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School Open
Dismissal: 3:30 PM
Next 7 Days
October 2026
Coming Up
School Breaks
Holidays (No School)
The Winchester School District school calendar for the 2026-27 school year runs from Thursday, August 27, 2026 to Tuesday, June 8, 2027 in Winsted, Connecticut.
- •4 scheduled breaks and 7 holidays throughout the year
- •Spring break: Apr 12 – Apr 16
- •Winter break: Dec 24 – Dec 31
Winchester School District starts school 375 days later than most Connecticut districts. Winter break starts 365 days later than the most common Connecticut schedule.
Download the iCal file above to sync all Winchester School District dates with your phone or computer.
Frequently Asked Questions
Is Winchester School District school open today?
Yes, Winchester School District is open today. Check the weekly calendar above for upcoming school days and closures.
When is the next day off for Winchester School District?
The next day off is Monday, October 12, 2026 for Holiday- No School.
When is the first day of school for Winchester School District?
The first day of school for Winchester School District in 2026-27 is Thursday, August 27, 2026.
When is the last day of school for Winchester School District?
The last day of school for Winchester School District in 2026-27 is Tuesday, June 8, 2027.
When is spring break for Winchester School District?
Spring break for Winchester School District is Monday, April 12, 2027 to Friday, April 16, 2027.
When is winter break for Winchester School District?
Winter break for Winchester School District is Thursday, December 24, 2026 to Thursday, December 31, 2026.
When do students go back to school after winter break?
Students in Winchester School District return to school after winter break on Friday, January 1, 2027. Winter break ends on Thursday, December 31, 2026.
When is Thanksgiving break for Winchester School District?
Thanksgiving break for Winchester School District is Wednesday, November 25, 2026 to Friday, November 27, 2026.
How do I add Winchester School District calendar to my phone?
Click the "Add to Calendar" button at the top of this page to download the iCal (.ics) file. Then:
iPhone/iPad: Tap the downloaded file, then tap "Add All" to add events to your Calendar app.
Android: Open the file with Google Calendar, review the events, and tap "Import".
Google Calendar (web): Go to Settings → Import & Export → Select the .ics file → Import.
Outlook: Double-click the file or drag it into your Outlook calendar.
Apple Calendar (Mac): Double-click the file or go to File → Import → select the .ics file.
What school district is Winsted, CT in?
Winsted, Connecticut is served by Winchester School District. This page shows the 2026-27 school calendar including first day, last day, breaks, and holidays.
When does school start in Winsted?
School in Winsted (Winchester School District) starts on Thursday, August 27, 2026 for the 2026-27 school year.
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Last updated: July 16, 2026