| | Middlebury, VT | Winsted, CT | United States |
| Population | 9,029 | 6,662 | 329,725,481 |
| Female Population | 51.2% | 50.1% | 50.5% |
| Male Population | 48.8% | 49.9% | 49.5% |
| Median Age | 28.6 | 44.1 | 38.4 |
| space3 | | | |
| Population - 2010 | 8,493 | 7,318 | 309,327,143 |
| Population - 2000 | 8,183 | 7,321 | 285,036,114 |
| Population - 1990 | 8,034 | 8,254 | 251,960,433 |
| Pop. 2000 to Now | 7.3% | -0.3% | 15.6% |
| Pop. 1990 to Now | 9.3% | -11.6% | 30.8% |
| space4 | | | |
| Population Density | 232.5 | 1,441.4 | 93.4 |
| Land Area | 38.8 | 4.6 | 3,531,905.4 |
| Water Area | 0.4 | 0.2 | 264,836.8 |
| space | | | |
| Est. Total Population By Age | | | |
| | Middlebury, VT | Winsted, CT | United States |
| Age 0 to 4 | 2.3% | 2.2% | 5.9% |
| Age 5 to 9 | 3.7% | 7.1% | 6.1% |
| Age 10 to 14 | 4.5% | 3.7% | 6.6% |
| Age 15 to 17 | 1.4% | 2.6% | 3.9% |
| Age 18 to 20 | 23.7% | 3.8% | 4.0% |
| Age 21 to 24 | 11.6% | 3.5% | 5.2% |
| Age 25 to 34 | 7.4% | 10.9% | 13.8% |
| Age 35 to 44 | 9.5% | 17.1% | 12.9% |
| Age 45 to 54 | 7.0% | 8.7% | 12.6% |
| Age 55 to 59 | 3.0% | 6.4% | 6.7% |
| Age 60 to 64 | 6.1% | 12.1% | 6.3% |
| Age 65 to 74 | 9.9% | 13.5% | 9.6% |
| Age 75 to 84 | 5.3% | 4.8% | 4.5% |
| Age 85 and over | 4.4% | 3.7% | 1.9% |
| space1 | | | |
| Race | | | |
| | Middlebury, VT | Winsted, CT | United States |
| White | 81.9% | 87.2% | 59.4% |
| Black | 3.3% | 1.7% | 12.2% |
| Asian | 5.8% | 0.0% | 5.6% |
| Native American | 0.1% | 0.5% | 0.6% |
| Hawaiian, Pacific Islander | 0.0% | 0.0% | 0.2% |
| Other | 0.0% | 0.0% | 0.4% |
| Two or More Races | 4.9% | 3.1% | 3.2% |
| Hispanic | 4.0% | 7.5% | 18.4% |
| space2 | | | |
| Marriage & Family | | | |
| | Middlebury, VT | Winsted, CT | United States |
| Married Population | 34.1% | 42.0% | 49.8% |
| Currently Married | 33.5% | 39.8% | 48.0% |
| Married but Separated | 0.5% | 2.2% | 1.8% |
| Single Population | 65.9% | 58.0% | 50.2% |
| Never Married | 53.5% | 36.9% | 33.8% |
| Divorced | 7.1% | 16.0% | 10.8% |
| Widowed | 5.4% | 5.0% | 5.6% |
| space5 | | | |
| Household Size | 2.09 | 2.04 | 2.60 |
| Households | 2,875 | 3,250 | 124,010,992 |
| Family Households | 1,580 | 1,536 | 80,755,759 |
| Married couple, w/children | 26.3% | 25.9% | 30.5% |
| Married couple, no children | 57.5% | 49.9% | 42.9% |
| Non Family Households | 1,295 | 1,714 | 43,255,233 |
| Single householder, w/children | 8.9% | 14.8% | 15.8% |
| Single householder, no children | 7.3% | 9.4% | 10.8% |