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Weekend
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 Wednesday, September 2, 2026 to Thursday, June 17, 2027 in Winchester, Massachusetts.
- •3 scheduled breaks and 7 holidays throughout the year
- •Spring break: Apr 19 – Apr 23
- •Winter break: Dec 24 – Jan 1
Winchester School District starts school 379 days later than most Massachusetts districts. Winter break starts 311 days later 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?
The next day off is Monday, October 12, 2026 for No School (Indigenous Peoples' Day).
When is the first day of school for Winchester School District?
The first day of school for Winchester School District in 2026-27 is Wednesday, September 2, 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 Thursday, June 17, 2027.
When is spring break for Winchester School District?
Spring break for Winchester School District is Monday, April 19, 2027 to Friday, April 23, 2027.
When is winter break for Winchester School District?
Winter break for Winchester School District is Thursday, December 24, 2026 to Friday, January 1, 2027.
When do students go back to school after winter break?
Students in Winchester 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 Winchester School District?
Thanksgiving break dates for Winchester School District are not yet available.
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 2026-27 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, September 2, 2026 for the 2026-27 school year.
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Last updated: July 15, 2026