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

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

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

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

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

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

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

7	The biggest best roller coaster day	Middle School	Active
	Friday,  November  7,  2025  7:00 am - 3:30 pm
	Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre

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

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

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

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

17	Lifetouch Picture Retake Day	Middle School Lower School High School	Active
	Monday,  November  17,  2025  7:30 am - 3:30 pm
	Windermere Preparatory School › Athletics › Gym

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

18	End of Q2 - Early Dismissal Day		Active
	Thursday,  December  18,  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  19,  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  19,  2025  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

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

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

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

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

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

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

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

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

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

12	Middle School PE		Active
	Monday,  January  12,  2026  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

13	MS Q2 Celebration	Middle School	Active
	Tuesday,  January  13,  2026  2:00 pm - 3:00 pm
	Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre

14	Middle School PE		Active
	Wednesday,  January  14,  2026  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

16	Middle School PE		Active
	Friday,  January  16,  2026  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

19	MLK Jr Day - NO SCHOOL		Active
	Monday,  January  19,  2026  7:00 am - 3:00 pm
	Windermere Preparatory School › Middle School Windermere Preparatory School › Lower School Windermere Preparatory School › High School

19	Middle School PE		Active
	Monday,  January  19,  2026  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

20	Learning Buddies		Active
	Tuesday,  January  20,  2026  2:30 pm - 3:30 pm
	Windermere Preparatory School › Middle School

21	Middle School PE		Active
	Wednesday,  January  21,  2026  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

23	7th Grade Sustainability Field Trip - Animal Kingdom		Active
	Friday,  January  23,  2026  7:30 am - 4:00 pm
	Disney's Animal Kingdom Theme Park

23	Middle School PE		Active
	Friday,  January  23,  2026  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

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

3	MS Book Author Presentation	Middle School	Active
	Tuesday,  February  3,  2026  8:00 am - 11:00 am
	Windermere Preparatory School › Cypress Center for the Arts › Dr. Thomas L. Marcy Theatre

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	Athletics High School Lower School Middle School Fine Arts	Active
	Saturday,  February  7,  2026  (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

9	Middle School PE		Active
	Monday,  February  9,  2026  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

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

18	Middle School PE		Active
	Wednesday,  February  18,  2026  8:00 am - 2:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge

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

27	Middle School PE		Active
	Friday,  February  27,  2026  8:00 am - 3:00 pm
	Windermere Preparatory School › Middle School › Laker Lounge