Top 7 San Mateo County Halloween 2026 Family Outings: Half Moon Bay and Menlo Park. San Mateo County earns its reputation as the Bay Area’s pumpkin heartland in October. Half Moon Bay draws families to pumpkin weighing, farms and one of the country’s great harvest festivals, while Menlo Park supplies a city-run parade, candy walk and swimming-pool pumpkin events for residents farther inland. These seven recommendations distinguish seasonal farm visits from truly Halloween-specific neighborhood activities.

Editorial review: October 10, 2026. Dates and ticket rules can be revised, and weather may affect outdoor events. This is an editorially selected guide, not a reader-voted list; visit official organizer pages before making travel purchases.

Halloween and fall 2026 at a glance in San Mateo County

Event / attraction Where 2026 schedule
54th Half Moon Bay Art & Pumpkin Festival Half Moon Bay — Main Street Saturday–Sunday, October 17–18, 2026, 9 a.m.–5 p.m.
Lemos Farm Pumpkin Patch Half Moon Bay — 12320 San Mateo Road Daily in October 2026, typically 9:30 a.m.–5 p.m.
Halloween Hoopla Parade and Carnival Menlo Park — downtown Santa Cruz Avenue to Fremont Park Saturday, October 24, 2026
Pumpkin Splash at Belle Haven and Burgess Pools Menlo Park — Belle Haven Pool / Burgess Pool Sunday, October 25, 2026
Trunk-or-Treat — City of Menlo Park Menlo Park — official venue to be confirmed Wednesday, October 28, 2026
Farmer John’s Pumpkin Farm Half Moon Bay — 850 North Cabrillo Highway Daily during the October 2026 pumpkin season, 9 a.m.–6 p.m.
Safeway World Championship Pumpkin Weigh-Off Half Moon Bay — IDES Grounds, 735 Main Street Monday, October 12, 2026, from 7 a.m.

Our 7 family-friendly Halloween and harvest picks

1. 54th Half Moon Bay Art & Pumpkin Festival

Location: Half Moon Bay — Main Street. 2026 dates: Saturday–Sunday, October 17–18, 2026, 9 a.m.–5 p.m..

The county’s signature harvest celebration features giant-pumpkin spectacle, a costume contest, pumpkin art and street entertainment. The official festival confirms the dates and daytime hours, and its schedule helps families prioritize a morning arrival. Budget for crowded roads and paid food or merchandise, even if enjoying the festival itself is inexpensive.

Visit the organizer or 2026 local event listing →

2. Lemos Farm Pumpkin Patch

Location: Half Moon Bay — 12320 San Mateo Road. 2026 dates: Daily in October 2026, typically 9:30 a.m.–5 p.m..

A ticketed farm playground with pumpkins, train and hay rides, pony experiences, a petting zoo and seasonal attractions. The operator’s 2026 calendar lists September 5–November 15 for the broader fall season, with daily October hours. Buy timed passes ahead during busy weekends; some individual activities cost extra.

Visit the organizer or 2026 local event listing →

3. Halloween Hoopla Parade and Carnival

Location: Menlo Park — downtown Santa Cruz Avenue to Fremont Park. 2026 dates: Saturday, October 24, 2026.

Come costumed for an easy neighborhood parade, treats from downtown merchants and games at Fremont Park. The city confirms the 2026 date in its Halloweek program. This is a strong choice for Peninsula families seeking a low-friction Halloween experience away from Coastside festival traffic.

Visit the organizer or 2026 local event listing →

4. Pumpkin Splash at Belle Haven and Burgess Pools

Location: Menlo Park — Belle Haven Pool / Burgess Pool. 2026 dates: Sunday, October 25, 2026.

Trade a muddy pumpkin field for a supervised pool full of floating pumpkins. The city says its ticket includes a pumpkin, decorations, a goodie bag and swim time, with separate pool sessions. Register for the correct pool and follow water-safety rules; do not rely on last year’s price or last year’s session times.

Visit the organizer or 2026 local event listing →

5. Trunk-or-Treat — City of Menlo Park

Location: Menlo Park — official venue to be confirmed. 2026 dates: Wednesday, October 28, 2026.

The final part of the city’s 2026 Halloweek programming is a car-to-car candy celebration with decorated trunks and music. The city describes free trick-or-treat bags for participants. Check the updated municipal event page for time and location before traveling: published Halloweek overview provides the date but not every on-site detail.

Visit the organizer or 2026 local event listing →

6. Farmer John’s Pumpkin Farm

Location: Half Moon Bay — 850 North Cabrillo Highway. 2026 dates: Daily during the October 2026 pumpkin season, 9 a.m.–6 p.m..

A refreshing no-admission-fee option for families who simply want to select pumpkins at a coastal working farm. The operator says parking and entry are free and leashed dogs are welcome; pumpkins are purchased separately. This is an easy alternative to a large ticketed play farm.

Visit the organizer or 2026 local event listing →

7. Safeway World Championship Pumpkin Weigh-Off

Location: Half Moon Bay — IDES Grounds, 735 Main Street. 2026 dates: Monday, October 12, 2026, from 7 a.m..

For a behind-the-scenes look at the festival’s central obsession, watch giant pumpkins arrive for an official weigh-off. It is a real agricultural competition, not a candy distribution event. The 2026 festival schedule confirms the date and morning start; plan an early day and follow spectator access rules.

Visit the organizer or 2026 local event listing →

How to plan your family outing

Half Moon Bay can be congested during October 17–18’s festival; don’t expect short drives between multiple coastside stops on those two days. Menlo Park’s 2026 Halloweek dates are October 24, 25 and 28; some cached city pages still display the 2025 dates, so use the updated current Halloweek source.

Check hours, accessibility, costume policy, age limits, weather updates and ticket availability. Some stops are daytime harvest venues rather than Halloween-night trick-or-treat events, and some have admission charges or add-on fees.

Explore California Halloween 2026 by county: See California58’s statewide Halloween events and family travel directory for the growing collection of published county guides.

More California58 county guides

Need other activities? Explore our San Mateo County year-round travel guide. Continue exploring our Halloween 2026 county series:

More travel planning: See what else California offers at OptionTrip.com.

Sources and 2026 organizer calendars

By California58 Editorial Desk. Cover image: illustrative seasonal stock photo, Taylor Foss / Unsplash, not a photograph of an October 2026 event. OptionTrip content is a clearly labeled travel-planning promotion.

Explore San Mateo County beyond Halloween

For county-specific communities, public services and local knowledge, visit the San Mateo County reference profile. You can also browse all California58 travel guides. Halloween 2026 events are seasonal and may change; check each organizer’s current calendar before traveling.

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