Halloween is on a Saturday in 2026. In San Carlos, that moves most of the organized events to the day before. The Goblin Walk, the Spooky Streets winners, a free costume party at Devil's Canyon and the city's first adult Halloween pickleball tournament all fall on Friday, October 30. Saturday the 31st has one scheduled event, a helicopter dropping a pumpkin over Skyway Road at noon. After that the afternoon and evening belong to the blocks.
So the town's Halloween this year really spans two days, run by two different sets of people. The schedule below follows that split, starting with the busiest day.
Friday the 30th Holds Nearly All the Official Events
The City of San Carlos lists the Goblin Walk for Friday, October 30, from 4:00 to 5:30 p.m. on Laurel Street between San Carlos Avenue and Arroyo Avenue. It's for children 7 and under with an adult, who trick-or-treat at businesses showing a Goblin Walk sign. The first 600 kids get a trick-or-treat bag at the Parks & Recreation tent or from any Goblin Walk volunteer. In a normal year the Goblin Walk is the little-kid warm-up before the real night. This year it lands on a Friday afternoon, the day before Halloween.
That Friday fills up from morning to evening:
| Time | Event | Where | Who it's for |
|---|---|---|---|
| 9:00 a.m. to noon | Adult Halloween Pickleball Tournament, the first one the city has held | San Carlos Youth Center | Adults |
| 11:00 a.m. to 12:30 p.m. | Halloween Cookie Decorating, free, costumes welcome | City Active Adults program | Active Adults |
| 4:00 to 5:30 p.m. | Goblin Walk | Laurel Street, San Carlos Ave to Arroyo Ave | Kids 7 and under with an adult |
| 4:00 p.m. on | Halloween Boo Bash, free admission | Devil's Canyon Brewing Co., 935 Washington St. | All ages listed as welcome |
| During the day | Spooky Streets winners announced | City website and Parks & Rec social channels | Everyone |
The pickleball tournament was announced in the city's September Parks & Recreation newsletter as a first for San Carlos. According to a Patch calendar listing, the Devil's Canyon Boo Bash starts at 4 p.m. with a costume contest, live music and food trucks. It starts at the same time as the Goblin Walk. A family with a 5-year-old and an older sibling could do Laurel Street first and get to Washington Street while the party is still going.
The Seven Days Before Friday
Friday is the peak, and the week leading up to it is busy too.
- Friday, Oct. 23. Devil's Canyon holds Whimsy Market: Witches & Brews from 4:00 to 9:00 p.m., a seasonal market with artisan vendors, tarot readings, food trucks and costumes encouraged. It's also the deadline to enter the 2026 Spooky Streets decorating contest, according to the city's community events page. The Haunted Hangar opens the same day at Hiller Aviation Museum.
- Saturday and Sunday, Oct. 24 and 25. Hiller runs Halloween Paint-A-Plane both mornings from 10:00 a.m. to noon, alongside the decorated gallery and the "Great Pumpkin" Scavenger Hunt.
- Monday, Oct. 26. The city's Generation Buddies program holds Halloween Bingo & Ring Toss from 4:00 to 6:00 p.m. The program page lists a $5 fee.
- Thursday, Oct. 29. Hiller's Trunk or Treat runs from 5:00 to 7:00 p.m. That's the evening before the Goblin Walk. For families with young kids, Thursday, Friday and Saturday morning can each hold a different costumed outing.
The Hangar's own page gives two different end dates. The heading says October 23 through October 31, and the event details run to November 1. Anyone planning a visit on Sunday the 1st should check Hiller's calendar first.
Saturday Morning Is on Skyway Road
On Halloween itself the city's calendar is mostly empty, and the one scheduled event is out by the airport. Hiller's Pumpkin Drop runs from 10:00 a.m. to noon on Saturday, October 31, at 601 Skyway Road. A helicopter drops the pumpkin at noon, and the event is included with museum admission. The Haunted Hangar calls the morning its Halloween Kid's Festival, with aircraft checkouts, cockpit exploration and glider and helicopter building on offer that weekend.
Hiller's general information page lists these admission prices:
- Adults: $23 at the door, $24 online
- Seniors 65 and older: $15 at the door, $16 online
- Youth ages 4 to 17: $15 at the door, $16 online
- Free: children 3 and under with a paid adult, museum members, and active military
Members get into the Haunted Hangar display free. Regular hours are 10 a.m. to 5 p.m., but the museum warns that special events can change hours. Parking in the museum lots is free. With the drop at noon, families can be back across the highway and home by early afternoon, well before trick-or-treating.
From Noon On, the Neighborhoods Run Halloween
San Carlos's best-known Halloween tradition isn't on any city calendar. Eucalyptus Avenue has drawn trick-or-treaters for decades, and the street's displays are put on by the people who live there. In 2018 the student paper Scot Scoop reported that thousands of children came to Eucalyptus Avenue on Halloween night. With the crowds, a drive from one end of the street to a home could take half an hour. The city does manage traffic on the street in December for the resident-organized holiday lights, and says plainly that the lights are not a city event. No traffic plan or closure for Eucalyptus Avenue has been announced for Halloween 2026.
The tradition has spread to nearby streets. The San Mateo Daily Journal profiled the "Pirate House" on Brittan Avenue, near Eucalyptus. The homeowners there have decorated for years, and the paper reported that trick-or-treaters come "in droves."
Elsewhere in town, the Spooky Streets contest gives a rough map of who goes all out. The 2026 winners come out on Friday, October 30. In the meantime, these were the city's 2025 winners:
- Best Overall: 124 Devonshire Blvd.
- Scariest: 132 Highland Ave.
- Best Door: 1339 Geneva Ave.
- Honorable Mention: 111 Palm Ave.
- Honorable Mention: 128 Brook Street
The 2025 list shows decorating effort spread across San Carlos, from Devonshire to the Highland and Palm area. Since the new list comes out Friday, families have a day to work any 2026 winners into Saturday's route.
Sunday Morning, and the Next Two Dates on the Calendar
Sunday, November 1, Laurel Street is back to normal. The San Carlos Farmers' Market runs every Sunday from 9 a.m. to 1 p.m., and the operator says it's open year-round except on Art & Wine Faire weekend, which was October 10 and 11 this year. Some of the layout is newer than people may remember. A May 2026 city update said booths were moved away from the curbs, vendors expanded into the Wheeler Plaza parking lot, Cherry Street reopened to traffic and parking, and seating, umbrellas and games were added.
Laurel Street hosts the next two community events of the season:
- Diwali Downtown on Saturday, November 14, 11 a.m. to 2 p.m. The Adult Community Center has its own Diwali gathering on Friday, November 6, 11 a.m. to 12:30 p.m., with registration required.
- Night of Holiday Lights on Friday, December 4, 5 to 8:30 p.m., on Laurel Street between San Carlos Avenue and Cherry Street. The main stage is on Cherry, and the city lists snow, holiday performances and family activities.
Like the Goblin Walk, the holiday lights fall on a Friday this year, so downtown's December evening comes at the start of the weekend.
If your household is juggling a week like this one with a move, a listing or just a house you're getting ready for the holidays, timing is the part Debbie Livingston plans for. Let's connect. Whether you're starting a home search or want a free valuation before the year ends, she can map out the steps around the dates your family already has on the calendar.
