Half Moon Bay Pumpkin Festival: Plan Your October Coastal Trip
- 20 hours ago
- 3 min read
October Is the Best-Kept Secret on the Coastside
Most people assume Moss Beach and Half Moon Bay are summer destinations. They're missing something. October is the sunniest month of the year along this stretch of California coast — nearly 25 sunshine days on average, more than any month in summer — with temperatures in the mid-60s that feel built for layers and outdoor walking rather than heat and crowds. The coastal fog that dominates June and July mostly clears by fall, and the light in October has that low, amber quality that makes the Pacific look like it's lit from below.
The Half Moon Bay Art & Pumpkin Festival gives October a natural anchor.
The 54th Annual Half Moon Bay Art & Pumpkin Festival
The festival runs October 17–18, 2026, on Historic Main Street in Half Moon Bay — a 10-minute drive south of Moss Beach. Both days run 9am to 5pm, and the event draws hundreds of thousands of visitors over the weekend, which means getting there early and having a nearby base to retreat to makes a real difference.
The main attractions: 250-plus booths of handcrafted art, food, and fall goods; four live music stages running throughout the day; a costume contest Saturday morning at 10am near the Half Moon Bay Library; and the signature Great Pumpkin Parade at noon on Saturday, when the weigh-off champion gets a victory lap down Main Street. The Family Fun Zone hosts Pumpkin Pie Eating Contests, and pumpkin carver Farmer Mike works on-site all weekend, turning competition-sized gourds into intricate carvings that draw their own crowd.
If you want to see where the parade champion comes from, the Safeway World Championship Pumpkin Weigh-Off happens October 12 — five days before the festival opens. Growers haul in Atlantic Giants from across the country; the heaviest pumpkins routinely top 2,000 pounds. It's free to watch and genuinely remarkable, in the way that only a 2,200-pound vegetable can be.
After two full days on Main Street, 590 Stetson is about 10 minutes north up Highway 1 — room for up to 10 guests, an indoor fireplace for cooler October evenings, and a private patio to wind down before doing it again the next morning.
The Rest of the Weekend
The festival is the anchor, but it doesn't have to be the whole trip.
Fitzgerald Marine Reserve, a short walk from the house, is quieter in fall than in summer. The crowds thin out, and the tide pools are just as good — three miles of intertidal rock along a dramatic stretch of coastline, with sea stars, anemones, and hermit crabs visible at low tide. October's minus tides can be dramatic; check the tide charts and aim for an early-morning visit when the water pulls back the farthest.
The Pillar Point Bluff Trail, a 3-mile out-and-back above Pillar Point Harbor, is worth doing for the fall light alone. You get a long look south down the coast and a clear view of the wave at Mavericks from the bluff overlook. Late October is also when the first gray whales begin their southbound migration — bring binoculars and scan the horizon from the trail.
If the city calls, San Francisco is under an hour from Moss Beach. October is one of the city's best months — Fleet Week lands in mid-October, the Ferry Building's Saturday market runs year-round, and Golden Gate Park is worth the drive in fall light. The drive back down Highway 1 in the evening, with the ocean on your right, is its own kind of ending to a good day.
October at the coast rewards the people who plan for it — and the Pumpkin Festival makes the planning easy. If you're thinking about a fall coastal getaway, I'm happy to answer any questions about the area or the house — reach out anytime.
About Yvonne Yang
Yvonne Yang is the host of 590 Stetson, a veteran Silicon Valley real estate agent with nearly 23 years of experience.
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