The town of Boonsboro was founded by brothers George and William Boone, relatives of the more famous Daniel Boone. It is situated along the main road leading from Hagerstown to Fredrick, with the original land records referring to the area as ‘Boones Berry.’ The town itself was laid out by the brother’s in half-acre lots in 1792 and was later incorporated in 1831.

The town was originally named Margaretsville in honor of George's wife, but was eventually changed to Boonesborough, and then later to its shortened spelling – Boonsboro. With the construction of the National Road, a turnpike connecting Baltimore to the west, Boonsboro grew and prospered. In 1823, a new process called "macadam" was used to finish an unpaved section of the turnpike from Boonsboro to Hagerstown. This was the first time the road building process was used in the United States.

On the 4th of July in 1827, the citizens of Boonsboro erected the first monument to honor George Washington on top of South Mountain. Used during the Civil War, the monument was restored in 1882 and again in 1936 by the Civilian Conservation Corps. The first battle of the Civil War fought on northern soil was the Battle of South Mountain September 14, 1862. Churches, public buildings and homes in the town were used as hospitals.

Today, Boonsboro is a quiet bedroom community catching the over-flow growth of Fredrick County, as commuters to the Baltimore-Washington D.C. area move westward in search of homes or a weekend getaway to a bed and breakfast.