Home » *Top Pick*, Community, Halloween, In Person, Outdoors

2026 Pillar Point Harbor Costumed “Witch Paddle” on Kayaks + Paddle Boards (Half Moon Bay)

Coastside Buzz

The San Mateo County Harbor District hosts a free Halloween-themed paddle at Pillar Point Harbor in Half Moon Bay. Participants can paddle in swimmable costumes and must wear a life vest or PFD. Spectators are also welcome, and the paddle is followed by a Trunk or Treat event in the harbor at 2 PM.

Original Event Description:
_San Mateo County Harbor District Hosts 2026 Pillar Point Halloween Witches Paddle Half Moon Bay Witch Paddle is Sunday, October 25 at 10 AM. Come paddle with us or just come out to watch. Wear a costume you can swim in and a life vest over. The event is free and followed by Trunk or Treat in the harbor at 2 PM_

Text extracted from provided image:
PILLAR POINT
HARBOR WITCH PADDLE
SPONSORED BY
THE HARBOR DISTRICT
OCT 25TH | 10 AM
ALL COSTUMES WELCOME
BUT NEEDS TO BE
SWIMMABLE
Need to rent a paddleboard
or Kayak?
#HMBKAYAKCO has got you, rent early
MANDATORY
PFD/Life vests
or risk being
ticketed
2 JOHNSON PIER IN THE PILLAR POINT HARBOR
HALF MOON BAY LAUNCH SPOT
The HMB Paddle Club will be taking pictures
so summon your spirit and prepare to GLIDE!

Disclaimer: Please double check event information with the event organizer as events can be canceled, details can change after they are added to our calendar, and errors do occur.


Cost: FREE*
*Costumes are welcome but must be swimmable. A PFD/life vest is mandatory. Paddleboard and kayak rentals may be available through #HMBKAYAKCO; rent early.
Categories: *Top Pick*, Community, Halloween, In Person, Outdoors
Venue: Pillar Point Harbor
Address: 2 Johnson Pier, Half Moon Bay, CA 94019

Other Events on This Day

Sunday, October 25, 2026

10:00 am   SFMOMA’s “Free Family Day” Free Museum Day  FREE*
*Free for up to four adults accompanying each visitor 18 and younger.
10:00 am   Football Sundays: Outdoor Big Screen NFL Games + Lawn Fun (Thrive City)  FREE
11:00 am   2026 “World of Dumplings” Festival at SF’s Ferry Building  FREE
11:00 am   Bark at Spark: Howl-O-Ween (SF)  FREE*
*RSVP Requested but not Required
11:00 am   SF’s “World of Dumplings” 2026: Free Community Food Fest (Ferry Building)  FREE
11:00 am   SF’s Free “World of Dumplings” Festival at the Ferry Building  FREE*
*Free admission for all ages. Advance registration is encouraged but not required. Food and beverages are available for purchase directly from participating vendors. No purchase or donation is required to attend.
12:00 pm   Golden Gate Park “The Whale’s Tail” Beer/Wine Garden + Live Music (Summer 2026)  FREE*
*Free admission and entertainment for all ages. Dogs and bikes welcome. Food and beverages available for purchase.
12:00 pm   SF’s “Sundays at the Beach” Free Yoga Day (Great Highway)  FREE
12:00 pm   SF Music Day 2026: 20+ Free Live Concerts (San Francisco War Memorial)  FREE
12:00 pm   “Free Oakland Up” Market: Shop for Free Treasures (Every Friday-Sunday)  FREE*
*All outdoor items are free; one free indoor item per person per day, additional items for donation. Some plants and select treasures for sale.
2:00 pm   2026 “Howl-O-Ween” Pet Parade at City Center Bishop Ranch  FREE
5:00 pm   Free Halloween “Trunk Or Treat” Party w/ Bounce Houses (SF)  FREE
6:00 pm   “HellaSecret” Speakeasy Comedy Show & Cocktail Night (Oakland)  FREE*
*Free with RSVP
6:00 pm   $10 Off Tix: SF’s “Terror Vault” 1874 Halloween Haunt (2026)  $10 Off*
*Use code FUNCHEAP for $10 off tickets, but only 50 discount tickets available per date
7:00 pm   Free Sunday Comedy Night in Downtown SF  FREE*
*Exclusive free tickets with Eventbrite RSVP. Otherwise $20-25 at door. Please note like most comedy clubs, there is a two drink minimum per person
< Saturday, October 24 Monday, October 26 >