America's Most Challenging Schools By State: Massachusetts
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| Recognized By: | The Washington Post |
| Publication Date: | April 2014 |
| Number of Honorees: | 13 |
Businesses Receiving This Recognition
| Bancroft School | |
| Bellingham School District | |
| Deerfield Academy | Deerfield, MA |
| East Longmeadow High School | MA |
| Foxborough High School | Foxborough, MA |
| Greenfield High School | Greenfield, MA |
| Melrose Public Schools | MA |
| Newton South High School | Newton, MA |
| Northbridge Public Schools | Whitinsville, MA |
| Quincy Upper School | Boston, MA |
| Rockport High School | Rockport, MA |
| The Rivers School | |
| Winchester Public Schools |
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