This is the official calendar of Windermere Preparatory School. Any questions, please contact Laine Allen (laine.allen@windermereprep.com).
| Upcoming Events | Date & Time |
| Middle School PE | Mon 12/15/2025 8:00 am - 3:00 pm |
| Middle School PE | Wed 12/17/2025 8:00 am - 2:00 pm |
| Early/Noon Dismissal - (LEAP Open) | Thu 12/18/2025 (All Day) |
| Teacher Work Day - NO SCHOOL (LEAP Open) | Fri 12/19/2025 (All Day) |
| Middle School PE | Fri 12/19/2025 8:00 am - 3:00 pm |
| Winter Break - No School | Sat 12/20/2025 (All Day) to Sun 01/04/2026 (All Day) |
| Middle School PE | Mon 12/22/2025 8:00 am - 3:00 pm |
| Middle School PE | Wed 12/24/2025 8:00 am - 2:00 pm |
| Middle School PE | Fri 12/26/2025 8:00 am - 3:00 pm |
| Middle School PE | Mon 12/29/2025 8:00 am - 3:00 pm |
| Middle School PE | Wed 12/31/2025 8:00 am - 2:00 pm |
| Middle School PE | Fri 01/02/2026 8:00 am - 3:00 pm |
| New Residential Life Students Arrive | Sat 01/03/2026 (All Day) |
| Residential Life Students Return | Sun 01/04/2026 (All Day) |
| Professional Development Day - NO SCHOOL (LEAP Open) | Mon 01/05/2026 (All Day) |
| Middle School PE | Mon 01/05/2026 8:00 am - 3:00 pm |
| Semester 2 Begins | Tue 01/06/2026 (All Day) |
| Middle School PE | Wed 01/07/2026 8:00 am - 2:00 pm |
| Middle School PE | Fri 01/09/2026 8:00 am - 3:00 pm |
| Middle School PE | Mon 01/12/2026 8:00 am - 3:00 pm |
| MS Q2 Celebration | Tue 01/13/2026 2:00 pm - 3:00 pm |
| Middle School PE | Wed 01/14/2026 8:00 am - 2:00 pm |
| Lifetouch Picture Retake Day | Thu 01/15/2026 7:30 am - 2:00 pm |
| Middle School PE | Fri 01/16/2026 8:00 am - 3:00 pm |
| Martin Luther King Jr. Holiday - NO SCHOOL | Mon 01/19/2026 (All Day) |
| MLK Jr Day - NO SCHOOL | Mon 01/19/2026 7:00 am - 3:00 pm |
| Middle School PE | Mon 01/19/2026 8:00 am - 3:00 pm |
| Learning Buddies | Tue 01/20/2026 2:30 pm - 3:30 pm |
| Middle School PE | Wed 01/21/2026 8:00 am - 2:00 pm |
| MS Book Club Meeting | Thu 01/22/2026 11:50 am - 12:20 pm |
| 7th Grade Sustainability Field Trip - Animal Kingdom | Fri 01/23/2026 7:30 am - 4:00 pm |
| Middle School PE | Fri 01/23/2026 8:00 am - 3:00 pm |
| Middle School PE | Mon 01/26/2026 8:00 am - 3:00 pm |
| Middle School PE | Wed 01/28/2026 8:00 am - 2:00 pm |
| Lower School Conference Day - NO SCHOOL LS | Fri 01/30/2026 (All Day) |
| Middle School PE | Fri 01/30/2026 8:00 am - 3:00 pm |
| Middle School PE | Mon 02/02/2026 8:00 am - 3:00 pm |
| MS Book Author Presentation | Tue 02/03/2026 8:00 am - 11:00 am |
| Middle School PE | Wed 02/04/2026 8:00 am - 2:00 pm |
| Middle School PE | Fri 02/06/2026 8:00 am - 3:00 pm |
| Admissions - Prospective Families Open House | Sat 02/07/2026 (8:00 am) 9:30 am - 11:30 am (1:00 pm) |
| Middle School PE | Mon 02/09/2026 8:00 am - 3:00 pm |
| Learning Buddies | Tue 02/10/2026 2:00 pm - 3:00 pm |
| Middle School PE | Wed 02/11/2026 8:00 am - 2:00 pm |
| Presidents' Day Weekend - NO SCHOOL | Fri 02/13/2026 (All Day) to Mon 02/16/2026 (All Day) |
| Middle School PE | Fri 02/13/2026 8:00 am - 3:00 pm |
| Middle School PE | Mon 02/16/2026 8:00 am - 3:00 pm |
| Middle School PE | Wed 02/18/2026 8:00 am - 2:00 pm |
| Middle School PE | Fri 02/20/2026 8:00 am - 3:00 pm |
