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Weekend
Next 7 Days
October 2026
Coming Up
School Breaks
Holidays (No School)
The Cheshire School District school calendar for the 2026-27 school year runs from Tuesday, September 8, 2026 to Wednesday, June 16, 2027 in Cheshire Village, Connecticut.
- •4 scheduled breaks and 5 holidays throughout the year
- •Spring break: Apr 12 – Apr 16
- •Winter break: Dec 24 – Jan 1
Cheshire School District starts school 387 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 Cheshire School District dates with your phone or computer.
Frequently Asked Questions
Is Cheshire School District school open today?
No, today is Saturday - school is not in session on weekends.
When is the next day off for Cheshire School District?
The next day off is Thanksgiving Break, starting Thursday, November 26, 2026.
When is the first day of school for Cheshire School District?
The first day of school for Cheshire School District in 2026-27 is Tuesday, September 8, 2026.
When is the last day of school for Cheshire School District?
The last day of school for Cheshire School District in 2026-27 is Wednesday, June 16, 2027.
When is spring break for Cheshire School District?
Spring break for Cheshire School District is Monday, April 12, 2027 to Friday, April 16, 2027.
When is winter break for Cheshire School District?
Winter break for Cheshire School District is Thursday, December 24, 2026 to Friday, January 1, 2027.
When do students go back to school after winter break?
Students in Cheshire School District return to school after winter break on Monday, January 4, 2027. Winter break ends on Friday, January 1, 2027.
When is Thanksgiving break for Cheshire School District?
Thanksgiving break for Cheshire School District is Thursday, November 26, 2026 to Friday, November 27, 2026.
How do I add Cheshire 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 Cheshire Village, CT in?
Cheshire Village, Connecticut is served by Cheshire School District. This page shows the 2026-27 school calendar including first day, last day, breaks, and holidays.
When does school start in Cheshire Village?
School in Cheshire Village (Cheshire School District) starts on Tuesday, September 8, 2026 for the 2026-27 school year.
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Last updated: July 10, 2026