| Year | Won | Margin | Democratic | Republican | Total |
|---|---|---|---|---|---|
| 2024 | D | 12,005 | 7,830 | 20,726 | |
| 2020 | D | 12,705 | 7,114 | 20,462 | |
| 2016 | D | 9,539 | 5,925 | 17,381 | |
| 2012 | D | 11,514 | 5,687 | 17,593 | |
| 2008 | D | 12,524 | 6,133 | 19,129 | |
| 2004 | D | 11,069 | 7,616 | 19,065 | |
| 2000 | D | 9,021 | 7,284 | 17,677 | |
| 1996 | D | 8,139 | 5,229 | 16,152 | |
| 1992 | D | 8,178 | 5,895 | 18,216 | |
| 1988 | R | 7,174 | 8,387 | 15,725 | |
| 1984 | R | 6,039 | 9,035 | 15,284 | |
| 1980 | R | 5,361 | 6,091 | 13,721 | |
| 1976 | R | 5,443 | 6,712 | 12,387 | |
| 1972 | R | 4,804 | 7,542 | 12,453 | |
| 1968 | R | 4,966 | 5,967 | 11,416 | |
| 1964 | D | 7,359 | 3,895 | 11,254 | |
| 1960 | R | 4,502 | 7,099 | 11,602 | |
| 1956 | R | 2,719 | 8,434 | 11,157 | |
| 1952 | R | 3,018 | 8,385 | 11,437 | |
| 1948 | R | 3,340 | 5,840 | 9,374 | |
| 1944 | R | 3,709 | 5,252 | 8,961 | |
| 1940 | R | 4,308 | 5,845 | 10,180 | |
| 1936 | R | 4,166 | 5,515 | 9,834 | |
| 1932 | R | 3,964 | 5,250 | 9,416 | |
| 1928 | R | 3,498 | 6,114 | 9,630 | |
| 1924 | R | 1,466 | 5,341 | 7,325 | |
| 1920 | R | 1,615 | 4,172 | 5,841 | |
| 1916 | R | 1,590 | 2,602 | 4,308 | |
| 1912 | R | 1,057 | 1,464 | 4,055 | |
| 1908 | R | 748 | 2,453 | 3,330 | |
| 1904 | R | 745 | 2,419 | 3,256 | |
| 1900 | R | 871 | 2,666 | 3,575 | |
| 1896 | R | 656 | 3,086 | 3,839 | |
| 1892 | R | 1,155 | 2,196 | 3,420 | |
| 1888 | — | — | — | — | |
| 1884 | — | — | — | — | |
| 1880 | — | — | — | — | |
| 1876 | — | — | — | — |
Despite its small-town and agricultural character, Bennington County has delivered consistent Democratic presidential margins above 20 points, reflecting a broader leftward shift across Vermont's once-competitive southern counties.
The Democratic margin in Bennington County reached its widest at thirty-three points in 2008. The margin in 2024 was twenty points — still decisive.
Bennington County's loyalty is rooted in its place. Median household income of $73,325, a 92% non-Hispanic-white share, and a population of 37,269 together describe a community whose political habits are deeply settled. The county's voting pattern over the last decade is most similar to that of Lamoille County and Windsor County.
