| Index | Cheshire | Massachusetts | National |
| Average Test Scores | 54% | 64% | 49% |
| Student/Teacher ratio | n/a | 14:1 | 16:1 |
| Total public schools | n/a | 1,167 | 79,221 |
| Total private schools | n/a | 508 | 24,874 |
| Total post-secondary schools | n/a | 193 | 7,963 |
| Index | Cheshire | Massachusetts | National |
| Completed 8th grade | 89.4% | 88.3% | 84.3% |
| Completed high school | 86.3% | 87.2% | 83.0% |
| Completed some college | 63.8% | 65.0% | 59.4% |
| Completed associate degree | 33.2% | 49.0% | 38.5% |
| Completed bachelors | 16.7% | 41.2% | 30.3% |
| Completed masters | 0.0% | 18.2% | 11.5% |
| Completed professional degree | 0.0% | 5.4% | 3.3% |
| Completed doctorate | 0.0% | 2.6% | 1.3% |
There are a total of n/a public schools, n/a private schools and n/a post-secondary schools in Cheshire. Using the proficiency score averages, the average test scores for Cheshire, MA schools is 54%. The average student to teacher ratio is n/a. In Cheshire, MA, an average of 89.4% of students have completed 8th grade and an average of 86.3% have completed high school.
| City, State | Population | Avg. Test Scores | National Avg. |
| Williamstown, MA | 4,315 | 80% | 63% |
| Lenox, MA | 1,833 | 77% | 56% |
| North Adams, MA | 13,326 | 57% | 17% |
| Adams, MA | 5,412 | 57% | 15% |
| Pittsfield, MA | 43,632 | 51% | 4% |
| Cheshire, MA | 647 | 54% | 9% |
| City, State | Population | Avg. Test Scores | National Avg. |
| White Hall, WV | 647 | 72% | 46% |
| Groom, TX | 647 | 75% | 52% |
| Hamler, OH | 647 | 83% | 68% |
| Graceville, MN | 647 | 58% | 18% |
| Harrah, WA | 647 | 19% | 62% |
| Cheshire, MA | 647 | 54% | 9% |
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