun weekend out, the event also serves as the organization’s largest annual fundraiser, with proceeds supporting scholarships, youth programs, and other community initiatives.

It’s a great excuse to spend the day in Los Gatos, browse, listen to music, grab something to eat, and enjoy one of Silicon Valley’s favorite local traditions.

https://losgatosfiesta.com

 Pacific Coast Fog Fest — Pacifica:

• September 26–27 | 10:00 AM–6:00 PM
• Palmetto Avenue | Pacifica
• Admission: Free

Ready for a trip to the coast? Pacifica’s Pacific Coast Fog Fest returns for its 39th year with a full weekend of entertainment and activities along Palmetto Avenue.

Visitors can explore more than 200 arts, crafts, and vendor booths, catch live music, grab festival food and drinks, and enjoy activities for the whole family. Saturday morning also kicks off with the festival parade, while other weekend attractions include the Family Fun Fest and Fog Jog. 

It’s an easy way to turn a fall weekend into a coastal day trip without going too far from Silicon Valley.

https://pacificcoastfogfest.com

Kasayahan Sa Daly City:

• October 3 | 11:00 AM–4:00 PM
• Gellert Park Complex | 50 Wembley Drive, Daly City
• Admission: Free

Celebrate Filipino American History Month with an afternoon dedicated to Filipino culture and community in Daly City.

Kasayahan Sa Daly City brings together food, cultural performances, music and dance, local vendors, live entertainment, and activities for families at the Gellert Park Complex. 

With something for different ages and interests, it’s a fun opportunity to experience and celebrate the traditions that are such an important part of the Bay Area’s diverse communities.

https://www.instagram.com/dalycityrec/

Diwali 2026 — Sunnyvale:

• October 3 | 11:30 AM–7:30 PM
• 230 S. Murphy Ave. | Downtown Sunnyvale
• Admission: Free

Downtown Sunnyvale will come alive with music, dance, food, color, and culture for the South Asian Cultural Association of Sunnyvale’s 2026 Diwali celebration.

The day’s lineup includes Indian classical dance performances and Bollywood flash mobs, along with vendors offering Indian handicrafts, clothing, and jewelry. Visitors can also enjoy Indian food, henna, photo booths, and plenty of family-friendly activities.

For younger visitors, the Kids’ Zone includes face painting, a diya painting competition, bookmark workshops, and balloon activities. 

It’s a wonderful opportunity to experience one of the area’s vibrant cultural celebrations right in the heart of Sunnyvale.

https://www.sacas.org

San Carlos Art & Wine Faire:

• October 10–11 | 10:00 AM–6:00 PM
• San Carlos Avenue & Laurel Street | Downtown San Carlos
• Admission: Free

Downtown San Carlos transforms into a lively outdoor festival for its annual Art & Wine Faire.

More than 200 artists, crafters, and specialty vendors are expected to fill the streets with everything from paintings and photography to ceramics, jewelry, woodworking, clothing, and other handcrafted finds.

Add wine, microbrews, festival food, live entertainment, and a Family Fun Zone with hands-on activities for kids, and there’s plenty to fill an afternoon—or an entire day. 

It’s a particularly nice option if you want to combine a local festival with some time exploring downtown San Carlos.

https://www.cityofsancarlos.org/city_hall/departments_and_divisions/parks_and_recreation/community_events.php

Half Moon Bay Art & Pumpkin Festival:

• October 17–18 | 9:00 AM–5:00 PM
• Main Street | Half Moon Bay
• Admission: Free

It wouldn’t feel quite like fall in the Bay Area without a trip to Half Moon Bay.

The 54th annual Half Moon Bay Art & Pumpkin Festival returns to historic Main Street for a weekend celebrating all things autumn—and, of course, pumpkins.

Festival-goers can browse work from hundreds of artists and craftmakers, enjoy multiple stages of live entertainment, catch the Great Pumpkin Parade, sample seasonal food and drinks, and take part in a variety of festival activities. 

And the celebration actually starts before festival weekend. Moonlight Movie Night is scheduled for October 10, followed by the famous World Championship Pumpkin Weigh-Off on October 12.

If you’re looking for the quintessential Bay Area fall outing, this one is hard to beat.

https://hmbpumpkinfest.com

Enjoy Fall Around Silicon Valley:

One of the best things about living in Silicon Valley and the greater Bay Area is just how much there is to experience beyond our own neighborhoods.

Within a relatively short drive, you can spend a morning at a community festival in Los Gatos, experience Diwali in Sunnyvale, explore art in downtown San Carlos, celebrate Filipino culture in Daly City, head to Pacifica for a coastal festival, or make a fall day trip to Half Moon Bay.

We’ll continue sharing local events, seasonal activities, and things to do around the area, so check back for more ideas throughout the year.

Know about a great local event we should feature next? We’d love to hear about it!

Dates, times, activities, admission policies, and other event details are subject to change. Always confirm the latest information directly with the event organizer before attending.