Whether you’re a foodie, runner, music lover, or just want to enjoy the early fall vibes, there’s something fun for everyone.

Let’s dive in!

1. Chicano Soul Fest Carshow & Concert – San Jose

Saturday, September 6
📍 History Park, San Jose
A vibrant celebration of lowrider culture, music, and art — with over 200 custom cars on display. This is more than a car show — it’s a soulful party with live performances, food vendors, and a strong sense of community pride.
🔗 historysanjose.org

2. The Gatsby Picnic — San Jose

Sunday, September 14
📍 History Park San Jose
Channel your inner 1920s with a flapper-style picnic, swing music under the oaks, vintage fashion, and flowing champagne. A unique throwback experience!

🔗 Ticketed Event | Book Now

3. Los Gatos Art & Wine Festival – Fiesta de Artes

September 20–21
📍 Civic Center Lawn, Los Gatos
One of the most beloved community events in the South Bay, featuring 200+ artists, live music, local wines, and delicious eats. Family‑friendly with a creative vibe all weekend long.
🔗 losgatoschamber.com

4. Island Running Festival – Alameda

Sunday, September 21
📍 Alameda Point & Faction Brewery
Lace up for this scenic run on the island! Choose from 5K, 10K, or half marathon routes, followed by a beer garden celebration at Faction Brewing. Great for all levels — or just come cheer on your runner!
🔗 runsignup.com

5. Downtown Campbell Farmers' Market – Campbell

Sunday, September 7 (and every Sunday)
📍 Downtown Campbell
A cozy weekly tradition with fresh produce, handmade goods, flowers, and bites from local artisans. Perfect for a relaxed morning with coffee in hand and live music in the background.

🔗 downtowncampbell.com

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See you out there! 👋

— Anna Fine Group

📍 Serving San Jose, Los Gatos, Campbell, Sunnyvale & the entire South Bay