⚠Unofficial calendar. Always confirm with your district before making plans. Some dates are estimated from nearby districts or past years — those are marked below.
Winchester
Massachusetts · 4,331 students · 2026–27 school year
Showing the 2026–27 school year. Past years & forecasts are in our API.
Winter
Nov 25 – Nov 25
Spring
Mar 31 – Apr 2
Last day
May 28
Breaks & no-school days
Day off
Starts
Ends
Teacher Work Day
—
Teacher Professional Development Day
—
Teacher Work Day
—
Teacher Work Day
—
Teacher Work Day
—
Teacher Work Day
—
Teacher Professional Development Day
—
Division Holiday
—
End Of 1St Quarter
—
Teacher Work From Home Day
—
Teacher Professional Development Day
—
Winter Break
—
Fall Break; Division Holiday
—
Winter Break
—
Teacher Work From Home Day
—
Holiday For Students And Teachers
—
Division Holiday
—
Division Holiday
—
Division Holiday
—
Holiday For Students And Teachers
—
Holiday For Students And Teachers
—
Holiday For Students And Teachers
—
Holiday For Students And Teachers
—
Division Holiday
—
Teacher Professional Development Day
—
Division Holiday
—
Teacher Professional Development Day
—
Division Holiday
—
End Of 3Rd Quarter
—
Teacher Work From Home Day
—
Division Holiday
—
Spring Break
Division Holiday
—
Division Holiday
—
Teacher Work Day
—
Teacher Work From Home Day
—
School dayDay offHalf dayEstimated — not yet confirmed by the district