Looking for things to do in San Jose this weekend? From Oktoberfest in Campbell and a Diwali festival in Cupertino to RUSH at SAP Center, closing weekend of The Phantom of the Opera and a giant-pumpkin parade on the coast, these Silicon Valley events for Friday, October 16 through Sunday, October 18, 2026 have something for every age, budget and mood.
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This weekend is packed with fun, excitement, and things to do around San Jose! Whether you’re looking for music, art, food, or unique experiences, there’s something for everyone to enjoy.
Below you’ll find South Bay weekend events organized by day, with the venue, time, cost and a link to each event, so you can plan your October 2026 events in a few minutes. Times and prices can change, so confirm with the organizer before you go.
Honorable Mention: Half Moon Bay Art & Pumpkin Festival (Oct. 17–18)
It’s a drive over the hill from the South Bay Area, but this coastside classic is worth the trip if you love pumpkin patches and fall traditions.
54th Half Moon Bay Art & Pumpkin Festival on Main Street
The “World Pumpkin Capital” celebrates its biggest weekend with 250 top artists, four stages of live music, pumpkin treats, and pie-eating contests along historic Main Street. Don’t miss the Great Pumpkin Parade Saturday at noon, starring this year’s 2,389-pound champion pumpkin, “Rocky.” Admission is free!
Where: Main Street, Half Moon Bay
When: Saturday, Oct. 17th – Sunday, Oct. 18th
Cost: Free
Event page: Half Moon Bay Art & Pumpkin Festival event details
Friday, Oct. 16: Things to Do in San Jose Tonight
Kick off the weekend in San Jose with a Broadway classic or a family Halloween party.
The Phantom of the Opera at the San Jose Center for the Performing Arts (Friday)
Andrew Lloyd Webber’s legendary musical, seen by 160 million people worldwide, plays its final San Jose weekend with a 7:30 PM show.
Where: San Jose Center for the Performing Arts
When: Friday, Oct. 16, 7:30 PM
Cost: $40 Rush
Event page: The Phantom of the Opera tickets at Broadway San Jose
Berryessa Boo Bash: Family Halloween Party in San Jose
A family Halloween party from 6–8:30 PM with crafts, costumes, prizes, and a haunted-house walkthrough (advance registration required).
Where: Berryessa Community Center
When: Friday, Oct. 16, 6–8:30 PM
Cost: $12 per child
Event page: Berryessa Boo Bash registration (City of San Jose)
Saturday, Oct. 17: Silicon Valley Events, Festivals and Games
Saturday is the biggest day of the weekend for Santa Clara County events, with free festivals in Campbell, Sunnyvale and Cupertino, plus concerts and games across the Silicon Valley.
31st Annual Campbell Oktoberfest (Saturday)
Downtown Campbell becomes a German street festival from 10 AM–6 PM with beer, brats, oompah music, 100+ craft booths, and a 2 PM stein-holding contest.
Where: Downtown Campbell
When: Saturday, Oct. 17, 10 AM–6 PM
Cost: Free
Event page: Campbell Oktoberfest event page
Day Trip Festival NorCal at Discovery Meadow (Saturday)
Insomniac’s beloved house and techno festival makes its first-ever NorCal stop, with Gordo b2b Vintage Culture headlining from 2–10 PM (18+).
Where: Discovery Meadow
When: Saturday, Oct. 17, 2–10 PM (18+)
Cost: $79.99+
Event page: Day Trip Festival NorCal tickets
41st Annual Hands on the Arts Festival in Sunnyvale
A free kids’ festival from 10 AM–3 PM celebrating art from around the world with hands-on workshops and performances all day.
Where: Sunnyvale Community Center
When: Saturday, Oct. 17, 10 AM–3 PM
Cost: Free
Event page: Hands on the Arts Festival details (City of Sunnyvale)
Cupertino Diwali Festival at Memorial Park
One of the South Bay’s biggest cultural celebrations returns from 11 AM–6 PM with music, dance, Indian food, and a kids’ zone.
Where: Memorial Park, Cupertino
When: Saturday, Oct. 17, 11 AM–6 PM
Event page: Cupertino Diwali Festival listing on South Bay Today
The Phantom of the Opera in San Jose (Saturday Matinee and Evening)
Catch the 2 PM matinee or 7:30 PM show of the iconic musical, perfect for a family outing or date night.
