5	Middle School PE	PE	Active
	Friday  September  5th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

5	7th Grade Library Orientation	7th Grade	Active
	Friday  September  5th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Learning Commons

8	8th Grade Library Orientation	Middle School	Active
	Monday  September  8th  2025  8:00 am - 3:10 pm
	Windermere Preparatory School › Learning Commons

8	Middle School PE		Active
	Monday  September  8th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

10	Middle School PE		Active
	Wednesday  September  10th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

11	MS Fall Book Fair Set Up	Middle School	Active
	Thursday  September  11th  2025  8:00 am - 11:00 am
	Windermere Preparatory School › Learning Commons

11	MS Book Club	Middle School	Active
	Thursday  September  11th  2025  11:50 am - 12:20 pm
	Windermere Preparatory School › Learning Commons

12	MS Fall Book Fair	Middle School	Active
	Friday  September  12th  2025  (All Day)
	Windermere Preparatory School › Learning Commons

12	Middle School PE		Active
	Friday  September  12th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

15	MS Fall Book Fair	Middle School	Active
	Monday  September  15th  2025  (All Day)
	Windermere Preparatory School › Learning Commons

15	Middle School PE		Active
	Monday  September  15th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

16	MS Fall Book Fair	Middle School	Active
	Tuesday  September  16th  2025  (All Day)
	Windermere Preparatory School › Learning Commons

17	MS Fall Book Fair	Middle School	Active
	Wednesday  September  17th  2025  (All Day)
	Windermere Preparatory School › Learning Commons

17	Middle School PE		Active
	Wednesday  September  17th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

18	MS Fall Book Fair	Middle School	Active
	Thursday  September  18th  2025  (All Day)
	Windermere Preparatory School › Learning Commons

19	MS Fall Book Fair	Middle School	Active
	Friday  September  19th  2025  (All Day)
	Windermere Preparatory School › Learning Commons

19	Conference Day - NO SCHOOL		Active
	Friday  September  19th  2025  7:30 am - 3:00 pm
	Windermere Preparatory School › Middle School Windermere Preparatory School › High School Windermere Preparatory School › Lower School

19	Middle School PE		Active
	Friday  September  19th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

22	Middle School PE		Active
	Monday  September  22nd  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

24	Middle School PE		Active
	Wednesday  September  24th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

25	MS Book Club	Middle School	Active
	Thursday  September  25th  2025  11:50 am - 12:20 pm
	Windermere Preparatory School › Learning Commons

26	Middle School PE		Active
	Friday  September  26th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

29	6th Grade Orlando Family Stage - Goosebumps		Active
	Monday  September  29th  2025  8:00 am - 2:00 pm
	Orlando Repertory Theatre

29	Middle School PE		Active
	Monday  September  29th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

1	Middle School PE		Active
	Wednesday  October  1st  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

2	MS Book Club	Middle School	Active
	Thursday  October  2nd  2025  11:50 am - 12:20 pm
	Windermere Preparatory School › Learning Commons

3	Middle School PE		Active
	Friday  October  3rd  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

4	Admissions - Prospective Families Open House	Athletics High School Lower School Middle School Fine Arts	Active
	Saturday  October  4th  2025  (8:00 am) 9:30 am - 11:30 am (1:00 pm)
	Windermere Preparatory School › Middle School › Laker Lounge Windermere Preparatory School › Learning Commons Windermere Preparatory School › Cypress Center for the Arts › Atrium (CC100) Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre

6	Lifetouch Picture Day	Lower School Middle School High School	Active
	Monday  October  6th  2025  6:30 am - 3:30 pm
	Windermere Preparatory School › Athletics › Gym

6	Middle School PE		Active
	Monday  October  6th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

8	End of Q1 - Early Dismissal Day		Active
	Wednesday  October  8th  2025  7:30 am - 12:00 pm
	Windermere Preparatory School › Lower School Windermere Preparatory School › Middle School Windermere Preparatory School › High School

8	Middle School PE		Active
	Wednesday  October  8th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

10	Middle School PE		Active
	Friday  October  10th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

13	Middle School PE		Active
	Monday  October  13th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

14	Spirit Week		Active
	Tuesday  October  14th  2025  12:00 pm - 1:00 pm
	Windermere Preparatory School › High School Windermere Preparatory School › Middle School Windermere Preparatory School › Lower School

15	Middle School PE		Active
	Wednesday  October  15th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

15	Spirit Week		Active
	Wednesday  October  15th  2025  12:00 pm - 1:00 pm
	Windermere Preparatory School › Lower School Windermere Preparatory School › Middle School Windermere Preparatory School › High School

16	MS Book Club	Middle School	Active
	Thursday  October  16th  2025  11:50 am - 12:20 pm
	Windermere Preparatory School › Learning Commons

