Class of 2010
- The Marvelwood School
- Westover School
- Immaculate Catholic
- Pawling High School (3)
- Canterbury School
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Class of 2009
- Canterbury School
- Avon Old Farms School (2)
- Pawling High School
- Poughkeepsie Day School
- John F. Kennedy Catholic (3)
- Dover High School
- The Harvey School
- Marvelwood School
- The Wooster School
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Class of 2008
- Trinity Pawling School (3)
- Wooster School
- Pawling High School
- Millbrook School
- Kent School
- Canterbury School (6)
- Immaculate High School (2)
- St. Scholastica Academy (LA)
- Burke Academy (VT)
- The Harvey School
- Hotchkiss School
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Class of 2007
- The Putney School
- South Kent
- Oakwood Friends School
- Trinity-Pawling School (2)
- Poughkeepsie Day School
- Millbrook School (2)
- John F. Kennedy Catholic High School
- Canterbury School (2)
- Our Lady of Lourdes Catholic High School (2)
- Brewster High School (2)
- Kent School
- The Gunnery
- South Jefferson Central School
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Class of 2006
- J.F Kennedy Catholic High School
- Canterbury School (7)
- Kent School (3)
- Brewster High School
- Hotchkiss School
- Millbrook School
- Marvelwood School
- Oakwood Friends School
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Colleges
- Pace University
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Mount Holyoke College
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Quinnipiac University
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Salve Reginia University
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Syracuse University
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SUNY at Stony Brooke
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The University of Scranton
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Vassar College
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Colgate
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Bates College
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LSU
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SUNY at Oneonta
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Hamilton College
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Class of 2005
- Pawling High School (2)
- J.F. Kennedy Catholic High School (3)
- Hotchkiss School
- Millbrook School (2)
- Carmel High School
- Canterbury School (2)
- Millbrook Public High School
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Colleges
- Princeton
- Sacred Heart University
- Western CT State University
- Hobart & William Smith
- Roger Williams
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Class of 2004 - Our First Graduating Class
- Wooster School
- The Harvey School
- Canterbury School
- Institute for Collaborative Education, NYC
- J.F. Kennedy Catholic High School
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Colleges
- Loyola College (MD)
- Northeastern University (MA)
- Saint Joseph University (PA)
- SUNY Cobleskill
- Western CT State University
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