| Index | Cheshire | Massachusetts | National |
| Average Test Scores | 32% | 52% | 48% |
| 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 32%. 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 | Population | Avg. Test Scores | National Avg. |
| Lenox, MA | 1,984 | 69% | 43.8% |
| Williamstown, MA | 4,565 | 67% | 39.1% |
| Adams, MA | 5,689 | 47% | 3.1% |
| North Adams, MA | 12,897 | 37% | 23.5% |
| Pittsfield, MA | 42,514 | 36% | 24.9% |
| Cheshire, MA | 683 | 32% | 34.4% |
| City | Population | Avg. Test Scores | National Avg. |
| Mathews, VA | 683 | 78% | 61.5% |
| Smiths Grove, KY | 683 | 52% | 8.9% |
| Carbonado, WA | 683 | 77% | 60.4% |
| Colman, SD | 683 | 44% | 8.3% |
| Wilson, KS | 683 | 40% | 16.7% |
| Cheshire, MA | 683 | 32% | 34.4% |
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