Rock the 'Dale was supposed to happen on Sunday, September 20. Bad weather pushed it to Sunday, October 11, according to the Village's September 28 release. The mayor's September 9 community letter had it on the September calendar, and Scarsdale's fall plans were built around that date. Now the concert lands exactly one week before the 75th Annual Halloween Window Painting Contest on Sunday, October 18.
So the anniversary year of Scarsdale's oldest downtown tradition is no longer a single Sunday in the Village Center. It's now the middle of a stretch of events on the same few blocks around Chase Road, Spencer Place and Harwood Court, with the Sunday farmers market running through every week of it.
Seventy-five years of tempera on glass
The contest began in 1952. That start date comes from a 2014 Scarsdale10583 story, which also reported that the Recreation Department believed Scarsdale was the first village to run a contest like this. The numbers add up. That 2014 contest was billed as the 63rd, so this year's is the 75th.
The 2014 contest drew 149 individual entries, 117 team entries and 106 parent/child entries, for 595 participants in total. The grand prize went to Mary Cecil for "Ghoul with the Pearl Earring." Eight years later, Scarsdale10583 counted 204 contest entries plus 158 family painters. The 2022 grand prize went to Isabelle Zhu for a skeleton painting, and student musicians played alongside the painters for the first time that year, at the invitation of Friends of Music & the Arts.
The judging has a long memory too. In 2014, the volunteer judges included current and former Scarsdale residents, many of them former window painters themselves. The same story caught a lesson every first-year family learns:
"It was fun and challenging for parents and children who quickly learned that there's even an art to painting the window background."
The Village's Department of Parks, Recreation, and Conservation runs this year's contest from 9:00 AM to 4:00 PM. Students in grades 3 through 10 can compete if they live in Scarsdale or on Garth Road, attend a Scarsdale school, or attend Immaculate Heart of Mary School. A separate family option is open to children painting with parents, teens past 10th grade, and adults. Fees are $30 for an individual, $40 for a pair, and $40 for a family entry of up to five people. Registration is at scarsdale.gov/recreation, space is limited, and the notice says to register early but doesn't give a deadline. The registration notice went out on September 28.
The 2026 notice doesn't spell out how windows are assigned, how judging works or what happens if it rains. Last year's rules are the only guide. In the prior year, windows went first-come, first-served, and location requests weren't accepted. The 2025 winners list was split into 3rd grade, 4th grade, grades 5–6, grades 7–8 and grades 9–10. Awards included first, second and third place, Most Comical, honorable mentions and an overall Grand Prize. Treat all of that as last year's setup until the Village says otherwise.
October on the same few blocks
On a normal Sunday, Destination Scarsdale sets up on Chase Road outside the Post Office. The farmers market runs from 8:30 AM to 1:30 PM, and Scarsdale Business Alliance activations run from 9:30 AM to 12:30 PM. The mayor's September letter says the market continues every Sunday through November 22. October adds a bigger event almost every weekend on those same blocks.
| Date | Village Center event | What changes downtown |
|---|---|---|
| Sun., Oct. 11 | Rock the 'Dale, 10:00 AM–2:00 PM; SBA calendar also lists Non-Profit Day | Chase Road from Popham Road to Christie Place, Spencer Place, Boniface Circle and Harwood Court close 6:00 AM–3:30 PM |
| Sun., Oct. 18 | 75th Halloween Window Painting Contest, 9:00 AM–4:00 PM; SBA Halloween Window Painting/Family Fun Day | Storefront windows become the canvases |
| Sun., Oct. 25 | SBA Member Activation at the market | Regular market Sunday with an SBA activation |
| Fri., Oct. 30 | Halloween Parade | Time and route not yet published |
The Rock the 'Dale lineup is The Sawtelles, Hot Lunch, The Modtones, Louise in Trouble and The Del Bocas. The day also includes food stations and lunch specials from Village restaurants, the Down to Earth Farmers Market, art projects and face painting. Free Sunday parking is available in the Christie Place Garage and on nearby streets outside the market area.
Spencer Place is on the closure list, and that matters more this year because of Capretta. Z Hospitality Group's modern Italian restaurant opened September 15 at 57 Spencer Place, in the former Akai space. Mayor Justin Arest, Deputy Mayor Dara Gruenberg and Trustee Tim Foley cut the ribbon on September 22. On October 11, Capretta's block is inside the festival footprint, less than a month after it opened. Scarsdale Wine Merchants is also in a new spot. It moved from Depot Place to a larger shop on East Parkway, and owner Kristie Petrullo Campbell has said weekend tastings are planned.
The parade closes out the run. Last year's version is the best guide, but this year's details haven't been published. In 2025, Scarsdale Parks and Recreation held it at Chase Park. Entertainment started at 3:30 PM, lineup was at 3:45 PM, the route made a lap around Harwood Court, and a bubble show and a magic show followed. Registration was required. Scarsdale10583's coverage described very young children in costume trick-or-treating their way around Harwood Court while Recreation staff handed out treats. Harwood Court is also on the October 11 closure list, though the Village hasn't said whether this year's parade will use the same loop.
The rest of the month, around the Village Center
The Village Center events sit inside a longer list of fall programs, and a few of them land on the same weekends:
- Sat., Oct. 3: Scarecrow Making Hayday at the Pool Complex, 11:00 AM–2:00 PM, with scarecrow-making, food, a DJ and line dancing, face painting, crafts and animals from Weinberg Nature Center. The same morning, Scarsdale Public Library hosts a Halloween Concert with Armelle from 10:30 to 11:15 AM. Registration was required, and it had a waitlist as of September 30.
- Sun., Oct. 4: Weinberg Nature Center's family Apple Cider Festival with live owls, 2:00–3:30 PM.
- Thu., Oct. 15: "Trivia – Halloween and Horror" for adults and seniors at the library, 3:00–4:30 PM. Registration is required, and players compete individually rather than in teams.
- Sat., Oct. 24: A children's Halloween Drop-In Craft at the library, 9:30–11:30 AM, with no registration, as space and supplies allow.
- Thu., Oct. 29: The library's Children's Spooky Soiree, 6:00–7:30 PM, with crafts, a photo area and costumes encouraged. No registration needed. The same evening, Greenburgh Nature Center hosts an adult Spooky Trivia Night at 6:30 PM.
Plan a little extra time for the library programs. The privately funded "Library in the Park" grounds project broke ground June 29, and the library says construction will continue into winter and may limit parking. When it's done, the project adds an outdoor pavilion and plaza with about 60 seats and keeps all 114 existing parking spaces.
What carries into November and December
The window paintings come down, but the Sunday setup on Chase Road keeps going. The farmers market runs through November 22. On November 16, the library and a Weinberg naturalist hold children's and adult Apple Cidering sessions with a traditional cider press in the Scott Room. Light the 'Dale follows on December 4.
Before October 18, the only open question is registration. The Village hasn't posted a deadline and says space is limited. In 2022, 362 entrants and family painters signed up, so a family hoping for a window this year should register at scarsdale.gov/recreation soon.
Twenty years of Octobers in Scarsdale have taught Daniel Mckeon how much the Village Center calendar shapes a street, from which blocks close on a Sunday to where the parade loops. If you're wondering how the area around Chase Road and Spencer Place fits your plans for the years ahead, schedule a consultation and we'll walk through it together.
