Brooksville, established in 1856 by the merger of the towns of Melendez and Pierceville, took its name to honor Preston Brooks, a pro-slavery congressman from South Carolina, who caned and seriously injured Charles Sumner, an abolitionist and United States senator from Massachusetts.

Fort DeSoto, established in 1840 to give protection to settlers from Native Americans, was located at the northeastern edge of present-day Brooksville on Croom Road about one-half mile east of U.S. Highway 41.

The fort was also a trading post and a regular stop on the Concord stagecoach line which ran from Palatka to Tampa.

[citation needed] On September 12, 1842, Seminole Indians attacked the McDaniel party which was riding near the settlement known as "Chocochatti" or "Chocachatti", south of Brooksville, killing Mrs. Charlotte Crum (née Winn/Wynn; 1792–1842).

In the early 1840s the population shifted about 3 miles (5 km) to the south, where a settlement formed by the Hope and Saxon families became known as Pierceville.

[citation needed] A study of lynchings recorded in Hernando County in the late 19th and early 20th centuries revealed it had one of the highest per capita rates of violence against blacks in the United States.

After the murder, the investigation was stymied by local actions to prevent bringing to justice the white men accused in his killing.

[11] The 1920s saw a resurgence of Ku Klux Klan activity and lynchings; as a result, many black residents left the area.

The school board paid teachers with chits, and Weeks Hardware "accepted chickens and sides of bacon" as payment.

[15] An example of racism in the city was the creation of the "Lewis Plantation and Turpentine Still", which claimed to show life in African-American rural communities, but contained black residents dressing and acting in stereotypes to entertain white tourists.

The business section includes eleven shopping centers, and Brooksville–Tampa Bay Regional Airport is 6 miles (10 km) south of the city.

[citation needed] Jerome Brown, defensive tackle for the Philadelphia Eagles was a graduate of Brooksville's Hernando High School.

[18] A minor controversy arose in the summer of 2010 when local media and residents brought attention to the origin of the town's name, calling it "shameful".

However, the city's official website did remove a page which discussed the Brooks/Sumner encounter and had cast Brooks in a positive light.

[citation needed] The first annual "Get Healthy Brooksville Cycling Classic" was held in 2010 and attracted cyclists from all over the state.