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| 1 Early Dismissal @ New Trier - All School Calendar Blue Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way)
| 2 Early Dismissal @ New Trier - All School Calendar Green Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way) Fall Jazz Concert 7:00pm-9:00pm (New Trier - Performing Arts) @ Aud - WKA - Gaffney Auditorium
| 3 8th Grade Placement Testing 7:45am-12:45pm @ New Trier Township - Northfield Campus Tri-ship Tree Sale 9:00am-5:00pm @ Winnetka Campus - North Lawn (Trevian Way)
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4 Tri-ship Tree Sale 11:00am-4:00pm @ Winnetka Campus - North Lawn (Trevian Way)
| 5 Blue Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way)
| 6 Green Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way)
| 7 Anchor Day - Semester 1 @ New Trier - All School Calendar High Five Winter Sing 2:15pm-2:50pm (New Trier - Performing Arts) @ Aud - WKA - Gaffney Auditorium (A100) Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way)
| 8 Blue Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way) Freshman Sophomore Musical Workshop 7:00pm-9:00pm (New Trier - Performing Arts) @ Aud - NFD - Cornog Auditorium (E201)
| 9 Green Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way) Freshman Sophomore Musical Workshop 4:30pm-6:30pm (New Trier - Performing Arts) @ Aud - NFD - Cornog Auditorium (E201)
| 10 ACT Testing 7:45am-12:45pm @ New Trier Township - Northfield Campus Tri-ship Tree Sale 9:00am-5:00pm @ Winnetka Campus - North Lawn (Trevian Way) Freshman Sophomore Musical Workshop 2:00pm-4:30pm (New Trier - Performing Arts) @ Aud - NFD - Cornog Auditorium (E201)
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11 Tri-ship Tree Sale 11:00am-4:00pm @ Winnetka Campus - North Lawn (Trevian Way)
| 12 Blue Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way)
| 13 Green Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way)
| 14 Anchor Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way) Winter Play - Performance 7:00pm-9:00pm (New Trier - Performing Arts) @ Aud - WKA - McGee Auditorium (W104)
| 15 Blue Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way) Winter Play - Performance 7:00pm-9:00pm (New Trier - Performing Arts) @ Aud - WKA - McGee Auditorium (W104)
| 16 Green Day - Semester 1 @ New Trier - All School Calendar Tri-ship Tree Sale 4:00pm-7:00pm @ Winnetka Campus - North Lawn (Trevian Way) Winter Play - Performance 4:30pm-6:30pm (New Trier - Performing Arts) @ Aud - WKA - McGee Auditorium (W104)
| 17 Tri-ship Tree Sale 9:00am-5:00pm @ Winnetka Campus - North Lawn (Trevian Way)
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18 Winter Music Festival 2:00pm-3:00pm (New Trier - Performing Arts) @ Aud - WKA - Gaffney Auditorium Winter Music Festival 4:00pm-5:00pm (New Trier - Performing Arts) @ Aud - WKA - Gaffney Auditorium
| 19 First Semester Final Exams @ New Trier - All School Calendar Northfield Student Art Exhibit 8:00am-3:00pm @ Northfield Campus - Cafe/ Lounge (B100A) Board of Education Meeting 5:30pm-10:00pm @ Northfield Campus - Conference Room - Board Room (C234)
| 20 First Semester Final Exams @ New Trier - All School Calendar Northfield Student Art Exhibit 8:00am-3:00pm @ Northfield Campus - Cafe/ Lounge (B100A)
| 21 Institute Day - No School for Students @ New Trier - All School Calendar Northfield Student Art Exhibit 10:30am-3:00pm @ Northfield Campus - Cafe/ Lounge (B100A) Winter Vocal Jazz Concert 7:00pm-9:00pm (New Trier - Performing Arts) @ Aud - WKA - Hayes McCausland Theatre (W022)
| 22 Last Day of First Semester @ New Trier - All School Calendar Early Dismissal @ New Trier - All School Calendar Anchor Day - Semester 1 @ New Trier - All School Calendar Northfield Student Art Exhibit 8:00am-3:00pm @ Northfield Campus - Cafe/ Lounge (B100A)
| 23 Winter Break @ New Trier - All School Calendar
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25 | 26 Winter Break @ New Trier - All School Calendar
| 27 Winter Break @ New Trier - All School Calendar
| 28 Winter Break @ New Trier - All School Calendar
| 29 Winter Break @ New Trier - All School Calendar
| 30 Winter Break @ New Trier - All School Calendar
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