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Spooky Windows on Main Street this Halloween

11/11/2021

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Early Saturday morning on October 23rd, sidewalks filled with teams of K-6 young Winchester students brewing up frightening displays of ghosts and goblins all along Main Street for the 39th Halloween Window Painting Contest!

A total of 41 downtown windows were painted by 38 teams of two and three “solo” painters – 79 young artists in all  –  making more memories for everyone this Halloween!
 
Friends of Main Street and the Winsted Fire Department are excited to announce the 2021 Halloween Window Painting winners, by grade! 
​
  • Kindergarten:  Jaxon Picard & Robert Wagner
  • First:  Alexa Hudak & Skylar Blades
  • Second:  Caroline Cardillo & Kendall Wesolowski
  • Third:  Iris O’Connor
  • Fourth:  Makayla DeSanti (Gr. 4) & Alana DeSanti (K)
  • Fifth:  Callan Jeannette & Gracelynn Miner (homeschooled)
  • Sixth:  Giannah Mitchell & Cameron Picard
  • Honorable Mention:  Gabby Pardue (Gr. 3) & Emmalyn Wall (K)

A big howl out to the 16 participating businesses: 
​Northwest Realty, ABC Pizza, Mama Pho, Laurel Lanes, True Value, Padre’s, Rooted Market, Friends of Main Street, Noujaim’s Bistro, Laurel City Coins, Keefe Land Surveying, JB Appliance, F & G Richards Jewelers, Valley Thrift Shop, Salvation Army, and Little Red Barn Brewers.  
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© 2025 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
    • Donate & Volunteer
    • Sponsors
  • EVENTS
    • Bubble & Truffles 2025
    • Restaurant Week
    • Earth Day Cleanup
    • Flowers on Main Street
    • Summer Concert Series
    • Fall Foliage Festival >
      • 25th Fall Foliage Festival
      • Sponsor Opportunities
      • Vendor Application
    • 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
    • Necessities
    • Recreation & Exercise
    • Salons & Personal Services
    • Shopping
  • CONTACT