16	Spirit Week		Active
	Thursday  October  16th  2025  12:00 pm - 1:00 pm
	Windermere Preparatory School › Lower School Windermere Preparatory School › Middle School Windermere Preparatory School › High School

17	Middle School PE		Active
	Friday  October  17th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

17	Spirit Week		Active
	Friday  October  17th  2025  12:00 pm - 1:00 pm
	Windermere Preparatory School › Lower School Windermere Preparatory School › Middle School Windermere Preparatory School › High School

20	Middle School PE		Active
	Monday  October  20th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

22	Middle School PE		Active
	Wednesday  October  22nd  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

23	MS Book Club	Middle School	Active
	Thursday  October  23rd  2025  11:50 am - 12:20 pm
	Windermere Preparatory School › Learning Commons

24	Middle School PE		Active
	Friday  October  24th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

27	Middle School PE		Active
	Monday  October  27th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

28	7th Create-A-Candidate		Active
	Tuesday  October  28th  2025  2:00 pm - 3:00 pm
	Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre

29	Middle School PE		Active
	Wednesday  October  29th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

31	Middle School PE		Active
	Friday  October  31st  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

31	MS/LS "Greet & Treat"	Lower School Middle School	Active
	Friday  October  31st  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School

3	Middle School PE		Active
	Monday  November  3rd  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

5	Middle School PE		Active
	Wednesday  November  5th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

7	Middle School PE		Active
	Friday  November  7th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

10	Middle School PE		Active
	Monday  November  10th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

12	Middle School PE		Active
	Wednesday  November  12th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

14	Middle School PE		Active
	Friday  November  14th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

17	Middle School PE		Active
	Monday  November  17th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

18	Rising 9- Parent Meeting		Active
	Tuesday  November  18th  2025  7:45 am - 9:00 am
	Windermere Preparatory School › Learning Commons

18	Learning Buddies	Middle School	Active
	Tuesday  November  18th  2025  2:00 pm - 3:00 pm
	Windermere Preparatory School › Middle School › MS Classrooms

18	Rising 9- Parent Meeting		Active
	Tuesday  November  18th  2025  6:00 pm - 7:00 pm
	Windermere Preparatory School › Learning Commons

19	Middle School PE		Active
	Wednesday  November  19th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

20	NJAHS Empty Bowls for Hunger		Active
	Thursday  November  20th  2025  11:00 am - 1:00 pm
	Windermere Preparatory School › Middle School › MS Classrooms

21	Middle School PE		Active
	Friday  November  21st  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

21	6th Grade Community Service - Long & Scott Farm		Active
	Friday  November  21st  2025  8:00 am - 3:00 pm
	Long and Scott Farm, Mt. Dora

24	Middle School PE		Active
	Monday  November  24th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

26	Middle School PE		Active
	Wednesday  November  26th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

28	Middle School PE		Active
	Friday  November  28th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

1	Middle School PE		Active
	Monday  December  1st  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

1	MS Holiday Brunch	Middle School	Active
	Monday  December  1st  2025  9:00 am - 11:00 am
	Windermere Preparatory School › Middle School › Laker Lounge

2	6th Grade Spirit of Unitas		Active
	Tuesday  December  2nd  2025  8:00 am  to Thursday  December  4th  2025  4:00 pm
	DaySpring Episcopal Conference Center

3	Middle School PE		Active
	Wednesday  December  3rd  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

5	Middle School PE		Active
	Friday  December  5th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

8	Middle School PE		Active
	Monday  December  8th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

10	Middle School PE		Active
	Wednesday  December  10th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

12	Middle School PE		Active
	Friday  December  12th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

15	Middle School PE		Active
	Monday  December  15th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

17	Middle School PE		Active
	Wednesday  December  17th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

18	End of Q2 - Early Dismissal Day		Active
	Thursday  December  18th  2025  7:30 am - 12:00 pm
	Windermere Preparatory School › Middle School Windermere Preparatory School › High School Windermere Preparatory School › Lower School

19	No School - Teacher Work Day		Active
	Friday  December  19th  2025  7:30 am - 3:00 pm
	Windermere Preparatory School › Lower School Windermere Preparatory School › Middle School Windermere Preparatory School › High School

19	Middle School PE		Active
	Friday  December  19th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

22	Middle School PE		Active
	Monday  December  22nd  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

24	Middle School PE		Active
	Wednesday  December  24th  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

26	Middle School PE		Active
	Friday  December  26th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

29	Middle School PE		Active
	Monday  December  29th  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

31	Middle School PE		Active
	Wednesday  December  31st  2025  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

2	Middle School PE		Active
	Friday  January  2nd  2026  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

5	Middle School PE		Active
	Monday  January  5th  2026  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

7	Middle School PE		Active
	Wednesday  January  7th  2026  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

9	Middle School PE		Active
	Friday  January  9th  2026  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge