 23 |
7th Grade Sustainability Field Trip - Animal Kingdom |  7th Grade |
 Active |
| Friday, January 23, 2026 7:30 am - 4:00 pm | |||
 Disney's Animal Kingdom Theme Park |
| 23 |
Middle School PE | PE |
Active |
| Friday, January 23, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 23 |
Nord Anglia Performing Arts Festival |  Fine Arts |
Active |
| Friday, January 23, 2026 12:00 pm - 9:00 pm | |||
| Windermere Preparatory School › Cypress Center for the ArtsWindermere Preparatory School › Middle School › Laker LoungeWindermere Preparatory School › Middle School › MS Classrooms › 7th Grade Classrooms |
| 26 |
Middle School PE | Active |
|
| Monday, January 26, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 28 |
Middle School PE | Active |
|
| Wednesday, January 28, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 30 |
Middle School PE | Active |
|
| Friday, January 30, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 2 |
Middle School PE | Active |
|
| Monday, February 2, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 2 |
Set up for Author Visit | Middle School |
Active |
| Monday, February 2, 2026 3:00 pm - 4:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 3 |
MS Book Author Presentation | Middle School |
Active |
| Tuesday, February 3, 2026 8:00 am - 9:30 am | |||
| Windermere Preparatory School › Learning Commons |
| 3 |
MS Cheer End of Season Party | Active |
|
| Tuesday, February 3, 2026 3:00 pm - 4:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 4 |
Middle School PE | Active |
|
| Wednesday, February 4, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 6 |
Middle School PE | Active |
|
| Friday, February 6, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 7 |
Admissions - Prospective Families Open House | AthleticsHigh SchoolLower SchoolMiddle SchoolFine Arts |
Active |
| Saturday, February 7, 2026 (8:00 am) 9:30 am - 11:30 am (1:00 pm) | |||
| Windermere Preparatory School › Middle School › Laker LoungeWindermere Preparatory School › Learning CommonsWindermere Preparatory School › Cypress Center for the Arts |
| 9 |
Middle School PE | Active |
|
| Monday, February 9, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 9 |
Rising 9's Event | Active |
|
| Monday, February 9, 2026 6:00 pm - 7:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 10 |
Learning Buddies | Active |
|
| Tuesday, February 10, 2026 2:00 pm - 3:00 pm | |||
| Windermere Preparatory School › Middle School |
| 11 |
Middle School PE | Active |
|
| Wednesday, February 11, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 13 |
Middle School PE | Active |
|
| Friday, February 13, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 16 |
Middle School PE | Active |
|
| Monday, February 16, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 17 |
MYP Design Criterion C Rollout | Active |
|
| Tuesday, February 17, 2026 2:00 pm - 3:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 18 |
Middle School PE | Active |
|
| Wednesday, February 18, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 19 |
MS Book Club | Middle School |
Active |
| Thursday, February 19, 2026 11:50 am - 12:20 pm | |||
| Windermere Preparatory School › Learning Commons |
| 20 |
Middle School PE | Active |
|
| Friday, February 20, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 21 |
7/8 SGA Valentine Formal | Active |
|
| Saturday, February 21, 2026 7:00 pm - 10:00 pm | |||
| Hyatt Grand Cypress Hotel |
| 23 |
Middle School PE | Active |
|
| Monday, February 23, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 23 |
7th Grade Eco-Adventure Field Trip - Crystal Springs | Active |
|
| Monday, February 23, 2026 8:00 am - 3:00 pm | |||
| Crystal Springs |
| 24 |
7th Grade Eco-Adventure Field Trip - Crystal Springs | Middle School |
Active |
| Tuesday, February 24, 2026 8:00 am - 3:00 pm | |||
| Crystal Springs |
| 25 |
Middle School PE | Active |
|
| Wednesday, February 25, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 25 |
MS Career Day | Middle School |
Active |
| Wednesday, February 25, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School |
| 26 |
MS Book Club | Middle School |
Active |
| Thursday, February 26, 2026 11:50 am - 12:20 pm | |||
| Windermere Preparatory School › Learning Commons |
| 27 |
Middle School PE | Active |
|
| Friday, February 27, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 1 |
MS Theatre | Middle School |
Active |
| Sunday, March 1, 2026 3:30 pm - 6:00 pm | |||
| Windermere Preparatory School › Cypress Center for the Arts › Black Box › MS Black Box (CC127) |
| 2 |
Middle School PE | Active |
|
| Monday, March 2, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 3 |
Learning Buddies | Middle School |
Active |
| Tuesday, March 3, 2026 12:00 pm - 1:00 pm | |||
| Windermere Preparatory School › Middle School |
| 4 |
Middle School PE | Active |
|
| Wednesday, March 4, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 6 |
Middle School PE | Active |
|
