Caroline County Public Schools Calendar 2026-2027
Complete holiday schedule and key dates for Caroline County Public Schools for the 2026-2027 academic year.
Key Dates
| Event | Date(s) | Status |
|---|---|---|
| First Day of School | August 26, 2026 (Wed) | School Opens |
| Labor Day | September 7, 2026 (Mon) | No School |
| MSEA Convention | October 16, 2026 (Fri) | No School |
| Student Holiday | November 3, 2026 (Tue) | No School |
| Student Holiday | November 13, 2026 (Fri) | No School |
| Thanksgiving Break | November 25, 2026 - November 27, 2026 | No School |
| Winter Break | December 18, 2026 - January 1, 2027 | No School |
| Martin Luther King Jr. Day | January 18, 2027 (Mon) | No School |
| Student Holiday | January 25, 2027 (Mon) | No School |
| Student Holiday | February 12, 2027 (Fri) | No School |
| Presidents' Day | February 15, 2027 (Mon) | No School |
| Student Holiday | March 8, 2027 (Mon) | No School |
| Spring Break | March 24, 2027 - March 29, 2027 | No School |
| Student Holiday | May 28, 2027 (Fri) | No School |
| Memorial Day | May 31, 2027 (Mon) | No School |
| Last Day of School | June 11, 2027 (Fri) | School Closes |
Monthly Calendar MarylandSchoolCalendar.com
View the full 2026-2027 school year by month.
Calendar Notes
Caroline County starts K-12 students on August 26, 2026, later than Dorchester, Queen Anne's, and Talbot but earlier than Cecil, Kent, Wicomico, Somerset, and Worcester. Pre-K orientation, the first day for Pre-K students, graduation dates, and teacher-only items are not listed as public dated events here when the source marks them TBD. That keeps the page focused on confirmed family-facing dates rather than placeholders.
The half-day pattern is a major planning feature. Caroline lists half days on October 30, December 18, January 22, February 12, March 24, April 2, May 28, and June 11. Several are tied to quarter endings, professional development, or conferences, so they are not interchangeable with a full closure. For families arranging after-school care, those half days may matter more than the named holidays.
Caroline builds three days into the calendar for inclement weather, and the June 11 last day is marked subject to change. Its winter break runs December 21-January 1, matching several Eastern Shore systems, while spring break runs March 25-29. That spring window starts one day earlier than Wicomico, Worcester, Kent, and Talbot, and does not extend as long as Queen Anne's March 26-April 2 break.
- First day for K-12 students: August 26, 2026
- Last day for students: June 11, 2027, subject to change
- Three days are built into the calendar for inclement weather
Frequently Asked Questions
The first day for Caroline County Public Schools K-12 students is Wednesday, August 26, 2026. The Pre-K first day is listed as TBD on the official calendar.
The official calendar lists Friday, June 11, 2027, as a half-day last day for students, subject to change.
Yes. Half days are included because they affect dismissal time and family planning.
The first day of school for Caroline County Public Schools students is Wednesday, August 26, 2026. Teachers typically report a few days earlier for staff development. Parents should check the district website for any orientation sessions, supply list deadlines, or staggered-start schedules that may apply to younger grades.
Caroline County Public Schools Winter Break runs from December 21, 2026 through January 1, 2027 — that's 10 school days off. Including the adjacent weekends, families have up to 16 consecutive days for holiday travel and family time. Students return to class on Monday, January 4, 2027.
Caroline County Public Schools Thanksgiving Break is November 25, 2026 through November 27, 2026, giving students 3 weekdays off. With the surrounding weekends, families get 5 consecutive days away from school — enough time for out-of-state travel or extended family gatherings.
Caroline County Public Schools Spring Break is March 25, 2027 through March 29, 2027 - 3 school days off. Including the weekends on either side, families have up to 5 consecutive days for vacation planning. Note that neighboring school systems may have different Spring Break weeks, so coordinate if you have children in multiple systems.
Yes. Caroline County Public Schools has designated potential bad-weather make-up days. If no weather closures occur, these days typically remain regular holidays for students. Missed days are handled under Maryland school calendar requirements and local school system guidance.
Caroline County Public Schools schedules 8 teacher-only or professional development days during 2026-2027 when students do not attend. These include: November 3, 2026 (Professional Development Day); November 13, 2026 (Professional Development and Parent Conferences); January 25, 2027 (Transition/Planning Day); March 8, 2027 (Professional Development Day). On these days, teachers participate in training and curriculum planning while students have the day off. Parents should arrange childcare if needed, as after-school programs may also be closed.
Between the first day (August 26, 2026) and last day (June 11, 2027), Caroline County Public Schools students have approximately 25 weekdays off for holidays, breaks, and teacher workdays. That leaves roughly 183 potential instructional days across the school year. Maryland school systems generally plan around state instructional-day requirements and local board-approved calendars.
Related Links
About This Calendar
Data Source: Official Caroline County Public Schools 2026-2027 District Calendar PDF.
Disclaimer: This website is not affiliated with Caroline County Public Schools, the Maryland State Department of Education, or any official school system body. While we strive for accuracy, always verify important dates with the official school system website.