Where: San Jose Center for the Performing Arts
When: Saturday, Oct. 17, 2 PM and 7:30 PM
Cost: $40 Rush
Event page: Saturday Phantom of the Opera tickets
RUSH: Fifty Something Tour at SAP Center
The Rock Hall legends tour for the first time in 11 years, playing two full sets of classics like “Tom Sawyer” at 7:30 PM.
Where: SAP Center
When: Saturday, Oct. 17, 7:30 PM
Event page: RUSH at SAP Center event page
San Jose Earthquakes vs. Nashville SC at PayPal Park
The playoff-hunting Quakes host East-leading Nashville at 7:30 PM on First Responders Night, hosted by Guy Fieri.
Where: PayPal Park
When: Saturday, Oct. 17, 7:30 PM
Event page: Earthquakes vs. Nashville SC match page
Stanford Football vs. Elon: Homecoming at Stanford Stadium
Cheer on the Cardinal at the 4:30 PM Homecoming game, a first-ever matchup and Elon’s first West Coast game.
Where: Stanford Stadium
When: Saturday, Oct. 17, 4:30 PM
Event page: Stanford vs. Elon Homecoming game details
Potrero Hill Rhythm & Blues Festival in San Francisco
This 51-year-old neighborhood party fills four blocks with R&B on two stages, local food, a beer garden, and a kids’ fun fair starting at 10 AM.
Where: 20th St, San Francisco
When: Saturday, Oct. 17, starting at 10 AM
Cost: Free
Event page: Potrero Hill Rhythm & Blues Festival listing
Sunday, Oct. 18: South Bay Weekend Events to Close It Out
Sunday brings day two of Oktoberfest and Day Trip, a supercar meetup at Santana Row, pro soccer and your last chance to catch Phantom in San Jose.
31st Annual Campbell Oktoberfest, Day Two (Sunday)
Day two runs 10 AM–5 PM with more beer, brats, and street-fair fun, plus a Kids Zone for the little ones.
Where: Downtown Campbell
When: Sunday, Oct. 18, 10 AM–5 PM
Cost: Free
Event page: Campbell Oktoberfest Sunday details
Day Trip Festival NorCal, Day Two (Sunday)
Day two (2–10 PM, 18+) brings Cloonee and a special After Midnight set to an open-air dance floor under the downtown skyline.
Where: Discovery Meadow
When: Sunday, Oct. 18, 2–10 PM (18+)
Cost: $79.99+
Event page: Day Trip Festival Sunday tickets
Cars & Croissants on The Row at Santana Row
Grab a coffee and stroll past supercars and rare exotics at one of the world’s premier exotic car meetups from 9 AM–12 PM.
Where: Santana Row
When: Sunday, Oct. 18, 9 AM–12 PM
Cost: Free
Event page: Cars & Croissants on The Row event page
Hocus Pocus Drag Brunch at the San Jose Improv
A spooky, immersive 21+ drag brunch at 1 PM with performers from around the country, perfect for a group of friends.
Where: San Jose Improv
When: Sunday, Oct. 18, 1 PM (21+)
Cost: $31+
Event page: Hocus Pocus Drag Brunch tickets
Bay FC vs. Portland Thorns FC at PayPal Park
Bay FC hosts NWSL powerhouse Portland at 2 PM, with FanFest opening at noon with food trucks, games, and giveaways.
Where: PayPal Park
When: Sunday, Oct. 18, 2 PM (FanFest opens at noon)
Cost: $12+
Event page: Bay FC vs. Portland Thorns match page
The Phantom of the Opera: Closing Day in San Jose
It’s closing day, with your last chances at 1 PM and 6:30 PM before the Phantom leaves San Jose.
Where: San Jose Center for the Performing Arts
When: Sunday, Oct. 18, 1 PM and 6:30 PM
Cost: $40 Rush
Event page: Phantom of the Opera closing-day tickets
John Mulaney: Mister Whatever at The Mountain Winery, Saratoga
The four-time Emmy winner brings his new stand-up tour to the hillside Mountain Winery at 7:30 PM.
When: Sunday, Oct. 18, 7:30 PM
Event page: John Mulaney: Mister Whatever tickets on AXS
Planning More Things to Do in San Jose and the South Bay This Fall
If you’re mapping out the rest of October 2026, next Saturday brings the free San Jose Diwali Carnival downtown, and there are plenty more fall activities in the South Bay Area, from pumpkin patches to Halloween events. For more ideas across Santa Clara County, the Visit San Jose events calendar is a helpful resource.
Thinking about living in downtown San Jose, or relocating to Silicon Valley and want to explore South Bay neighborhoods on a weekend like this one? I’m always happy to help you get to know the area. Just reach out.
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