| Year | Won | Margin | Democratic | Republican | Total |
|---|---|---|---|---|---|
| 2024 | R | 4,860 | 11,053 | 16,330 | |
| 2020 | R | 5,095 | 10,286 | 15,797 | |
| 2016 | R | 4,009 | 9,368 | 13,951 | |
| 2012 | R | 4,970 | 8,098 | 13,357 | |
| 2008 | R | 4,971 | 8,015 | 13,218 | |
| 2004 | R | 3,810 | 7,396 | 11,356 | |
| 2000 | R | 3,396 | 5,300 | 8,952 | |
| 1996 | R | 3,251 | 3,874 | 8,177 | |
| 1992 | R | 2,822 | 3,856 | 8,459 | |
| 1988 | R | 2,440 | 4,661 | 7,123 | |
| 1984 | R | 2,198 | 4,876 | 7,099 | |
| 1980 | R | 2,833 | 3,582 | 6,765 | |
| 1976 | R | 3,017 | 3,114 | 6,131 | |
| 1972 | R | 1,567 | 4,325 | 5,948 | |
| 1968 | R | 1,697 | 3,120 | 6,231 | |
| 1964 | D | 3,710 | 2,696 | 6,406 | |
| 1960 | R | 3,381 | 3,698 | 7,079 | |
| 1956 | R | 2,702 | 4,208 | 6,910 | |
| 1952 | R | 2,733 | 4,155 | 6,899 | |
| 1948 | R | 2,430 | 2,746 | 5,208 | |
| 1944 | R | 2,060 | 3,073 | 5,133 | |
| 1940 | D | 3,284 | 3,087 | 6,401 | |
| 1936 | D | 3,579 | 2,611 | 6,206 | |
| 1932 | D | 3,651 | 1,998 | 5,671 | |
| 1928 | R | 2,030 | 3,270 | 5,322 | |
| 1924 | D | 2,493 | 2,210 | 4,888 | |
| 1920 | D | 3,012 | 2,929 | 5,990 | |
| 1916 | D | 1,965 | 1,666 | 3,712 | |
| 1912 | D | 3,659 | 1,445 | 3,645 | |
| 1908 | D | 3,370 | 1,945 | 130 | |
| 1904 | D | 3,721 | 1,452 | 109 | |
| 1900 | R | 1,774 | 1,796 | 12 | |
| 1896 | R | 1,651 | 1,686 | 3,480 | |
| 1892 | D | 1,453 | 1,344 | 2,946 | |
| 1888 | — | — | — | — | |
| 1884 | — | — | — | — | |
| 1880 | — | — | — | — | |
| 1876 | — | — | — | — |
Tucked into Maryland's Eastern Shore, Caroline County delivers presidential margins rarely seen in a state that trends heavily Democratic statewide — the 2024 gap exceeded 37 points, reflecting a rural, working-class electorate sharply out of step with the Baltimore-Washington corridor.
The Democratic margin in Caroline County peaked at 100 points in 1904. By 1968 the county had flipped, voting Republican for the first time in many years. The 2024 margin was thirty-eight points, the most Republican-leaning result in the county's modern history.
The economic context is the key. Caroline County's median household income of $68,457 sits well below state and national norms, and 12% of residents live below the federal poverty line. The shift here is part of a broader realignment of working-class places across the country. The county's voting pattern over the last decade is most similar to that of Clinton County and Miami County.