On the morning of Sunday, October 18, last year's Grand Prize winner was back at work on the window at Chopt. Up and down the Village, kids taped off their glass and rolled on a background of paint mixed with Bon Ami cleanser. Once that dried, they started on the actual drawings. That's how Scarsdale10583 described the scene in its report on the 75th Halloween Window Painting event.
More than 500 painters turned out that day. In 2025 the Recreation Department counted 330. So the windows you walk past in this last week of October make up the biggest outdoor art show Scarsdale has had in years. It also has an expiration date that no one posts.
The paint is made to come off
The Bon Ami in that background mix is there to make the paint stick. The Village's 2024 Family Rules say it thickens the paint, helps it adhere and keeps it from flaking. The paint only has to last a short time, though. When the Recreation Department announced last year's winners, Scarsdale10583 told readers to "take a walk today and see the work before it's washed off the windows." That story ran on October 23, 2025, four days after the paint went up.
The Village doesn't publish a removal date. Each merchant decides when to wash its own glass. As a result, the show doesn't close all at once. Windows go dark one storefront at a time, and by the week after Halloween you're looking at whatever is left. From Thursday, October 29, through Halloween, you're in the last few days when most of the 2026 windows should still be up.
The count dropped, then came back
The 2026 turnout matters more once you see the longer history. The Scarsdale Inquirer covered the contest on November 3, 1977, in a story you can still read in the Hudson River Valley Heritage newspaper archive. That year drew "the largest participation ever," with more than 650 kids in grades 3 through 10 painting more than 400 windows.
| Year | Painters | Where the windows were |
|---|---|---|
| 1977 | Over 650 | The Village, Heathcote, the Golden Horseshoe |
| 2025 | 330 | Downtown, Five Corners, the Golden Horseshoe, Scarsdale Avenue, Garth Road |
| 2026 | Over 500 | The Village, Garth Road, Palmer Avenue, the Golden Horseshoe |
The 2025 and 2026 counts are a little different from 1977's because adults and older teens can now join in. The Village's 2026 listing opens the judged contest to kids in grades 3 through 10 who live in Scarsdale or on Garth Road, attend a Scarsdale school, or attend Immaculate Heart of Mary School. A separate Family Window Painting option covers parents, teens past 10th grade and adults who want to take part. Scarsdale10583 spotted some of those adults this year "dabbing paint onto the windows en plein air."
The year it all started is hard to pin down. The Village calls 2026 the 75th annual contest, which would put the first one in the early 1950s if it has run every single year. But the 1977 Inquirer story already described the contest as "an event that has spanned three decades in Scarsdale." Either way, three generations of Scarsdale kids have done this.
The map is wider than downtown
The table above also shows how far the windows travel. In 1977 the paint covered the Village, Heathcote and the Golden Horseshoe. In 2025 it reached Five Corners, Scarsdale Avenue and Garth Road. This year Scarsdale10583 reported painters "on Garth Road, on Palmer Avenue and in the Golden Horseshoe late into the afternoon," in addition to the Village.
That spread is the main thing to plan around. If you only walk through downtown, you'll miss a real share of the 2026 work. Parents felt the same pull on painting day. One mother told Scarsdale10583 that her three kids were painting in three different spots, and that moving the kids and the paint around town took the whole day.
A practical order for seeing all of it:
- Start in the Village. It has the most windows close together, and that's where the Business Alliance's kids' activities ran next to the Farmers Market on painting day. Chopt, where last year's Grand Prize winner painted this year, is a good first stop.
- Drive to the Golden Horseshoe. It has been part of the contest since at least 1977.
- Add Palmer Avenue and Garth Road. Both were active in 2026. The Garth Road windows tie in with the contest's eligibility rule for Garth Road residents.
Weekday afternoons work well because the shops are open and the glass is lit from inside as it gets dark.
What the judges were looking at
Judges reviewed the windows on Monday, October 19, and Scarsdale10583 said the results would be posted later that week. Look for the 2026 winners list on Scarsdale10583 and on the Village's recreation pages. Then walk the winning windows while they're still up.
The format has stayed close to what the 1977 Inquirer described. The 2022 sign-up notice on Scarsdale10583 explained that kids paint solo or in pairs across five grade bands: 3rd, 4th, 5th and 6th, 7th and 8th, and 9th and 10th. Entries are judged on artistry, originality and humor. Family windows are not judged. The Village's 2024 winners sheet lists first, second and third place, Most Comical, honorable mentions and a Grand Prize, with separate individual and pair divisions.
Humor has always been part of the judging. In 1977 every one of the six groups got a "most comical" award next to its top three. The Chamber of Commerce supplied the store windows and the awards, and the Grand Prize came with $100 in cash, won that year with a window at Arcade Stationers. The recognition outlasts the paint, too. A 2019 Village notice invited winners to an awards ceremony where their work was shown on a large screen and each got a trophy or certificate.
Friday is the last big day
The window walk lines up with the last organized events of the Scarsdale Halloween season. Walk the windows on Thursday, October 29, or Friday, October 30, and you're already set up for the parade.
Thursday, October 29. The Nature Center at Greenburgh hosts Spooky Trivia Night at 6:30 p.m. for adults 18 and over. Details are on the Nature Center's event calendar.
Friday, October 30. The Recreation Department's annual Halloween Parade starts at 3:30 p.m., as Deputy Village Manager Emily Giovani announced at the trustees meeting covered by Scarsdale10583. The Scarsdale10583 calendar lists it in Scarsdale Village from 3:30 to 4:30 p.m. The 2026 route hasn't been announced. Last year the Village's 2025 parade notice had entertainment at Chase Park starting at 3:30, lineup at 3:45, and a parade that made a lap around Harwood Court. Treat that as last year's plan until the Recreation Department posts this year's.
Through Saturday, October 31. The Scarsdale Public Library's Children's Hallow-Read Challenge runs every day through Halloween.
If you want dinner after a Village loop, two newer spots are a short walk from the painted windows. Capretta, an Italian restaurant from Z Hospitality Group, opened on September 22 where Akai used to be. It's at 57 Spencer Place, according to LoHud's fall restaurant roundup. Scarsdale Wine Merchants has moved from Depot Place to a bigger space on East Parkway, and Scarsdale10583 reported that it planned weekend tastings.
After Halloween, the windows will start getting washed one shop at a time, and the next set won't show up until October 2027.
Andrew Rogovic grew up just over the line in Rye Brook and coaches youth sports around here, so traditions like this one feel like home. If your family painted a window this year, or you have a story about one from years back, he'd like to hear it. And if you'd like to know what your own home is worth, you can request a free home valuation through Andrew Rogovic.
