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School Open
Dismissal: 3:30 PM
Next 7 Days
April 2026
Coming Up
School Breaks
Holidays (No School)
The Cheshire School District school calendar for the 2025-26 school year runs from Thursday, August 21, 2025 to Thursday, June 4, 2026 in Cheshire Village, Connecticut.
- •4 scheduled breaks and 7 holidays throughout the year
- •Spring break: Apr 6 – Apr 10
- •Winter break: Dec 24 – Jan 2
Cheshire School District starts school 4 days later than most Connecticut districts. Winter break matches the most common Connecticut schedule, starting 12/24.
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?
Yes, Cheshire School District is open today. Check the weekly calendar above for upcoming school days and closures.
When is the next day off for Cheshire School District?
The next day off is Monday, May 25, 2026 for Memorial Day.
When is the first day of school for Cheshire School District?
The first day of school for Cheshire School District in 2025-26 is Thursday, August 21, 2025.
When is the last day of school for Cheshire School District?
The last day of school for Cheshire School District in 2025-26 is Thursday, June 4, 2026.
When is spring break for Cheshire School District?
Spring break for Cheshire School District is Monday, April 6, 2026 to Friday, April 10, 2026.
When is winter break for Cheshire School District?
Winter break for Cheshire School District is Wednesday, December 24, 2025 to Friday, January 2, 2026.
When do students go back to school after winter break?
Students in Cheshire School District return to school after winter break on Monday, January 5, 2026. Winter break ends on Friday, January 2, 2026.
When is Thanksgiving break for Cheshire School District?
Thanksgiving break for Cheshire School District is Thursday, November 27, 2025 to Friday, November 28, 2025.
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 2025-26 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 Thursday, August 21, 2025 for the 2025-26 school year.
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Last updated: January 3, 2026