San Mateo Halloween Movies, Theater, and Entertainment 2026

6 Halloween movies, theater, and entertainment in San Mateo and nearby.

Halloween events this year span San Mateo and nearby Colma, offering both ticketed and free experiences. From theatrical productions in San Mateo to an outdoor cinema experience in Colma, there's entertainment for different preferences.

If you prefer an outdoor movie, consider the Colma screening. For a more theatrical evening, San Mateo hosts unique performances.

All Halloween Movies, Theater, and Entertainment Around San Mateo

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Illustration of small costumed children and a witch on a sunny autumn lawn with pumpkins, hay bales and orange trees

Family-Friendly Fall Activities

1 of 48 Half Moon Bay Art & Pumpkin Festival Half Moon Bay

World pumpkin capital celebration featuring giant champion gourds and artisan crafts.

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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 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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Frequently Asked Questions

How do we pick age-appropriate scary movies and shows for kids in San Mateo?

Use ratings as the floor, not the verdict: a sensitive 10-year-old and a horror-curious 8-year-old need different calls. Preview the specific film's scare profile, jump scares and peril read differently than gore, and check parent-review sites for scene-level detail. Matinee family screenings of classic monster movies are the on-ramp. Agree on a mid-movie exit signal that carries no shame.

Which October weekend is best for movies and shows in San Mateo?

Flip the haunted-house logic: screenings and theater get better as Halloween approaches, with the deepest programming, marathons, shadow casts, themed pre-shows, on the final two weekends. Early October is for tickets to things that will sell out, late October is for attending them. Halloween night itself often has the best cult-screening energy of the year and lighter crowds than the Saturday.

How do we organize a group outing to a Halloween show in San Mateo?

One person books all seats in one transaction the day plans firm up, reserved-seat maps scatter latecomers, and collects money immediately via payment app. Send calendar invites with the actual arrival time, 30 minutes pre-show, not curtain time. Pick a lobby meeting spot, hand out tickets digitally in advance, and choose an after-show debrief venue within walking distance.

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