| Friday, March 6, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 9 |
Rising 9th graders -Charting the path ahead | Active |
|
| Monday, March 9, 2026 8:00 am - 9:00 am | |||
| Windermere Preparatory School › Learning Commons |
| 9 |
Middle School PE | Active |
|
| Monday, March 9, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 9 |
Rising 9th graders -Charting the path ahead | Active |
|
| Monday, March 9, 2026 6:00 pm - 7:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 11 |
Middle School PE | Active |
|
| Wednesday, March 11, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 11 |
8th Grade Cardboard Boat Regatta | Active |
|
| Wednesday, March 11, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle SchoolWindermere Preparatory School › Athletics › Pool |
| 12 |
END OF Q3 - EARLY DISMISSAL DAY | Active |
|
| Thursday, March 12, 2026 7:30 am - 12:00 pm | |||
| Windermere Preparatory School › Lower SchoolWindermere Preparatory School › Middle SchoolWindermere Preparatory School › High School |
| 13 |
Middle School PE | Active |
|
| Friday, March 13, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 13 |
Start of Spring Break for Students - Professional Development Day | Active |
|
| Friday, March 13, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle SchoolWindermere Preparatory School › Lower SchoolWindermere Preparatory School › High School |
| 16 |
SPRING BREAK - NO SCHOOL | Active |
|
| Monday, March 16, 2026 7:30 am - 3:00 pm | |||
| Windermere Preparatory School › Lower SchoolWindermere Preparatory School › Middle SchoolWindermere Preparatory School › High School |
| 16 |
Middle School PE | Active |
|
| Monday, March 16, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 17 |
SPRING BREAK - NO SCHOOL | Active |
|
| Tuesday, March 17, 2026 7:30 am - 3:00 pm | |||
| Windermere Preparatory School › High SchoolWindermere Preparatory School › Middle SchoolWindermere Preparatory School › Lower School |
| 18 |
SPRING BREAK - NO SCHOOL | Active |
|
| Wednesday, March 18, 2026 7:30 am - 3:00 pm | |||
| Windermere Preparatory School › High SchoolWindermere Preparatory School › Middle SchoolWindermere Preparatory School › Lower School |
| 18 |
Middle School PE | Active |
|
| Wednesday, March 18, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 19 |
SPRING BREAK - NO SCHOOL | Active |
|
| Thursday, March 19, 2026 7:30 am - 3:00 pm | |||
| Windermere Preparatory School › High SchoolWindermere Preparatory School › Middle SchoolWindermere Preparatory School › Lower School |
| 20 |
SPRING BREAK - NO SCHOOL | Active |
|
| Friday, March 20, 2026 7:30 am - 3:00 pm | |||
| Windermere Preparatory School › High SchoolWindermere Preparatory School › Middle SchoolWindermere Preparatory School › Lower School |
| 20 |
Middle School PE | Active |
|
| Friday, March 20, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 23 |
Middle School PE | Active |
|
| Monday, March 23, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 25 |
Middle School PE | Active |
|
| Wednesday, March 25, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 27 |
Middle School PE | Active |
|
| Friday, March 27, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 30 |
Middle School PE | Active |
|
| Monday, March 30, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 31 |
MS Q3 Celebration | Active |
|
| Tuesday, March 31, 2026 2:00 pm - 3:00 pm | |||
| Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre |
| 1 |
Middle School PE | Active |
|
| Wednesday, April 1, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 3 |
Middle School PE | Active |
|
| Friday, April 3, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 6 |
Middle School PE | Active |
|
| Monday, April 6, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 6 |
8th Grade Laker Adventures - "Go West" | Active |
|
| Monday, April 6, 2026 8:00 am to Friday, April 10, 2026 9:00 pm |
|||
| Grand Canyon |
| 7 |
7th Grade Laker Adventures - Discover Florida | Active |
|
| Tuesday, April 7, 2026 7:00 am to Friday, April 10, 2026 7:00 pm |
|||
| Florida Keys |
| 8 |
Middle School PE | Active |
|
| Wednesday, April 8, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 9 |
Book Fair Set Up | Middle School |
Active |
| Thursday, April 9, 2026 11:00 am - 3:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 10 |
Spring MS Book Fair | Middle School |
Active |
| Friday, April 10, 2026 7:00 am - 5:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 10 |
Middle School PE | Active |
|
| Friday, April 10, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 13 |
Spring MS Book Fair | Middle School |
Active |
| Monday, April 13, 2026 7:00 am - 5:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 13 |
Middle School PE | Active |
|
| Monday, April 13, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 14 |
Spring MS Book Fair | Middle School |
Active |
| Tuesday, April 14, 2026 7:00 am - 5:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 14 |
