The Chamber of Commerce calendar lists the Downtown Halloween Window Painting as running from October 14 to October 31. The painting itself happens in two sessions, on Friday, October 23, and Saturday, October 24, and the work has to be done by 10 a.m. Saturday. The awards are announced at noon. One week later Halloween falls on a Saturday, and the official schedule runs entirely in daylight: a City festival in the morning, then downtown trick-or-treating that ends at 5 p.m.
Put those together and Sierra Madre's Halloween is planned around two Saturdays and a few hours on each one.
Friday Afternoon and Saturday Morning Are When the Windows Get Made
The Sierra Madre Civic Club runs the contest. It says it has supported town traditions since 1944, Halloween Window Painting among them, and has raised and returned more than $400,000 to the community over that time. In September, Mountain Views News described the club as a women's nonprofit that has volunteered and raised funds for the town since its founding year.
The club's 2026 rules set out the painting weekend:
- Friday, October 23, 2:30 to 6 p.m. First painting session. Teams check in at tables in Kersting Court and get their window assignment there.
- Saturday, October 24, 7:30 to 10 a.m. Second and final session.
- Saturday, 10 a.m. to noon. Judging.
- Saturday, noon. Awards are announced in Kersting Court.
The whole weekend runs on a 10 a.m. cutoff, set by rule 13.
"ALL WINDOWS MUST BE COMPLETE AND THE SURROUNDING AREA MUST BE CLEAN BY 10:00 a.m. SATURDAY."
So by mid-morning on the 24th, the downtown stretch around Sierra Madre Boulevard has changed from storefronts with masking tape and drop cloths to a finished gallery. That gallery stays up through Halloween. If you stop by Kersting Court Friday afternoon or early Saturday, you'll see the windows being painted, which the October 14 to 31 listing doesn't mention. Applications closed in mid-October. The Civic Club's rules gave October 15 at 4 p.m. as the deadline, and the Chamber listing said October 16.
The Rules Shape What Ends Up on the Glass
The rules explain a lot about how the finished windows look. Painters are 9 to 17 years old and work in teams of two to four. At least one teammate has to live in Sierra Madre. The oldest member sets the team's age division: 9–10, 11–12, 13–14 or 15–17. Adults can't help paint. Any window with adult help is out of the running for a prize, though the club welcomes adult help with cleanup.
Some of the limits are practical, not about taste. Teams submit a color drawing with the application, and the rules ask that it avoid large areas of black or dark colors. Dark paint absorbs heat and can crack the window. That's one reason the downtown windows tend toward bright pumpkins and lighter colors over the deep-black look common elsewhere in October. The rules also turn away gory or politically motivated drawings, and every team has to use paint the Civic Club provides.
The shops stay open the whole time. Teams have to introduce themselves to the merchant before they start, keep paint off the sidewalk and building, and remember that the business will be open during and after the contest. Cleanliness is one of the judging categories. If you're shopping downtown Friday afternoon, you may be stepping around a stepladder and a drop cloth on the way in.
Last Year's Winners Show How Far the Windows Spread
Mountain Views News published the 2025 winners on November 1, 2025, and the list doubles as a map. Dozens of young artists painted windows that local businesses donated, and the winners were spread along downtown:
| Age division, 2025 | First-place window | Some other placing storefronts |
|---|---|---|
| 9–10 | #6A at Casa Del Rey | Casa Del Rey, Pax Pharmacy 2 |
| 11–12 | #30A at Pantorium | Cancer Support Community |
| 13–14 | #12A at Homework Club | Only Place in Town, Coffee jpg |
| 15–17 | #21A at Bottleshop | Syndicate |
The window numbers ran past 30 last year, and some storefronts had both an A and a B pane. That's how two teams ended up placing on the same Casa Del Rey frontage. The 2026 storefronts are handed out at check-in, so last year's list is a guide to where the windows usually are, not a promise. The Civic Club's thank-you that year said the display made "downtown a festive destination for residents and visitors alike."
Since the windows are finished by the morning of the 24th, the best time to walk them is any day that week. That gives you a full week with the gallery before the October 31 crowds arrive.
On October 31, the Official Schedule Ends at 5 p.m.
The windows set up the week, and Halloween Saturday closes it out on a daytime schedule. The City's Community Services staff report on the 2026 Hometown Halloween Festival, in the September 21, 2026 commission packet, lays out the morning block by block.
- 10 a.m. to 2 p.m., Memorial Park. The festival opens with a performance by the Sierra Madre Dance Center, which the City calls part of the event's traditional programming. The Skinny Ties follow with classic 1980s hits and Halloween favorites, sponsored by Christ Church. The rest of the morning includes a free pumpkin patch, face painting, a caricature artist, a themed photo booth and a Kid Spook Zone with inflatable games and bounce houses on the south side of the park.
- During the festival, Hermosa and Mariposa Avenues. Trunk-or-treat is new this year and runs along part of Hermosa Avenue. Food vendors set up on Mariposa Avenue.
- 2 to 5 p.m., downtown. The Chamber of Commerce hosts a business trick-or-treat to "keep the Halloween fun going after the City's Hometown Halloween Festival." Businesses that want to be a stop can sign up at [email protected].
The start time is the one detail to double-check. The header on the Chamber's festival listing says noon to 2 p.m., but the description below it and the City's staff report both say 10 a.m. to 2 p.m. If you go by the header, you'll miss the first two hours of the festival.
The handoff matters too. The festival ends at 2, downtown trick-or-treating starts at 2, and the painted windows from the weekend before line the same blocks. A family that starts at Memorial Park and heads toward downtown in the early afternoon catches all three in one walk.
The Days In Between
The week between the two Saturdays has a few anchors of its own. Sierra Madre Playhouse is staging John Patrick Shanley's Outside Mullingar with The 6th Act. The listed cast is Armin Shimerman, Kitty Swink, Liza Seneca and Michael Kirby, and performances run through Sunday, October 25. That's the day after the window awards, so the run's final weekend overlaps with the gallery's first full day. The show is part of the Playhouse's 2026 season, "Small Stage, Big World."
The Sierra Madre Public Library's September–October calendar has a pet-painting session on October 22 and an adult tabletop game night on October 27.
After October, the next date on Kersting Court's calendar is the Chamber's Sierra Madre Winter Village on Saturday, November 28. It runs noon to 5 p.m. with a holiday artisan marketplace and a snow-sledding hill, and the community tree lighting follows at 6 p.m.
I love how much of Sierra Madre's Halloween is built by its own kids and shop owners, one window and one trick-or-treat stop at a time. If you have questions about the town, or about your own plans in the San Gabriel Valley, I'm always glad to talk them through. Renee Bannoura. Let's Connect.
