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The first European settlers began moving into Brentwood in the end of the 18th century, during an era when Native Americans from Alabama and Georgia used the area for hunting, which caused a lot of friction, including the famous massacre at the Southerland Mayfield family fort in 1786. During that attack, three men were killed, including Mayfield, and his son was taken and held captive for a decade. Many of the original settlers had been given land grants for their service in the American Revolution. During the American Civil War, in March of 1863, the Confederate Army marched into the Union town with the objective of capturing the railroad. Confederate Brigadier General led a column of men into town after cutting the telegraph wires and isolating Union Lt. Colonel Bloodgood. Brentwood was destroyed in the battle that ensued. The Confederates suffered between 3 and 59 casualties and the Federals suffered between 500 and 800. Bloodgood surrendered that day, and was later court-martialed for cowardice.

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