| | Chestertown, MD | Bristol, CT | United States |
| Population | 5,557 | 60,733 | 329,725,481 |
| Female Population | 53.8% | 51.1% | 50.5% |
| Male Population | 46.2% | 48.9% | 49.5% |
| Median Age | 39.1 | 40.2 | 38.4 |
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| Population - 2010 | 5,281 | 60,495 | 309,327,143 |
| Population - 2000 | 4,746 | 60,062 | 285,036,114 |
| Population - 1990 | 4,005 | 60,640 | 251,960,433 |
| Pop. 2000 to Now | 5.4% | -0.6% | 15.6% |
| Pop. 1990 to Now | 24.9% | -1.5% | 30.8% |
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| Population Density | 2,016.3 | 2,300.0 | 93.4 |
| Land Area | 2.8 | 26.4 | 3,531,905.4 |
| Water Area | 0.3 | 0.4 | 264,836.8 |
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| Est. Total Population By Age | | | |
| | Chestertown, MD | Bristol, CT | United States |
| Age 0 to 4 | 3.1% | 4.3% | 5.9% |
| Age 5 to 9 | 3.5% | 6.2% | 6.1% |
| Age 10 to 14 | 1.5% | 6.8% | 6.6% |
| Age 15 to 17 | 5.4% | 3.8% | 3.9% |
| Age 18 to 20 | 18.3% | 3.3% | 4.0% |
| Age 21 to 24 | 9.5% | 4.6% | 5.2% |
| Age 25 to 34 | 7.2% | 13.1% | 13.8% |
| Age 35 to 44 | 6.2% | 13.4% | 12.9% |
| Age 45 to 54 | 9.2% | 14.0% | 12.6% |
| Age 55 to 59 | 4.1% | 6.9% | 6.7% |
| Age 60 to 64 | 6.6% | 7.0% | 6.3% |
| Age 65 to 74 | 10.7% | 9.6% | 9.6% |
| Age 75 to 84 | 8.0% | 4.7% | 4.5% |
| Age 85 and over | 6.7% | 2.4% | 1.9% |
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| Race | | | |
| | Chestertown, MD | Bristol, CT | United States |
| White | 70.9% | 71.8% | 59.4% |
| Black | 21.4% | 5.4% | 12.2% |
| Asian | 2.6% | 1.5% | 5.6% |
| Native American | 0.0% | 0.1% | 0.6% |
| Hawaiian, Pacific Islander | 0.0% | 0.0% | 0.2% |
| Other | 0.0% | 0.4% | 0.4% |
| Two or More Races | 2.1% | 3.4% | 3.2% |
| Hispanic | 2.9% | 17.4% | 18.4% |
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| Marriage & Family | | | |
| | Chestertown, MD | Bristol, CT | United States |
| Married Population | 24.7% | 47.4% | 49.8% |
| Currently Married | 21.1% | 46.2% | 48.0% |
| Married but Separated | 3.6% | 1.2% | 1.8% |
| Single Population | 75.3% | 52.6% | 50.2% |
| Never Married | 50.9% | 33.8% | 33.8% |
| Divorced | 9.9% | 12.8% | 10.8% |
| Widowed | 14.5% | 6.1% | 5.6% |
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| Household Size | 1.73 | 2.44 | 2.60 |
| Households | 2,365 | 24,566 | 124,010,992 |
| Family Households | 1,112 | 15,637 | 80,755,759 |
| Married couple, w/children | 10.6% | 26.9% | 30.5% |
| Married couple, no children | 37.2% | 42.0% | 42.9% |
| Non Family Households | 1,253 | 8,929 | 43,255,233 |
| Single householder, w/children | 34.0% | 19.1% | 15.8% |
| Single householder, no children | 18.2% | 12.0% | 10.8% |