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June 2026
Coming Up
1 this weekSchool Breaks
Holidays (No School)
The Winchester School District school calendar for the 2025-26 school year runs from Wednesday, August 27, 2025 to Wednesday, June 10, 2026 in Winchester, Massachusetts.
- •5 scheduled breaks and 7 holidays throughout the year
- •Spring break: Apr 13 – Apr 17
- •Winter break: Dec 24 – Dec 31
Winchester School District starts school 8 days later than most Massachusetts districts. Winter break starts 54 days earlier than the most common Massachusetts 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?
No, today is Saturday - school is not in session on weekends.
When is the next day off for Winchester School District?
There are no more scheduled days off for the 2025-26 school year.
When is the first day of school for Winchester School District?
The first day of school for Winchester School District in 2025-26 is Wednesday, August 27, 2025.
When is the last day of school for Winchester School District?
The last day of school for Winchester School District in 2025-26 is Wednesday, June 10, 2026.
When is spring break for Winchester School District?
Spring break for Winchester School District is Monday, April 13, 2026 to Friday, April 17, 2026.
When is winter break for Winchester School District?
Winter break for Winchester School District is Wednesday, December 24, 2025 to Wednesday, December 31, 2025.
When do students go back to school after winter break?
Students in Winchester School District return to school after winter break on Thursday, January 1, 2026. Winter break ends on Wednesday, December 31, 2025.
When is Thanksgiving break for Winchester School District?
Thanksgiving break for Winchester School District is Wednesday, November 26, 2025 to Friday, November 28, 2025.
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 Winchester, MA in?
Winchester, Massachusetts is served by Winchester School District. This page shows the 2025-26 school calendar including first day, last day, breaks, and holidays.
When does school start in Winchester?
School in Winchester (Winchester School District) starts on Wednesday, August 27, 2025 for the 2025-26 school year.
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Last updated: January 2, 2026