Complete school year calendar for the Middletown Enlarged City School District in Orange County — one of the few Mid-Hudson districts to observe Eid al-Fitr as an official school holiday starting in 2026-2027. Includes all holidays, breaks, half days, and important dates from September 2025 through June 2026.
| Event | Date(s) | Status |
|---|---|---|
| First Day of School | September 3, 2025 (Wed) | School Opens |
| Labor Day | September 1, 2025 (Mon) | No School |
| Superintendent's Conference Day | September 2, 2025 (Tue) | No School |
| Rosh Hashanah | September 22–23, 2025 (Mon–Tue) | No School |
| Yom Kippur | October 2, 2025 (Thu) | No School |
| Columbus Day / Indigenous Peoples' Day | October 13, 2025 (Mon) | No School |
| Superintendent's Conference Day | November 4, 2025 (Tue) | No School |
| Veterans Day | November 11, 2025 (Tue) | No School |
| Half Day (Pre-Thanksgiving) | November 26, 2025 (Wed) | Half Day |
| Thanksgiving Recess | November 27–28, 2025 (Thu–Fri) | No School |
| Winter Recess | Dec 24, 2025 – Jan 2, 2026 | No School |
| Martin Luther King Jr. Day | January 19, 2026 (Mon) | No School |
| Regents Exams (January) | January 20–23, 2026 | Regents |
| Mid-Winter Recess | February 16–18, 2026 (Mon–Wed) | No School |
| Superintendent's Conference Day | March 6, 2026 (Fri) | No School |
| Spring Recess | March 30 – April 3, 2026 (Mon–Fri) | No School |
| Superintendent's Conference Day | May 15, 2026 (Fri) | No School |
| Memorial Day | May 25, 2026 (Mon) | No School |
| Regents Exams (June) | June 17–26, 2026 | Regents |
| Juneteenth | June 19, 2026 (Fri) | No School |
| Last Day of School | June 25, 2026 (Thu) | School Closes |
Complete month-by-month calendar from September 2025 to June 2026. Every day is color-coded so you can see school days, holidays, and breaks at a glance.
The Middletown City School District (also called the Enlarged City School District of Middletown, or ECSDM) 2025-2026 school year runs from September 3, 2025 to June 25, 2026. The district serves approximately 7,000 students across 10 schools in Orange County, making it one of the larger districts in the Mid-Hudson region. Middletown sits about 65 miles northwest of New York City, giving families a suburban feel while still being within commuting distance of the metro area.
One of the key calendar features for 2025-2026 is the relatively short mid-winter recess — only three days (February 16–18), compared to the full week that many Long Island and Westchester districts take. This is because ECSDM builds its calendar to reach approximately 181 student-attendance days, and a shorter February break allows the school year to end by late June without pushing into summer. Families who also have children in nearby Newburgh should note that break schedules may not perfectly align.
Middletown's spring recess runs from March 30 to April 3, 2026 — a full week. This is about a week earlier than some neighboring districts that align their break with Easter week. The district also observes both Rosh Hashanah (two days) and Yom Kippur, giving families three additional days off in September and October that not all upstate districts provide.
The district schedules four Superintendent's Conference Days throughout the year (September 2, November 4, March 6, and May 15) — these are days when students have no school but teachers attend professional development. Parents should mark these on their calendars as they are easy to miss. There is also a half day on November 26 (the day before Thanksgiving), which is common across most New York districts.
Regents Exams are held January 20–23, 2026 (midyear) and June 17–26 (end-of-year). During June Regents week, high school students on modified schedules may have different dismissal times. The district typically builds in 3-5 snow days as buffer before the last day of school; if unused, they may shift the final day earlier.
For easy reference, use the button at the top of this page to download a free, color-coded printable Middletown school calendar for your fridge or classroom.
The first day of school is Wednesday, September 3, 2025. September 1 is Labor Day and September 2 is a Superintendent's Conference Day.
Winter Recess runs from December 24, 2025 through January 2, 2026. Students return on Monday, January 5.
Spring Recess runs from March 30 – April 3, 2026, a full week off.
The last day of school is Thursday, June 25, 2026.
November 26 is a half day (shortened session). Schools are fully closed November 27–28 for Thanksgiving.
Middletown schedules a shorter mid-winter recess (February 16–18) compared to the full week many other districts take. This keeps the total school year within roughly 181 student-attendance days and allows the year to end in late June without extending into summer.
Yes. Schools are closed September 22–23 for Rosh Hashanah and October 2 for Yom Kippur. Not all Mid-Hudson districts observe both days of Rosh Hashanah, making this a notable calendar feature.
There are 4 conference days in 2025-2026: September 2, November 4, March 6, and May 15. Students have no school on these days even though they are weekdays.
Data Source: This calendar is based on the official 2025-2026 calendar published by the Middletown City School District (Revised 4-24-25).
Disclaimer: This website is not affiliated with, endorsed by, or connected to Middletown City School District or the New York State Education Department (NYSED). For the most current and official calendar, please visit www.middletowncityschools.org.
Dates are subject to change. Religious holiday dates are approximate and based on projected lunar calendar calculations.
Last updated: March 29, 2026