Official Chester Union Free School District 2026-2027 school calendar with holidays, breaks, PDF, and calendar sync. Chester Union Free School District School Calendar Includes all holidays, breaks, half days, and important dates from September 2026 through June 2027. Dates are manually collected and screened from district-published calendar materials. Printable PDF and Google/Apple Calendar sync options are available below. Updated 2026-10-04.
| Event | Date(s) | Status |
|---|---|---|
| First Day of School | September 2, 2026 (Wed) | School Opens |
| Labor Day | September 7, 2026 (Mon) | No School |
| Yom Kippur | September 21, 2026 (Mon) | No School |
| Columbus Day | October 12, 2026 (Mon) | No School |
| Student Holiday | November 3, 2026 (Tue) | No School |
| Veterans Day | November 11, 2026 (Wed) | No School |
| Thanksgiving Recess | November 25, 2026 - November 27, 2026 | No School |
| Winter Recess | December 24, 2026 - December 31, 2026 | No School |
| New Year's Day | January 1, 2027 (Fri) | No School |
| ML King Day | January 18, 2027 (Mon) | No School |
| Winter Recess | February 15, 2027 - February 19, 2027 | No School |
| Student Holiday | March 25, 2027 (Thu) | No School |
| Spring Recess | March 26, 2027 - April 2, 2027 | No School |
| Passover | April 22, 2027 (Thu) | No School |
| Memorial Day | May 31, 2027 (Mon) | No School |
| Juneteenth (observed) | June 18, 2027 (Fri) | No School |
| Last Day of School Students & Staff / ½ Day | June 25, 2027 (Fri) | School Closes |
Spot an error? Help us keep this calendar accurate.
| Period | Date(s) | Length |
|---|---|---|
| Thanksgiving Recess Window | Nov 25–29, 2026Districtwide no-school: Nov 25–27, 2026 · Adjacent weekend: Nov 28–29, 2026 | 5 days |
| Winter Recess Window | Dec 24, 2026–Jan 3, 2027Districtwide no-school: Dec 24, 2026–Jan 1, 2027 · Adjacent weekend: Jan 2–3, 2027 | 11 days |
| Winter Recess Window | Feb 13–21, 2027Districtwide no-school: Feb 15–19, 2027 · Adjacent weekend: Feb 13–14, 2027, Feb 20–21, 2027 | 9 days |
| Spring Recess Window | Mar 25–Apr 4, 2027Districtwide no-school: Mar 25–Apr 2, 2027 · Adjacent weekend: Apr 3–4, 2027 | 11 days |
View the full 2026-2027 school year by month.
Career exploration at Chester Union Free School District includes workplace experiences with local professionals. Chester Academy's internship program is open to juniors and seniors, with fields ranging from architecture and computer science to culinary work, education and healthcare. Students can investigate a possible direction before making decisions about study or employment after graduation.
The district's school sequence begins at Chester Elementary, serving prekindergarten through fifth grade, and continues at Chester Academy for grades six through twelve. Located in Orange County, it includes the Chester community and parts of Goshen and Blooming Grove. Students can explore public life through Youth-in-Government, which organizes mock political campaigns and elections, or through Mock Trial competitions judged by legal professionals. Middle school students also have a Kiwanis-affiliated Builders Club focused on service to school and community.
Data source & handling: Official calendar from Chester Union Free School District (chesterufsd.org). We manually collect and screen dates from district materials, then organize them into key dates, printable PDF, and calendar sync.
Disclaimer: This site is not affiliated with Chester Union Free School District or NYSED. Official calendars can change - always check chesterufsd.org before making plans.
Last updated: 2026-10-04