Santa Clara County is packed with things to do this weekend, from art and wine festivals to professional sports, live music, family activities and a home-and-outdoor-living showcase. Whether you want to explore downtown Los Gatos, cheer inside Levi’s Stadium or enjoy a relaxed afternoon close to Almaden Valley, there is something for nearly every interest.
Here are eight fun events happening around Santa Clara County on Saturday, September 19, and Sunday, September 20, 2026.
1. Santa Clara Art & Wine Festival
When: Saturday, September 19, 10:00 a.m.–6:00 p.m.; Sunday, September 20, 10:00 a.m.–5:00 p.m.
Where: Central Park, 909 Kiely Boulevard, Santa Clara
Best for: Art lovers, families and a relaxed community outing
The 44th Annual Santa Clara Art & Wine Festival is one of the weekend’s best all-around community events. Central Park will come alive with distinctive artwork, food, premium wine and beer, live entertainment and activities for different ages.
It is a great choice when everyone in your group wants something a little different. Adults can browse art and sample local flavors while families enjoy the festive outdoor atmosphere. Give yourself time to walk the booths, listen to the entertainment and enjoy the park.
Learn more: City of Santa Clara
2. Taste of Los Gatos
When: Saturday, September 19, noon–5:00 p.m.
Where: Downtown Los Gatos
Best for: Foodies, couples and groups of friends
Historic downtown Los Gatos becomes a pedestrian-friendly celebration of local food, wine, shopping and music during Taste of Los Gatos. Guests can stroll through downtown, sample participating restaurants and discover the personality of one of Santa Clara County’s most charming communities.
This is an especially appealing choice for a date afternoon or a gathering with friends. Tasting wristbands are required for the official food-and-wine experience, and check-in begins at 11:30 a.m. Because it is a popular event, purchasing tickets and planning transportation ahead of time is wise.
Learn more: Town of Los Gatos event calendar
3. Village Fest 2026
When: Saturday, September 19, 11:00 a.m.–4:00 p.m.
Where: Village Oaks Shopping Center, 5700 Village Oaks Drive, San Jose
Best for: Families and South San Jose residents
Village Fest is a free, community-centered street festival designed to bring South San Jose neighbors together. The celebration includes live music, family activities, art, food, local businesses and community organizations.
For residents of Almaden Valley and South San Jose, this is one of the weekend’s most convenient family-friendly options. It offers an easy way to support nearby businesses, connect with neighbors and enjoy a lively afternoon without traveling far from home.
Learn more: San José District 2 Village Fest
4. Bay Area Tri-County Home & Outdoor Living Expo
When: Saturday and Sunday, September 19–20
Where: Santa Clara County Fairgrounds, 344 Tully Road, San Jose
Best for: Homeowners, buyers, sellers and renovation enthusiasts
The Bay Area Tri-County Home & Outdoor Living Expo combines four experiences into one weekend: a home-remodeling and outdoor-living expo, a boat and adventure showcase, a food-truck festival and an interactive game-show experience.
Visitors can meet remodeling and landscaping professionals, explore outdoor kitchens and smart-home ideas, watch demonstrations and look for inspiration for their next project. For homeowners preparing to update a property—and sellers considering improvements before going on the market—it may be one of the most useful events of the weekend.
Admission is free, although advance ticket registration is encouraged.
Learn more and register: Bay Area Tri-County Expo
5. Crafternoons at the Almaden Quicksilver Mining Museum
When: Saturday and Sunday, September 19–20, noon–4:00 p.m.
Where: Casa Grande, Almaden Quicksilver County Park
Best for: Children, families and local-history fans
Families looking for a creative and educational activity close to home can visit the Almaden Quicksilver Mining Museum for Crafternoons. Participants can learn about local wildlife, nature and history while making a craft to take home.
The setting is part of the fun. Casa Grande provides a fascinating glimpse into Almaden’s mining heritage, while the surrounding county park makes it easy to pair the museum visit with a walk or time outdoors. This is a relaxed, budget-friendly addition to a family weekend.
Learn more: Santa Clara County Parks calendar
6. San Jose Earthquakes vs. LAFC
When: Saturday, September 19; kickoff at 4:30 p.m.
Where: Levi’s Stadium, Santa Clara
Best for: Soccer fans and an energetic group outing
The San Jose Earthquakes face Southern California rival LAFC in a marquee Major League Soccer match at Levi’s Stadium. The stadium’s Fan Fest opens at 1:30 p.m., followed by stadium gates at 2:30 p.m., allowing supporters to make an entire afternoon of the game.
This matchup should deliver plenty of energy, whether you are a devoted Earthquakes supporter or simply enjoy the excitement of live professional sports. Allow extra travel time because the game will bring heavier traffic to the Levi’s Stadium area.
Learn more: Levi’s Stadium event information
7. Total Vibez Live San Jose
When: Saturday, September 19
Where: Discovery Meadow, 180 Woz Way, San Jose
Best for: R&B and hip-hop fans and a lively adults’ outing
Ready for a little 2000s nostalgia? Total Vibez Live brings the soundtrack of the era to Discovery Meadow with a day devoted to R&B and hip-hop favorites. The outdoor setting and festival atmosphere make this one of the weekend’s liveliest entertainment options.
It is a natural choice for friends who want to trade a quiet Saturday night for music, dancing and a memorable downtown San Jose experience. Check the festival’s current ticket and entry information before heading out.
Learn more: Visit San Jose
8. Miami Dolphins vs. San Francisco 49ers
When: Sunday, September 20; kickoff at 1:25 p.m.
Where: Levi’s Stadium, Santa Clara
Best for: Football fans and a classic fall Sunday
The San Francisco 49ers return to Levi’s Stadium for an early-season matchup against the Miami Dolphins. Few activities say fall quite like an afternoon of NFL football, and fans can expect a high-energy crowd in Santa Clara.
If you are attending, plan for stadium traffic, parking restrictions and increased activity throughout the surrounding area. Arriving early will leave more time to enjoy the pregame atmosphere and get through security before kickoff.
Learn more: San Francisco 49ers
How to Choose Your Weekend Adventure
With so many choices, here is a quick way to narrow the list:
- Best overall community event: Santa Clara Art & Wine Festival
- Best food-and-wine outing: Taste of Los Gatos
- Best free family festival: Village Fest
- Best for home inspiration: Bay Area Tri-County Home & Outdoor Living Expo
- Best Almaden Valley family activity: Crafternoons at Almaden Quicksilver
- Best for soccer fans: Earthquakes vs. LAFC
- Best live-music experience: Total Vibez Live
- Best major sporting event: Dolphins vs. 49ers
A Weekend That Showcases the Santa Clara County Lifestyle
Weekends like this demonstrate why Santa Clara County continues to be such an attractive place to live. Residents have access to neighborhood festivals, professional sports, outdoor recreation, excellent dining, arts and cultural experiences—all within a relatively short drive.
From the natural beauty and local history of Almaden Valley to the restaurants of downtown Los Gatos and the major entertainment venues of Santa Clara and San Jose, the county offers an unusual variety of experiences. These amenities do more than fill a weekend calendar. They help create connected communities and contribute to the lifestyle homebuyers value when deciding where to live.
Which event will make your weekend list?
Event schedules, admission policies and ticket availability can change. Confirm current details with the event organizer before leaving home.