Aug

24

to Aug 25

Locker Days

• Mon, Aug 24, 2026 9:00 AM Tue, Aug 25, 2026 12:00 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Aug

26

Freshman Orientation

• Wednesday, August 26, 2026
• 7:45 AM 1:00 PM
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Aug

27

to Aug 28

Retreat

• Thu, Aug 27, 2026 7:45 AM Fri, Aug 28, 2026 4:00 PM
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Aug

28

Feast of St. Augustine

• Friday, August 28, 2026
• 12:00 AM 11:59 PM
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Sep

4

Picture Day

• Friday, September 4, 2026
• 7:45 AM 3:15 PM
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Sep

7

Labor Day

• Monday, September 7, 2026
• 12:00 AM 11:59 PM
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Sep

10

Back to School Night

• Thursday, September 10, 2026
• 5:30 PM 7:30 PM
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Sep

13

Feast of St. Chrysostom

• Sunday, September 13, 2026
• 12:00 AM 11:59 PM
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Sep

17

Convocation/Field Day #1

• Thursday, September 17, 2026
• 7:45 AM 3:15 PM
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Sep

29

Ora Et Labora

• Tuesday, September 29, 2026
• 7:45 AM 1:00 PM
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Oct

6

9th Grade Convocation

• Tuesday, October 6, 2026
• 8:45 AM 9:28 PM
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Oct

8

Conferences Day 1

• Thursday, October 8, 2026
• 1:30 PM 7:00 PM
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Oct

9

Conferences Day 2

• Friday, October 9, 2026
• 9:00 AM 2:00 PM
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Oct

13

10th Grade Convocation

• Tuesday, October 13, 2026
• 8:45 AM 9:28 AM
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Oct

18

Open House

• Sunday, October 18, 2026
• 1:00 PM 2:30 PM
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Oct

23

Fall Dance

• Friday, October 23, 2026
• 7:00 PM 10:00 PM
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Nov

3

11th Grade Convocation

• Tuesday, November 3, 2026
• 8:45 AM 9:28 AM
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Nov

12

to Nov 14

Sophomore Play

• Thu, Nov 12, 2026 12:00 AM Sat, Nov 14, 2026 11:59 PM
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Nov

17

Capstone Exam Day (12th Grade)

• Tuesday, November 17, 2026
• 7:45 AM 3:15 PM
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Nov

25

to Nov 27

Thanksgiving Break

• Wed, Nov 25, 2026 12:00 AM Fri, Nov 27, 2026 11:59 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Dec

3

Convocation/Field Day #2

• Thursday, December 3, 2026
• 7:45 AM 3:15 PM
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Dec

7

Feast of St. Ambrose

• Monday, December 7, 2026
• 12:00 AM 11:59 PM
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Dec

11

Advent Concert

• Friday, December 11, 2026
• 6:30 PM 9:00 PM
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Dec

18

to Jan 1

Christmas Break

• Fri, Dec 18, 2026 12:00 AM Fri, Jan 1, 2027 11:59 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Dec

19

Alumni Basketball Game

• Saturday, December 19, 2026
• 12:00 AM 11:59 PM
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Jan

4

First Day of Second Semester

• Monday, January 4, 2027
• 7:45 AM 3:15 PM
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Jan

8

Senior Capstone Day

• Friday, January 8, 2027
• 7:45 AM 3:15 PM
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Jan

14

to Jan 16

Junior Play

• Thu, Jan 14, 2027 12:00 AM Sat, Jan 16, 2027 11:59 PM
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Jan

20

Senior Retreat

• Wednesday, January 20, 2027
• 7:45 AM 3:15 PM
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Feb

5

Gala Practice

• Friday, February 5, 2027
• 12:00 AM 11:59 PM
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Feb

6

2027 Gala

• Saturday, February 6, 2027
• 12:00 AM 11:59 PM
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Feb

