FRIENDS OF MAIN STREET
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Halloween Window Painting Contest

Picture
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. 

2025 Winning Teams!

🎃 The 2025 Spooky Windows on Main Street event was a huge success! This year, 21 businesses participated, showcasing 55 painted windows created by 100 talented students. We’re so proud of everyone who joined in the fun—and congratulations to this year's winners!​
Grade
Winning Teams
Kindergarten
Emory Rhoades & Lily Vold​
First
Colbie Dombrowski & Hazel Dixey
Second
Cali Fullerton & Serenity Ostrader​
Third
Adelynn Laurel & Talisa Kelley​
Fourth
Dylan Moodie-Kalman & Tuelee Quach​
Fifth
Kaia Galvin & Lily Gagnon​
Sixth
Gia Cadrain & Lizzy Blakeney​

​A big howl out to the Winsted Fire Department, who cleans the windows each year! 

We could not have such fun without our Main Street participating businesses:  Park Place Hardware, Northwest Community Bank, Northwest Realty, ABC Pizza, Winchester Hardware, The Gilson Cafe and Theater, The Curious Cat Bookshop, Be Under Par Performance, Friends of Main Street, Rooted Market, Andy's Attic
, Peacocks & Lilacs Thrifty Boutique, Noujaim's Bistro, Birchwater Properties, JB Appliance, Mad River Music, F & G Richards Jewelers and Railway Cafe!

​Let's not forget to thank our judg
es –
​
Andy Jones, Pam Dean, and Mark Lampognana 
 👻

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 Tuesday, October 14, 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]).

All forms must be returned to the school offices by Monday, October 20.

​Painting Day – Saturday, October 25!

Children can paint their windows on Saturday, October 25, but if they have sports or other activities that day, they’ll have until Noon on Sunday, October 26, to finish. Participating families should plan ahead and pick up paint kits and window assignments between 9 am and 2 pm on Saturday.
​
All windows will be judged starting on Sunday afternoon.
​
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 that no paint is on the sidewalk or window frame.  No SPRAYING of paint. Bring brushes (inexpensive disposable foam ones work well), a small container of water 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).

On 
Saturday, November 1, between 1:00 and 2:00 pm, each member of the ​🏆​ Winning Team will receive $10.00 (cash) at the FOMS office 

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).

2025 Halloween Window Painting Flyer.pdf
File Size: 585 kb
File Type: pdf
Download File

2025 Business Sign-up Form.pdf
File Size: 236 kb
File Type: pdf
Download File

2025 Student Sign-up Form.pdf
File Size: 123 kb
File Type: pdf
Download File

Picture
Preparing for Halloween Window Painting!
© 2026 Friends of Main Street Winsted-Winchester, Inc., PO Box 18, 398 Main Street, Winsted, CT 06098
  • HOME
  • ABOUT
    • Mission, Location & Hours
    • What We Do
    • Work, Play, Day Tripping: Winchester
    • Board of Directors
  • SUPPORT
    • Sponsors
    • Donate & Volunteer
  • EVENTS
    • Bubble & Truffles 2026
    • Restaurant Week
    • Earth Day Cleanup
    • Flowers on Main Street
    • Summer Concert Series
    • Fall Foliage Festival >
      • 25th Fall Foliage Festival
    • Fall River Cleanup
    • Halloween Window Painting
    • A Winsted-Winchester Christmas
  • CALENDAR
    • Community Calendar & THE WEEKLY Newsletter
    • Blog
  • FOOD, BREW, FUN & NECESSITIES
    • Antiques
    • Attractions
    • Food, Brew & Catering
    • Recreation & Exercise
    • Necessities
    • Salons & Personal Services
    • Shopping
  • CONTACT
  • Summer Concert Series