Originally 88 acres (360,000 m2) were sold to Henry Funk by Frederick Calvert, 6th Baron Baltimore in 1754 and settled as Jerusalem.

A strong Confederate presence at Funkstown threatened any Union advance against Gen. Robert E. Lee's position near Williamsport and the Potomac River as he retreated to Virginia after the Battle of Gettysburg.

Stuart's cavalry, posted at Funkstown, posed a serious risk to the Federal right and rear if the Union army lunged west from Boonsboro.

Stuart, meanwhile, determined to wage a spirited defense to ensure Lee time to complete fortifications protecting his army and his avenue of retreat.

Gen. John Buford's Federal cavalry division cautiously approached Funkstown via the National Road on Friday morning July 10, 1863, it encountered Stuart's crescent-shaped, three-mile-long battle line.

A nearby stone barn and barnyard wall proved a superb defensive position for the 34th Virginia Battalion's dismounted cavalry.

Col. Thomas C. Devin's dismounted Union cavalry brigade attacked about 8:00 a.m. By mid-afternoon, with Buford's cavalrymen running low on ammunition and gaining little ground, Col. Lewis A.

Unbeknownst to the Vermonters, Gen. George T. Anderson's Confederate brigade now faced them, the first time opposing infantry had clashed since the Battle of Gettysburg.

According to the United States Census Bureau, the town has a total area of 0.36 square miles (0.93 km2), all land.