| 7/8 SGA Valentine Formal | Sat 02/21/2026 7:00 pm - 10:00 pm |
| 7th Grade Eco-Adventure Field Trip - Crystal Springs | Mon 02/23/2026 8:00 am - 3:00 pm |
| Middle School PE | Mon 02/23/2026 8:00 am - 3:00 pm |
| 7th Grade Eco-Adventure Field Trip - Crystal Springs | Tue 02/24/2026 8:00 am - 3:00 pm |
| MS Career Day | Wed 02/25/2026 8:00 am - 2:00 pm |
| Middle School PE | Wed 02/25/2026 8:00 am - 2:00 pm |
| Middle School PE | Fri 02/27/2026 8:00 am - 3:00 pm |
| Middle School PE | Mon 03/02/2026 8:00 am - 3:00 pm |
| Learning Buddies | Tue 03/03/2026 12:00 pm - 1:00 pm |
| Middle School PE | Wed 03/04/2026 8:00 am - 2:00 pm |
| Middle School PE | Fri 03/06/2026 8:00 am - 3:00 pm |
| Middle School PE | Mon 03/09/2026 8:00 am - 3:00 pm |
| 8th Grade Cardboard Boat Regatta | Wed 03/11/2026 8:00 am - 2:00 pm |
| Middle School PE | Wed 03/11/2026 8:00 am - 2:00 pm |
| Early/Noon Dismissal - (LEAP Open) | Thu 03/12/2026 (All Day) |
| END OF Q3 - EARLY DISMISSAL DAY | Thu 03/12/2026 7:30 am - 12:00 pm |
| Professional Development Day - NO SCHOOL (LEAP Open) | Fri 03/13/2026 (All Day) |
| Middle School PE | Fri 03/13/2026 8:00 am - 3:00 pm |
| Start of Spring Break for Students - Professional Development Day | Fri 03/13/2026 8:00 am - 3:00 pm |
| Residential Life Dorms CLOSED | Mon 03/16/2026 (All Day) to Fri 03/20/2026 (All Day) |
| Spring Break - NO SCHOOL | Mon 03/16/2026 (All Day) to Fri 03/20/2026 (All Day) |
| SPRING BREAK - NO SCHOOL | Mon 03/16/2026 7:30 am - 3:00 pm |
| Middle School PE | Mon 03/16/2026 8:00 am - 3:00 pm |
| SPRING BREAK - NO SCHOOL | Tue 03/17/2026 7:30 am - 3:00 pm |
| SPRING BREAK - NO SCHOOL | Wed 03/18/2026 7:30 am - 3:00 pm |
| Middle School PE | Wed 03/18/2026 8:00 am - 2:00 pm |
| SPRING BREAK - NO SCHOOL | Thu 03/19/2026 7:30 am - 3:00 pm |
| SPRING BREAK - NO SCHOOL | Fri 03/20/2026 7:30 am - 3:00 pm |
| Middle School PE | Fri 03/20/2026 8:00 am - 3:00 pm |
| Middle School PE | Mon 03/23/2026 8:00 am - 3:00 pm |
| Middle School PE | Wed 03/25/2026 8:00 am - 2:00 pm |
| Middle School PE | Fri 03/27/2026 8:00 am - 3:00 pm |
| Middle School PE | Mon 03/30/2026 8:00 am - 3:00 pm |
| MS Q3 Celebration | Tue 03/31/2026 2:00 pm - 3:00 pm |
| Middle School PE | Wed 04/01/2026 8:00 am - 2:00 pm |
| Middle School PE | Fri 04/03/2026 8:00 am - 3:00 pm |
| 8th Grade Laker Adventures - "Go West" | Mon 04/06/2026 8:00 am to Fri 04/10/2026 9:00 pm |
| Middle School PE | Mon 04/06/2026 8:00 am - 3:00 pm |
| 7th Grade Laker Adventures - Discover Florida | Tue 04/07/2026 7:00 am to Fri 04/10/2026 7:00 pm |
| Middle School PE | Wed 04/08/2026 8:00 am - 2:00 pm |
| Book Fair Set Up | Thu 04/09/2026 11:00 am - 3:00 pm |
| Spring MS Book Fair | Fri 04/10/2026 7:00 am - 5:00 pm |
| Middle School PE | Fri 04/10/2026 8:00 am - 3:00 pm |
| NO SCHOOL (Hurricane Make Up Day) | Mon 04/13/2026 (All Day) |
| Spring MS Book Fair | Mon 04/13/2026 7:00 am - 5:00 pm |
| Middle School PE | Mon 04/13/2026 8:00 am - 3:00 pm |
| Spring MS Book Fair | Tue 04/14/2026 7:00 am - 5:00 pm |
| Learning Buddies | Tue 04/14/2026 2:30 pm - 3:30 pm |
| Spring MS Book Fair | Wed 04/15/2026 7:00 am - 5:00 pm |
| Middle School PE | Wed 04/15/2026 8:00 am - 2:00 pm |
| Spring MS Book Fair | Thu 04/16/2026 7:00 am - 5:00 pm |