San Mateo Family-Friendly Fall Activities 2026

47 family-friendly fall activities in San Mateo and nearby.

The popular Pumpkin Festival in Half Moon Bay highlights local Halloween celebrations. For families closer to home, consider events happening right in San Mateo.

San Mateo and surrounding towns offer numerous family-friendly Halloween activities, from pumpkin patches to community gatherings. Decide if you prefer a ticketed experience or a free community event.

All Family-Friendly Fall Activities Around San Mateo

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Illustration of a Halloween gathering at dusk with a smiling ghost, costumed figures, glowing jack-o'-lanterns and lights

Food, Drink, and Parties

1 of 27 Fairmont Hotel San Francisco MEGA Halloween Party San Francisco

Five themed rooms and 10 DJs for a mega Halloween party

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 Illustration of a small cottage with glowing windows, ghosts, jack o'lanterns and black cats under a full moon at dusk

Haunted Experiences

1 of 11 The Great Hauntway San Francisco

A community-powered, car-free Halloween celebration at the beach.

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 Illustration of a pumpkin character and a ghost performing on a lit stage with red curtains before a crowd at night

Movies, Theater, and Entertainment

1 of 6 Chamber Music Stowe Fall Concert - Schubertiade II Stowe

Live performance of Schubert's Cello Quintet in the Mozart Room.

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 Illustration of a Halloween town at twilight with glowing houses, jack o lanterns, ghosts, and a witch flying past the moon

Unique & Unusual

1 of 10 Safeway World Championship Pumpkin Weigh-Off Half Moon Bay

Growers compete for prizes with massive, Volkswagen-sized pumpkins.

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See all trunk-or-treats, pumpkin patches, and kid-friendly events nearby.

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San Mateo Halloween events map - Click to view interactive map

Frequently Asked Questions

How long should we plan for a family farm visit near San Mateo?

Two to three hours covers the core loop, animals, maze, hayride, picking, snack, before under-6 stamina collapses; four hours only works with a real lunch break in the middle. Plan the exit before the meltdown, not after: leave one activity still wanted so the day ends on a high. Add 30 minutes for peak-Saturday parking and checkout lines.

How do we prep for a corn maze with kids in San Mateo?

Closed shoes that can get dirty, water, and a bathroom stop before entering are the big three. Pick the short family maze over the flagship one for under-8s; a full maze runs 45-90 minutes and patience dies at minute 30. Photograph the maze map at the entrance, agree that kids stay within arm's reach at junctions, and go before dusk on your first trip.

Which weekend is best for family Halloween events in San Mateo?

The first weekend of October has full activities and the thinnest crowds; the two weekends before Halloween are wall-to-wall wagons. If you want the buzz, go peak; if you want photos without strangers in them, go early. Late September often means opening deals. For trunk-or-treats and costume parades, the weekend before Halloween is usually the only option, so book patches around it.

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