Middletown is located near the junction of I-66 and I-81 in the northern portion Shenandoah Valley, in Frederick County, Virginia, United States. The population was 1,265 at the 2010 census, up from 1,015 at the 2000 census.
Middletown was chartered on May 4, 1796. Some of the first documentation of early Middletown dates back to the late 18th century and is attributed to Dr. Peter Senseney and his wife Magdelen, two German settlers who had migrated from Pennsylvania. The town was originally known as "Senseney Town", a piece of land within the 17th Century Fairfax Grant and gifted to the allies for siding with England during the civil war in the 1600s.
Belle Grove Plantation, about a mile southwest of Middletown, was first settled in about 1750, and its historic Federal-style manor house was completed in 1797. Middletown was the site of numerous military operations in the American Civil War including the Battle of Cedar Creek, fought just south of the town. The area where this battle occurred has been protected as part of the Cedar Creek and Belle Grove National Historical Park. Because the town was founded long before the Civil War, its antebellum history is extensive, as evidenced by the fact that Middletown's Wayside Inn purports to be the longest continuously running inn in America. Wayside Theatre, also located in Middletown, was one of Virginia's oldest professional live theaters (opened 1961, closed 2013).