Halloween Window Painting Contest
October 25-26, 2025 (9:00 am)
The 43rd Halloween Window Painting Contest is set for Saturday, October 25th. The contest is open to all Winchester area students in the K-6 age group, including those attending schools out of town or homeschooled. Teams of children (2) will be out and about painting their assigned windows during the day, beginning at 9:00 am. Brew up a frightening display of ghosts and goblins! Get signed up for the contest! Forms for the Halloween Window Painting Contest will be dropped off at the K-6 school offices on Monday, October 6, and emailed to parents at Hinsdale and Pearson schools. Homeschooled/students attending out-of-town may access their sign-up form below and return completed forms to Friends of Main Street (exterior mailbox or via email to [email protected]). Each member of the Winning Teams will receive $10.00 (cash) at the FOMS office on Saturday, November 8, between 10 am to 1 pm. All forms must be returned to the school offices by Friday, October 17. “Painting Day” is Saturday, October 25, but children will have until Noon on Sunday, October 26, to complete their windows should they have sports/ activities on Saturday. Participating families must plan ahead and pick up their paint kits and window assignments between 9 am and 2 pm on Saturday. All windows will be judged starting on Sunday afternoon. The Friends of Main Street weekly online newsletter will feature some of the young students' spooky artwork (subscribe so you do not miss a local event). We always try to pair younger children with lower windows, but parents should just bring a small step stool/chair. Please limit the use of black and brown in artwork – the concentration of dark colors draws sunlight/heat, causing glass breakage. Yes - this has happened! Reminder: Parents are responsible for ensuring no paint is on the sidewalk or the window frame. Bring brushes (inexpensive disposable foam ones work well), water in a small container to rinse brushes, paper towels, and a drop cloth to keep the sidewalk clean. In the paint kit, Friends of Main Street will provide a trash bag for parents to take their trash home (please do not leave it for the shop owner). A big howl out to the Winsted Fire Department who cleans the windows each year!
We could not have such fun without our participating businesses: McGrane's On The Green, Park Place Hardware, Northwest Realty, Northwest Community Bank, Cura Café Nutrition, ABC Pizza, Mama Pho, True Value of Winchester, The Gilson Cafe and Theater, The Curious Cat Bookshop, Be Under Par Performance, Friends of Main Street, Rooted Market, Total Mortgage, Winsted News, Andy's Attic, Noujaim's Bistro, JB Appliance, Mad River Music, 2nd Home Lounge, F & G Richards Jewelers and Railway Cafe. We also thank our judges, Andy Jones, Pam Dean, and Mark Lampognana. 🎃 |
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2024 Winning Teams!The Spooky Windows on Main Street event had an overwhelming response, with 23 businesses participating (54 windows), 101 students 48 teams of two, and over 6.75 gallons of paint used. We are incredibly proud of all who participated and congratulate our winners.
The Rotary Club of Winsted started this community tradition in 1983. In 2005, Friends of Main Street was happy to continue sponsorship of this much-loved event. This is evidenced by the parents who participated as youngsters that are now bringing their own children. |
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Preparing for Halloween Window Painting!
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