September 2019
| Wednesday 11 | Opening Day (parents only) |
| Thursday 12 | Visiting Day (brief 15-minute visit with children and one adult) |
| Friday 13 | Returning Children Begin |
| Monday 16 | Phase-in for new children begins |
| Tuesday 24 | PA Meeting & Speaker Series “Montessori at Home” |
October
| Tuesday/Wednesday 2/3 | Class Dinners |
| Monday 14 | WSMS Closed, Columbus Day |
| Saturday 19 | Fall Festival |
November
| Saturday 2 | Bulb Planting at Hippo Park |
| Monday 11 | WSMS Closed, Conference Day |
| Wednesday-Friday 27-29 | WSMS Closed, Thanksgiving Break |
December
| Monday-Wednesday 2-4 | Winter Clothing Drive / Winter Pop-Up Shop |
| Friday 13 | WSMS Closed, Professional Development Day |
| Friday 20 | Early dismissal for LAP at 12:30 p.m. No PM classes. |
| Monday-Friday (2 Weeks) 23-3 | Winter Break, Vacation School in session 5 days for registered students (12/26, 12/27, 12/30, 1/2, 1/3) |
January 2020
| Monday 6 | School Resumes |
| Monday 20 | WSMS Closed, Martin Luther King Jr. Day |
| Thursday 30 | Auction Class Art Project Reveal Parties |
| Friday 31 | WSMS Auction, 7:30 p.m. |
February
| Monday-Tuesday 17-18 | WSMS Closed, Presidents’ Day Break |
March
| Friday 13 | Early dismissal for LAP at 12:30 p.m. No PM classes. |
| Monday-Friday (2 Weeks) 16-27 | Spring Break, Vacation School in session 10 days for registered students |
| Monday 30 | School Resumes |
April
| Friday 17 | WSMS Closed, Professional Development Day |
May
| Friday 1 | WSMS Closed, Conference Day |
| Saturday 2 | Hooked on Books! Children’s Book Festival |
| Monday 25 | WSMS Closed, Memorial Day |
| Thursday 28 | PA Appreciation Party |
June
| Wednesday 3 | Year-End School Picnic |
| Wednesday 10 | Last Day For Academic Year Children (early dismissal after ceremony) |
| Thursday-Friday 11-12 | WSMS Closed, Camp Set-Up Days |
| Monday 15 | Summer Camp Begins |
July
| Friday 3 | WSMS Closed, Independence Day Observed |
August
| Friday 7 | Summer Camp Ends |
