"The drawing should not have large areas of black or dark colors, as they absorb the heat and may crack the window." That line comes from the Sierra Madre Civic Club's 2026 Halloween Window Painting rules. It shows how this works. The ghosts and pumpkins that will cover downtown storefronts this month are painted right onto real merchant glass. They sit in the afternoon sun on Sierra Madre Boulevard. Kids design them, and they plan around how the glass handles heat.
Downtown is painted on the weekend of October 24. By the time the festival opens at Memorial Park, the windows have been up for a week.
Who Paints the Windows
The contest rules decide who decorates downtown. Entrants must be 9 to 17 years old on contest day and work in teams of two to four. At least one team member must be a Sierra Madre resident. Each team turns in a color drawing on letter-size white paper with its application. Teams compete in age groups of 9–10, 11–12, 13–14 and 15–17, and the oldest member sets the group.
Two rules shape how the windows look. Teams must use paint supplied by the Civic Club, and no other paint is allowed. Teams must also paint without adult help. A window that an adult helped with is out of the running for a prize. Designs should stay "in good taste," and the rules turn away gory or politically motivated drawings.
So every painted window on Sierra Madre Boulevard this year was drawn and painted by kids, and at least one of them lives in town. The Civic Club, which says it has served Sierra Madre since 1944, lists window painting among the town traditions its members support.
Friday Afternoon to Saturday Noon at Kersting Court
Everything happens at Kersting Court. The plaza sits at the northwest corner of Sierra Madre Boulevard and Baldwin Avenue, according to Colorado Boulevard. It has open seating and a stage, and Colorado Boulevard covered its rebuild as a community event space.
Teams check in at tables in the court, get their drawings back, and get their window assignments. The Civic Club rules set two painting sessions:
- Friday, October 23, 2:30 to 6:00 p.m. The after-school session, as downtown heads into the evening.
- Saturday, October 24, 7:30 to 10:00 a.m. The early session, for teams that want morning light and an empty sidewalk.
- Saturday, October 24, 10:00 a.m. to noon. Judging, as the brushes come out of the windows.
- Saturday, October 24, at noon. Awards in Kersting Court.
That Saturday morning is the best time of the season to walk downtown. The early session wraps up at 10, judging runs until noon, and awards follow in Kersting Court. If you need a reason to stay after the awards, Mother Moo is at 17 Kersting Court, right on the plaza. It's a small-batch creamery with handcrafted ice cream, baked goods and other sweets.
The Same Weekend the Playhouse Closes Its Fall Play
The painting weekend is also the last weekend of the Sierra Madre Playhouse's fall play. Outside Mullingar, by John Patrick Shanley, presented with The 6th Act, runs October 2 through 25. Performances are on Fridays, Saturdays and Sundays, so the last three days of performances are October 23, 24 and 25. The show runs 90 minutes with no intermission.
So on one weekend, the windows go up downtown and the play closes. A family could catch the Saturday awards at noon and see the play that same weekend before it ends Sunday. Check the Outside Mullingar event page for showtimes. The Playhouse calls its 2026 program "Small Stage, Big World," covering theater, music, dance, film, comedy and world traditions.
A Week With the Windows Up
The Chamber's listing for Downtown Halloween Window Painting runs from October 14 to October 31 and calls it a free youth-art tradition. Painting happens on the 23rd and 24th, so the windows are up for the last week of the month.
That week is a good time to look at the windows up close, on a weekday coffee run or an evening walk past Kersting Court. You can see what each age group did with the same blank glass, and how teams worked around the rule against big dark areas on glass that sits in the sun.
October 31 Moves From the Park to the Shops
By the time Halloween arrives, the painted windows serve as the backdrop for the day's second half. Colorado Boulevard's October 1 report lays out a schedule that starts at Memorial Park and ends at the downtown shops. Everything is free.
| Time | Where | What's happening |
|---|---|---|
| 10:00 a.m. to 2:00 p.m. | Memorial Park, 222 W. Sierra Madre Blvd. | Free pumpkin patch, spook zone, face painting, caricature artist, photo booth, food vendors |
| 10:00 a.m. to 2:00 p.m. | Hermosa Avenue | Trunk-or-treating |
| During the festival | Memorial Park | Live music by The Skinny Ties and a performance by Sierra Madre Dance Center |
| 2:00 to 5:00 p.m. | Downtown businesses | Trick-or-treating at local shops |
About the start time: the description on the Chamber's festival page and Colorado Boulevard's report both say 10 a.m. The heading of the Chamber's page shows noon to 2 p.m., so confirm with the City or the Chamber before heading over.
The 2 p.m. handoff is what makes the day work. Families leave the park, walk downtown and trick-or-treat past the windows that kids from their neighborhoods painted the weekend before. As of the October 1 report, these businesses had signed on "so far":
- Mother Moo, 17 Kersting Court. The creamery on the plaza where the windows were judged.
- M&C Collective, also known as Collective Co-op, 52 W. Sierra Madre Blvd., which houses several shops under one roof.
- Lumen Optometric, 14 W. Sierra Madre Blvd. An optometry practice offering eye exams, contact lens exams and other vision care.
- The Kensington, 245 W. Sierra Madre Blvd. A care-focused residential community on the boulevard.
- Homework Club, a tutoring and enrichment program. Its site lists both a downtown main office and a school-campus location, so check which one is taking part.
- Fables & Fancies and Seven Gables Hotel Shirley, also on the reported list.
That list was described as partial in early October, so expect more doors by the 31st. Most of the confirmed stops sit along a short stretch of West Sierra Madre Boulevard, from Lumen Optometric at No. 14 to The Kensington at No. 245, with Kersting Court in between. That's an easy walk for small legs between 2 and 5 p.m.
What Comes After the Paint
October's community calendar opened with the Sierra Madre Wine Walk on October 10. The Chamber says the event returned after a long hiatus and benefited the Sierra Madre Community Foundation.
Next on the downtown calendar is Sierra Madre Winter Village on Saturday, November 28, 2026. The Chamber is promoting a shop-small marketplace, community booths, live music, dining and a snow-sledding hill. Kersting Court has hosted that kind of shop-small afternoon before; the Chamber listed it as the site of a Small Business Saturday live-music event in 2025.
Until then, the windows stay up on Sierra Madre Boulevard. Judging ends at noon on Saturday, October 24, and the trick-or-treating ends at 5 p.m. on October 31.
If you're thinking about buying or selling a home within walking distance of Kersting Court and Memorial Park, Nichole Dunville would be glad to walk through it with you. Let's Connect.
