| Index | Winchendon | Massachusetts | National |
| Average Test Scores | 37% | 52% | 48% |
| Student/Teacher ratio | 13:1 | 14:1 | 16:1 |
| Total public schools | 3 | 1,167 | 79,221 |
| Total private schools | 1 | 508 | 24,874 |
| Total post-secondary schools | n/a | 193 | 7,963 |
| Index | Winchendon | Massachusetts | National |
| Completed 8th grade | 76.3% | 88.3% | 84.3% |
| Completed high school | 75.4% | 87.2% | 83.0% |
| Completed some college | 40.4% | 65.0% | 59.4% |
| Completed associate degree | 22.5% | 49.0% | 38.5% |
| Completed bachelors | 13.5% | 41.2% | 30.3% |
| Completed masters | 4.7% | 18.2% | 11.5% |
| Completed professional degree | 0.4% | 5.4% | 3.3% |
| Completed doctorate | 0.4% | 2.6% | 1.3% |
There are a total of 3 public schools, 1 private schools and n/a post-secondary schools in Winchendon. Using the proficiency score averages, the average test scores for Winchendon, MA schools is 37%. The average student to teacher ratio is 13:1. In Winchendon, MA, an average of 76.3% of students have completed 8th grade and an average of 75.4% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| South Ashburnham, MA | 883 | 55% | 14.1% |
| Petersham, MA | 256 | 50% | 3.1% |
| Jaffrey, NH | 2,750 | 50% | 3.1% |
| Peterborough, NH | 2,704 | 49% | 2.4% |
| Leominster, MA | 41,581 | 48% | 0.1% |
| Winchendon, MA | 4,673 | 37% | 22.2% |
| City | Population | Avg. Test Scores | National Avg. |
| Little Falls, NY | 4,673 | 55% | 13.5% |
| Ellisville, MS | 4,671 | 47% | 2.1% |
| Eldon, MO | 4,671 | 51% | 6.0% |
| Mount Olive, NC | 4,670 | 28% | 42.7% |
| Clinton, IN | 4,679 | 39% | 19.2% |
| Winchendon, MA | 4,673 | 37% | 22.2% |
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