| Index | Chestertown | Maryland | National |
| Average Test Scores | 33% | 40% | 48% |
| Student/Teacher ratio | 14:1 | 16:1 | 16:1 |
| Total public schools | 2 | 1,163 | 79,221 |
| Total private schools | 3 | 674 | 24,874 |
| Total post-secondary schools | 1 | 112 | 7,963 |
| Index | Chestertown | Maryland | National |
| Completed 8th grade | 84.7% | 87.5% | 84.3% |
| Completed high school | 81.9% | 86.5% | 83.0% |
| Completed some college | 60.3% | 64.2% | 59.4% |
| Completed associate degree | 45.4% | 44.8% | 38.5% |
| Completed bachelors | 38.9% | 38.4% | 30.3% |
| Completed masters | 18.9% | 17.7% | 11.5% |
| Completed professional degree | 9.5% | 5.5% | 3.3% |
| Completed doctorate | 5.1% | 2.5% | 1.3% |
There are a total of 2 public schools, 3 private schools and 1 post-secondary schools in Chestertown. Using the proficiency score averages, the average test scores for Chestertown, MD schools is 33%. The average student to teacher ratio is 14:1. In Chestertown, MD, an average of 84.7% of students have completed 8th grade and an average of 81.9% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Centreville, MD | 4,829 | 60% | 24.0% |
| Church Hill, MD | 866 | 57% | 18.8% |
| Worton, MD | 98 | 52% | 8.3% |
| Cecilton, MD | 901 | 42% | 12.5% |
| Sudlersville, MD | 423 | 42% | 13.0% |
| Chestertown, MD | 5,073 | 33% | 31.8% |
| City | Population | Avg. Test Scores | National Avg. |
| Holbrook, AZ | 5,073 | 37% | 22.3% |
| Penn Yan, NY | 5,072 | 60% | 24.7% |
| Creve Coeur, IL | 5,074 | 10% | 79.2% |
| Vinton, IA | 5,075 | 80% | 66.0% |
| Montevideo, MN | 5,071 | 48% | 0.5% |
| Chestertown, MD | 5,073 | 33% | 31.8% |
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