The land was first granted by the Crown to Captain Isaac Pennington in 1734, and George Washington surveyed it on October 23, 1750.

[7] According to legend, Daniel Morgan would engage in combat with young toughs at the intersection, having first piled large stones nearby to use as ammunition in case of need.

[8] Because of this story, and a rowdy tavern nearby, the area was first given the informal name of "Battle Town".

Smith named his estate "Battle Town", and on the site of the former tavern he built a clapboard homestead.

Daniel Morgan returned to the area after distinguishing himself in the Revolution, living at Saratoga, and briefly at Soldier's Rest.

In 1926, Byrd purchased Rosemont, an estate adjacent to his family's apple orchards in Berryville.

Virginia State Route 7 bypasses Berryville along its northern border as a four-lane freeway, leading west to Winchester and east across the Blue Ridge Mountains 24 miles (39 km) to Leesburg.

According to the United States Census Bureau, Berryville has a total area of 2.3 square miles (5.9 km2), all of it land.

SR 7 bypasses the town just to the north, extending west to Winchester and east to Leesburg.

The climate in this area is characterized by hot, humid summers and generally mild to cool winters.

[14] In addition to Soldier's Rest, the Berryville Historic District, Chapel Hill, Clermont, Cool Spring Battlefield, Fairfield, Glendale Farm, Josephine City School, Long Marsh Run Rural Historic District, Norwood, Old Clarke County Courthouse, Smithfield Farm, and Wickliffe Church are listed on the National Register of Historic Places.