| Thu | August 2 | Registration, 1:00-6:00 PM - Office |
| Fri | August 3 | Registration, 7:00 AM - 1:00 PM - Office |
| Mon | August 27 | SASD Presession |
| Mon | August 27 | Open House, 5:00-6:00 PM |
| Tue | August 28 | SASD Presession |
| Wed | August 29 | SASD Professional Development Day |
| Mon | September 3 | SASD No School - Labor Day |
| Tue | September 4 | SASD First Day of School |
| Fri | September 7 | 4-year-old Kindergarten First Day of School, 8:40-11:45 AM |
| Mon | September 10 | PTO Meeting, 6:00-7:00 PM - Library |
| Tue | October 2 | 5th Grade Outdoor Skills, 8:45 AM - 2:10 PM - Sheboygan Marsh |
| Tue | October 2 | SASD Human Growth & Development Parent Preview Night held at Longfellow Elementary, 6:30-8:00 PM |
| Wed | October 3 | PTO Walk-A-Thon Fundraiser |
| Wed | October 3 | Walk to School Day, 8:00-8:45 AM |
| Thu | October 4 | 5th Grade Outdoor Skills, 8:45 AM - 2:10 PM - Sheboygan Marsh |
| Mon | October 8 | PTO Meeting, 6:00-7:00 PM - Library |
| Fri | October 12 | Picture Day, 8:30 AM - 12:30 PM |
| Fri | October 12 | SASD North/South Football Game, 7:00-9:00 PM - North High |
| Fri | October 19 | Halloween Pot Luck, 5:30-7:00 PM |
| Thu-Fri | October 25-26 | SASD No School - Fall Recess |
| Fri | November 9 | SASD First Quarter Ends |
| Mon | November 12 | SASD Second Quarter Begins |
| Mon | November 12 | PTO Meeting, 6:00-7:00 PM - Library |
| Thu | November 15 | Early Release - 12:00 PM |
| Thu | November 15 | Parent-Teacher Conferences, 1:00-7:00 PM |
| Tue | November 20 | Parent-Teacher Conference, 4:00-7:00 PM |
| Thu-Fri | November 22-23 | SASD No School - Thanksgiving Recess |
| Fri | December 7 | Holiday Shop, 5:00-6:30 PM |
| Mon | December 10 | PTO Meeting, 6:00-7:00 PM - Library |
| Thu | December 20 | Winter Sing, 2:00-3:30 PM |
| Fri | December 21 | SASD 2-Hour Early Release, 1:30 PM |
| Mon-Tue | December 24-January 1 | SASD No School - Winter Recess |
| Mon-Tue | December 24-January 1 | SASD No School - Winter Recess |
| Wed | January 2 | SASD Classes Resume |
| Mon | January 14 | PTO Meeting, 6:00-7:00 PM - Library |
| Fri | January 18 | Family Fun Night, 6:00-8:00 PM - Gym |
| Thu | January 24 | SASD Second Quarter Ends |
| Fri | January 25 | SASD Teacher Records Day - No School for Students |
| Mon | January 28 | SASD Third Quarter Begins |
| Thu | January 31 | Early Release - 12:00 PM |
| Thu | January 31 | Parent-Teacher Conferences, 1:00-7:00 PM |
| Tue | February 5 | Parent-Teacher Conferences, 4:00-7:00 PM |
| Wed | February 6 | SASD Digital Learning Day Open House - District-wide |
| Mon | February 11 | PTO Meeting, 6:00-7:00 PM - Library |
| Fri | February 15 | Dance, 6:00-8:00 PM |
| Mon | February 18 | SASD No School - President's Day Recess |
| Thu | March 7 | Cleveland/Montessori Present..., 6:00-7:00 PM |
| Mon | March 11 | PTO Meeting, 6:00-7:00 PM - Library |
| Sat | March 16 | CANCELLED-Spring Egg Hunt, 10:00 AM - 12:00 PM |
| Fri | March 22 | SASD 2-Hour Early Release, 1:30 PM |
| Mon-Mon | March 25-April 1 | SASD No School - Spring Break |
| Mon-Mon | March 25-April 1 | SASD No School - Spring Break |
| Tue | April 2 | SASD School Resumes |
| Fri | April 5 | SASD Third Quarter Ends |
| Mon | April 8 | SASD Fourth Quarter Begins |
| Mon | April 8 | PTO Meeting, 6:00-7:00 PM - Library |
| Thu | April 11 | SASD All District String Festival, 7:00-9:00 PM - North High School Fieldhouse |
| Thu | May 2 | SASD 5th Grade Presidential Awards, 6:00-7:30 PM - South High School Auditorium |
| Mon | May 13 | PTO Meeting, 6:00-7:00 PM - Library |
| Fri | May 17 | SASD Emergency Make-Up Day - Due to Second Snow Day |
| Tue | May 21 | 4K Orientation, 6:00-7:00 PM |
| Thu | May 23 | SASD 5th Grade Sports Day CANCELLED, 9:00 AM - 2:00 PM - South High School |
| Fri | May 24 | SASD Emergency Make-Up Day - NO SCHOOL |
| Mon | May 27 | SASD No School - Memorial Day |
| Tue | May 28 | SASD 5th Grade Sports Day RESCHEDULED, 8:45 AM - 2:45 PM - South High |
| Wed | June 12 | SASD Fourth Quarter Ends - Last Day of School |
| Thu | June 13 | SASD Teacher Reports Day - No School for Students |