Fall weekends have arrived, and the Bay knows how to do it right
Pumpkins after dark, art walks, Oktoberfest, live jazz + more worth leaving the house for.
Historical edition. Event dates, offers, and availability reflect the original publication.
Bay of Life Social
YOUR ALGORITHM FOR A BETTER NIGHT OUT.
SEP 28, 2026 · ISSUE NO. 5
“Good evening, Bay.”
We are kicking off spooky season off right with the perfect autumn vibes.
I’m so excited to explore new places, events, and pop ups with you all during one of my favorite seasons.
Check out edition #5, get off your devices and live a little.
This Weekend
Pumpkins After Dark — Pleasanton
Oct 2 · 7:15–10 PM · Alameda County Fairgrounds, Pleasanton · Adults $28, Youth $22, Parking $15
Pumpkins After Dark transforms an evening out into a memorable Halloween spooky experience. Explore illuminated pumpkin displays, enjoy live entertainment, demonstrations, photo stops, and even indulge in seasonal treats.
This Weekend
Mid-Autumn Festival at Filoli
Oct 3 · 10 AM–5 PM · Filoli, Woodside · $39+
Autumn transforms Filoli into a celebration of the season. Stroll through the Garden to discover pumpkins, giant gourds, scarecrows, ornamental grasses, and a vintage red pick up truck.
This Weekend
Palo Alto Art Walk + Art & Dine
Oct 3 · 5–7 PM · Participating downtown Palo Alto galleries and restaurants, Palo Alto · Free
Visit participating galleries for postcard stamps; participating restaurants offer 20% off an appetizer or coffee drink. Includes several downtown galleries; verify exact participation.
Eat + Drink
Oktoberfest at San Pedro Square Market
Oct 3 · Noon–5 PM · San Pedro Square Market, San Jose · $20
October 3, 2026 noon–5 pm beer, food, live music and contests; ticket includes a stein and one half-liter pour. T
This Weekend
Drunken Film Fest Oakland: Opening Night
Oct 3 · Shapeshifters Cinema, Oakland
Check out this one of a kind, free pop-up film festival that brings independent films to bars (and theaters) throughout the Bay!
This Weekend
PortFest 2026
Oct 3 · 10:30 AM–3:30 PM · Port of Redwood City, Redwood City · Free
Waterfront festival with marine science boat trips, kayaking, sailing, music and kids water play. Reserve limited tours separately.
This Weekend
52nd Castro Street Fair: Where We Belong
Oct 4 · 11 AM–6 PM · Castro neighborhood, San Francisco
Street celebration with local artisans, vendors, entertainment, live music and dancing.
This Weekend
Jazz Festival in the Vineyards
Oct 4 · 11 AM–6 PM · Wente Family Vineyards, Livermore · General admission $65
Rick Braun, Eric Darius, Blake Aaron, Marcus Anderson and Erin Stevenson headline a vineyard jazz day. Bring your blankets, lawn chairs, and friends. Kick back and enjoy some live music with beer, wine, cocktails, and more.
Bay of Life Social
“Your algorithm for a better night out.”
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