| Sept. 6, '09
| | 100 Years of Inspiring Design - Exhibit Opening |
| Sept. 24 | | "An Evening with Dr. Gina Barreca," 5:30 to 7:30 pm, sponsored by the Women's Initiative Fund of the Ct Community Foundation |
| Sept. 24 | | Ninth graders to Hill-Stead Museum, 12:15 to 4:30 pm |
| Sept. 25
| | Nadia Birkenstock '92, celtic harpist, 7:30 to 9 pm |
| Oct. 9
| | Mihae Lee '76 and Hae-soon Hahn '78, piano and violin, 7:30 to 9 pm
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| Oct. 18 | | C.O.L.O.R.E.S. Festival in the afternoon |
| Oct. 25 | | "100 Years of Inspiring Sculpture" - Exhibit Opening |
| Oct. 30 | | Student Performances for Parents' Weekend, late afternoon |
| Nov. 6/7 | | "The 25th Annual Putnam County Spelling Bee," Fall Musical, 7:30 pm |
| Dec. 4 | | Yoonie Choi '97 and Lane Summers Moorman '93 , cello, 7:30 to 9 pm |
| Dec. 11 | | Candlelight Service of Lessons and Carols, 7:30 pm, Chapel
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| Dec. 12 | | Candlelight Service of Lessons and Carols, 8 pm, Chapel
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| Dec. 13 | | Candlelight Service of Lessons and Carols, 3:30 pm, Chapel
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| Jan. 7 '10
| | "100 Years of Inspiring Videography" - Exhibit Opening |
| Jan. 10 | | Dorcas Charity Fair run by Junior Class, Fuller Athletic Center
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| Jan. 25
| | Music master classes, 7 pm
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| Jan. 30 | | International Film Festival for students, sponsored by the Social Committee
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| Jan. 31 | | "100 Years of Inspiring Works on Paper" - Exhibit Opening |
| Jan. 31
| | Trinity Pawling Joint Concert, 4:30 pm in Chapel
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| Feb. 1
| | Music master classes, Part II, 7:30 pm
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| Feb. 12/13
| | "The Diary of Anne Frank," Winter Drama performance, 7:30 pm
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| Feb. 19 | | Music Fundraiser Concert, 7:30 pm
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| Mar.19-22 | | West and Over German rehearsals and performances |
| Mar. 28 | | "100 Years of Inspiring Painting" - Exhibit Opening |
| April 30 | | Annual Spring Dance Concert, 7:30 pm - Guest appearance by Elise Drew '93
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| May 7/8 | | "JUST THINK!, A Tribute to Westover Past and Present" performance - 7:30 pm |
| May 21 | | Cabaret Performance by Renee Bang Allen '86, 7:30 to 9 pm |
| May 24/25 | | Student music recitals, 7 pm, in chapel |
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