Here’s your chronological guide to October 2025 events so you can plan your weekends from start to finish.
📅 October 2025 Event Calendar
🌊 PortFest
📅 Saturday, October 4, 2025 | 📍 Port of Redwood City
Kick off October at the waterfront with food trucks, live music, kids’ activities, boat rides, and a community vibe that celebrates Redwood City’s maritime history.
🏆 Safeway World Championship Pumpkin Weigh-Off
📅 Monday, October 13, 2025 (7:00 AM) | 📍 IDES Grounds, Half Moon Bay
Farmers haul in their record-breaking pumpkins — often tipping the scales at over 2,000 pounds. This is the Super Bowl of pumpkins, and the excitement starts at sunrise!
🎨 53rd Annual Half Moon Bay Art & Pumpkin Festival
📅 Saturday & Sunday, October 18–19, 2025 | 📍 Main Street, Half Moon Bay
Pumpkin magic at its peak: parades, pie-eating contests, live music across multiple stages, pumpkin carving, and booths filled with cozy fall flavors and local art.
🏃♀️ Pumpkin Run
📅 Sunday, October 19, 2025 | 📍 Downtown Half Moon Bay
Start the morning with a 5K, 10K, or half marathon — then reward yourself at the Pumpkin Festival with cider, pie, and music.
🍎 Filoli Taste of Fall
📅 Saturday & Sunday, October 18–19, 2025 | 📍 Filoli Historic House & Gardens, Woodside
An elegant fall celebration with artisan vendors, seasonal bites, and cider tastings. The gardens shine with autumn color — a perfect backdrop for photos and family strolls.
🌙 Filoli Nightfall (Evening Series)
📅 October 18 – November 10, 2025 (Evenings) | 📍 Filoli, Woodside
As the sun sets, Filoli transforms into a glowing autumn wonderland. Think lantern-lit trails, fire pits, moody music, and Halloween-inspired enchantment.
👻 Halloween Spooktacular
📅 Friday, October 24, 2025 | 📍 Red Morton Community Center, Redwood City
A family favorite featuring carnival games, a monster maze, creepy crafts, and a mini pumpkin patch with prizes.
🎃 San Carlos Halloween Walk
📅 Saturday, October 25, 2025 (evening) | 📍 Downtown San Carlos (check 2025 calendar for details)
Downtown San Carlos transforms into a festive trick-or-treat zone with costumes, decorated storefronts, and plenty of Halloween spirit.
✈️ Hiller Aviation Haunted Hangar & Halloween Activities
📅 Late October (check dates) | 📍 Hiller Aviation Museum, San Carlos
A spooky aviation twist on Halloween: haunted hangar tours, aircraft displays, and even pumpkin drops.
🍁 Burlingame Fall Fest
📅 Sunday, October 26, 2025 | 📍 Downtown Burlingame
Carnival rides, costume contests, food, and live music — a true neighborhood celebration that brings everyone downtown.
🎨 CA Artists Fall Festival
📅 Sunday, October 26, 2025 | 📍 Howard Avenue, Burlingame
Pair Fall Fest with this vibrant art fair. Local makers, painters, and crafters line Howard Avenue, turning Burlingame into an arts hub for the day.
✨ Why October 2025 Is Special
From San Mateo’s bacon & beer kickoff to Burlingame’s closing weekend festivals, October is bursting with flavor, art, and autumn energy. In between, you’ll find the Half Moon Bay Pumpkin Festival, the legendary Pumpkin Weigh-Off, and the magic of Filoli by day and night.
Add in Redwood City’s PortFest, spooky nights at Hiller Aviation Museum, and family-friendly fun in San Carlos, and you’ve got every weekend covered.
🍂 Every weekend offers something new — whether you’re chasing giant pumpkins, sipping cider under historic oak trees, or dancing in the streets of Burlingame.
