| Year | Won | Margin | Democratic | Republican | Total |
|---|---|---|---|---|---|
| 2024 | D | 24,579 | 20,083 | 45,389 | |
| 2020 | D | 25,522 | 17,898 | 44,370 | |
| 2016 | D | 22,064 | 16,876 | 41,895 | |
| 2012 | D | 25,380 | 15,156 | 41,360 | |
| 2008 | D | 26,971 | 15,205 | 42,601 | |
| 2004 | D | 24,438 | 16,463 | 41,347 | |
| 2000 | D | 17,382 | 13,793 | 33,395 | |
| 1996 | D | 16,159 | 10,252 | 29,701 | |
| 1992 | D | 15,037 | 11,037 | 32,457 | |
| 1988 | R | 12,339 | 15,002 | 27,512 | |
| 1984 | R | 8,990 | 15,851 | 24,941 | |
| 1980 | R | 7,835 | 13,242 | 25,467 | |
| 1976 | R | 10,388 | 12,554 | 23,305 | |
| 1972 | R | 9,157 | 13,390 | 22,703 | |
| 1968 | R | 9,135 | 10,702 | 20,332 | |
| 1964 | D | 13,626 | 5,958 | 19,584 | |
| 1960 | R | 8,668 | 11,594 | 20,262 | |
| 1956 | R | 5,574 | 12,585 | 18,170 | |
| 1952 | R | 6,710 | 11,897 | 18,607 | |
| 1948 | R | 6,337 | 9,043 | 15,506 | |
| 1944 | R | 7,098 | 8,334 | 15,434 | |
| 1940 | R | 6,916 | 8,302 | 15,218 | |
| 1936 | R | 6,322 | 8,052 | 14,574 | |
| 1932 | R | 5,662 | 7,904 | 13,692 | |
| 1928 | R | 5,025 | 8,673 | 13,756 | |
| 1924 | R | 2,720 | 7,008 | 10,156 | |
| 1920 | R | 3,374 | 6,644 | 10,092 | |
| 1916 | R | 2,779 | 3,337 | 6,244 | |
| 1912 | R | 2,114 | 2,765 | 6,321 | |
| 1908 | R | 1,917 | 4,160 | 6,426 | |
| 1904 | R | 2,002 | 4,364 | 6,550 | |
| 1900 | R | 2,120 | 4,435 | 6,646 | |
| 1896 | R | 1,272 | 4,818 | 6,373 | |
| 1892 | R | 2,994 | 4,024 | 7,142 | |
| 1888 | — | — | — | — | |
| 1884 | — | — | — | — | |
| 1880 | — | — | — | — | |
| 1876 | — | — | — | — |
Cheshire County's margins have tilted Democratic in recent presidential cycles, driven in part by Keene's student and professional population. Its rural hill towns remain more competitive, keeping the county's overall swing potential above zero.
The Democratic margin in Cheshire County reached its widest at thirty-nine points in 1964. The margin in 2024 was ten points — still decisive.
Cheshire County's loyalty is rooted in its place. Median household income of $83,329, a 92% non-Hispanic-white share, and a population of 77,297 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 Strafford County and Bennington County.