10

Ash Wednesday

• Wednesday, February 10, 2027
• 12:00 AM 11:59 PM
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Feb

18

to Feb 19

Winter Break

• Thu, Feb 18, 2027 12:00 AM Fri, Feb 19, 2027 11:59 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Feb

26

National Latin Exam

• Friday, February 26, 2027
• 7:45 AM 3:15 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Mar

4

Convocation/Field Day #3

• Thursday, March 4, 2027
• 7:45 AM 3:15 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Mar

9

ACT (11th)

• Tuesday, March 9, 2027
• 7:45 AM 3:15 PM
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Mar

10

Pre-ACT (10th)

• Wednesday, March 10, 2027
• 7:45 AM 3:15 PM
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Mar

12

Early Release

• Friday, March 12, 2027
• 7:45 AM 1:00 PM
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Mar

12

Conferences

• Friday, March 12, 2027
• 2:00 PM 7:00 PM
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Mar

22

to Apr 2

Rome Pilgrimage (12th)

• Mon, Mar 22, 2027 12:00 AM Fri, Apr 2, 2027 11:59 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Mar

25

to Apr 2

Easter Break

• Thu, Mar 25, 2027 12:00 AM Fri, Apr 2, 2027 11:59 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Apr

6

CLT (11th)

• Tuesday, April 6, 2027
• 7:45 AM 3:15 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Apr

15

to Apr 17

Senior Play

• Thu, Apr 15, 2027 12:00 AM Sat, Apr 17, 2027 11:59 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Apr

21

CLT 10 (10th)

• Wednesday, April 21, 2027
• 7:45 AM 3:15 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Apr

23

Early Release

• Friday, April 23, 2027
• 7:45 AM 1:00 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Apr

26

to Apr 30

Spring Week

• Mon, Apr 26, 2027 7:45 AM Fri, Apr 30, 2027 3:15 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Apr

27

Career Day

• Tuesday, April 27, 2027
• 7:45 AM 3:15 PM
• Chesterton Academy of Milwaukee Inc. (map)
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Apr

29

Convocation/Field Day #4

• Thursday, April 29, 2027
• 7:45 AM 3:15 PM
• Chesterton Academy of Milwaukee Inc. (map)
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May

1

Spring Formal

• Saturday, May 1, 2027
• 12:00 AM 11:59 PM
• Chesterton Academy of Milwaukee Inc. (map)
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May

2

Feast of St. Athanasius

• Sunday, May 2, 2027
• 12:00 AM 11:59 PM
• Chesterton Academy of Milwaukee Inc. (map)
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May

5

Senior Day & Dinner

• Wednesday, May 5, 2027
• 12:00 AM 11:59 PM
• Chesterton Academy of Milwaukee Inc. (map)
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May

14

Early Release

• Friday, May 14, 2027
• 7:45 AM 1:00 PM
• Chesterton Academy of Milwaukee Inc. (map)
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May

14

Fine Arts Festival

• Friday, May 14, 2027
• 6:00 PM 11:00 PM
• Chesterton Academy of Milwaukee Inc. (map)
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May

21

The Last Lecture 2027

• Friday, May 21, 2027
• 2:32 PM 3:15 PM
• Chesterton Academy of Milwaukee Inc. (map)
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May

26

Last Day (12th)

• Wednesday, May 26, 2027
• 7:45 AM 3:15 PM
• Chesterton Academy of Milwaukee Inc. (map)
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May

26

Prefect Ceremony

• Wednesday, May 26, 2027
• 8:45 AM 9:30 AM
• Chesterton Academy of Milwaukee Inc. (map)
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May

27

Last Day (9th-11th)

• Thursday, May 27, 2027
• 7:45 AM 3:15 PM
• Chesterton Academy of Milwaukee Inc. (map)
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May

28

Graduation

• Friday, May 28, 2027
• 6:00 PM 9:00 PM
• Chesterton Academy of Milwaukee Inc. (map)
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