Learning Buddies | Active |
|
| Tuesday, April 14, 2026 2:30 pm - 3:30 pm | |||
| Windermere Preparatory School › Middle School |
| 15 |
Spring MS Book Fair | Middle School |
Active |
| Wednesday, April 15, 2026 7:00 am - 5:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 15 |
Middle School PE | Active |
|
| Wednesday, April 15, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 16 |
Spring MS Book Fair | Middle School |
Active |
| Thursday, April 16, 2026 7:00 am - 5:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 16 |
 MS Art Showcase Setup |
Fine Arts |
 Cancelled |
| Thursday, April 16, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › MS Porches |
| 17 |
Spring MS Book Fair | Middle School |
Active |
| Friday, April 17, 2026 7:00 am - 5:00 pm | |||
| Windermere Preparatory School › Learning Commons |
| 17 |
MS Art Showcase |
Fine Arts |
Cancelled |
| Friday, April 17, 2026 7:00 am - 5:30 pm | |||
| Windermere Preparatory School › Middle School › MS PorchesWindermere Preparatory School › Cypress Center for the Arts › Atrium (CC100) |
| 17 |
LS/MS ONLY Conference Day - HS IN SESSION | Middle SchoolLower School |
Active |
| Friday, April 17, 2026 7:30 am - 3:00 pm | |||
| Windermere Preparatory School › Middle SchoolWindermere Preparatory School › Lower School |
| 17 |
Middle School PE | Active |
|
| Friday, April 17, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 20 |
Middle School PE | Active |
|
| Monday, April 20, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 22 |
Middle School PE | Active |
|
| Wednesday, April 22, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 22 |
7th Grade Earth Day Outing | Active |
|
| Wednesday, April 22, 2026 10:00 am - 2:00 pm | |||
| Beck Brothers Citrus Inc |
| 24 |
Middle School PE | Active |
|
| Friday, April 24, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 27 |
Middle School PE | Active |
|
| Monday, April 27, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 29 |
Middle School PE | Active |
|
| Wednesday, April 29, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 1 |
Middle School PE | Active |
|
| Friday, May 1, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 4 |
Middle School PE | Active |
|
| Monday, May 4, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 5 |
Learning Buddies | Active |
|
| Tuesday, May 5, 2026 2:00 pm - 3:00 pm | |||
| Windermere Preparatory School › Middle School |
| 5 |
7th Grade Seedfolks Garden Party | Active |
|
| Tuesday, May 5, 2026 6:00 pm - 9:00 pm | |||
| Windermere Preparatory School › Middle School |
| 6 |
Middle School PE | Active |
|
| Wednesday, May 6, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 8 |
Middle School PE | Active |
|
| Friday, May 8, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 11 |
Middle School PE | Active |
|
| Monday, May 11, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 12 |
8th Grade TAP Rehearsal | Active |
|
| Tuesday, May 12, 2026 1:00 pm - 2:00 pm | |||
| Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre |
| 12 |
MS Q4 Celebration | Middle School |
Active |
| Tuesday, May 12, 2026 2:00 pm - 3:00 pm | |||
| Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre |
| 13 |
Middle School PE | Active |
|
| Wednesday, May 13, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 15 |
Middle School PE | Active |
|
| Friday, May 15, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 15 |
TAP Practice | Fine Arts |
Active |
| Friday, May 15, 2026 9:00 am - 12:00 pm | |||
| Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre › Stage / Front of House (Theatre Seating) (CC140A) |
| 18 |
Middle School PE | Active |
|
| Monday, May 18, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 20 |
Middle School PE | Active |
|
| Wednesday, May 20, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 20 |
TAP Setup | Fine Arts |
Active |
| Wednesday, May 20, 2026 3:00 pm - 8:00 pm | |||
| Windermere Preparatory School › Cypress Center for the Arts › Atrium (CC100)Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre |
| 21 |
8th Grade "Turning a Page" Ceremony | Active |
|
| Thursday, May 21, 2026 8:00 am - 9:00 pm | |||
| Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre |
| 22 |
End of Q4 - LAST DAY OF SCHOOL- Early Dismissal | Active |
|
| Friday, May 22, 2026 7:30 am - 12:00 pm | |||
| Windermere Preparatory School › Lower SchoolWindermere Preparatory School › Middle SchoolWindermere Preparatory School › High School |
| 22 |
Middle School PE | Active |
|
| Friday, May 22, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 25 |
Middle School PE | Active |
|
| Monday, May 25, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 27 |
Middle School PE | Active |
|
| Wednesday, May 27, 2026 8:00 am - 2:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
| 29 |
Middle School PE | Active |
|
| Friday, May 29, 2026 8:00 am - 3:00 pm | |||
| Windermere Preparatory School › Middle School › Laker Lounge |
104 Active 2 Cancelled