The non-residential historic structures include four specialty shops, a former theater, four churches, the Town Hall, two former schools, three warehouses and an inn.

The present-day Middletown area began developing in the mid-18th century due to the Great Wagon Road that brought settlers and commerce to the Shenandoah Valley.

When the Virginia General Assembly formally established Middletown in 1796, there were already many residential and commercial buildings in the area.

In the 20th century Route 11 was widened, utilities were installed, and the county's first high school opened in Middletown.

Due to the efforts of a local heritage group and with support from residents, a large portion of the town was listed as a historic district by the VLR and NRHP in 2003.

Town officials are hoping to avoid further demolition by encouraging residents to maintain their property and by preventing the construction of buildings that do not fit in with the character of the historic district.

The town is bordered by Laurel Ridge Community College to the north, Interstate 81 to the east, and the Cedar Creek and Belle Grove National Historical Park to the south.

The historic district is centered around Main Street, the portion of U.S. Route 11 located in the town, which runs southwest to northeast.

The Van Meter brothers, who had acquired a 40,000-acre (16,187 ha) portion of this grant, later conveyed the land to German immigrant Jost Hite in 1731.

During the next few decades, a 2,168-acre (877 ha) portion of this grant was conveyed to various men, ending with Dr. Peter Senseney, who acquired it in several transactions beginning in 1776.

Middletown, possibly named because it was halfway between Newtown (later renamed Stephens City) and Strasburg, was established on May 4, 1796, by the Virginia General Assembly.

During his stewardship local churches were founded, businesses continued to open, and two schools operated, all while the population slowly increased.

The Colored People's Church congregation later moved to nearby 7913 Senseney Avenue which was named Mt.

[2][5] The white Methodist congregation built a brick church in 1852 on the corner of Main and present-day Third Streets, which has since been demolished.

Soldiers traveled up and down the turnpike between Winchester and points south, with several bloody battles taking place in and around Middletown.

Fighting took place around the Belle Grove Plantation and Monte Vista before moving north through the town.

[2][3][4] Middletown slowly recovered after the war, with commerce increasing after a railroad track was built around 1870 between Winchester and Strasburg.

[2][4][7] Electricity and phone service arrived in Middletown in the early 20th century, and when Route 11 was widened, none of the properties fronting Main Street were demolished because buildings had been constructed further away from the road in anticipation of future development.

[2][4] The town's first auto repair shop, Stubley's Garage (no address listed; between 7957 and 7969 Main Street) was built around this time.

African American children attended the segregated Senseney-Middletown Colored Elementary School (7883 Senseney Avenue).

One of the requirements in the deed was that the Independent Order of Odd Fellows (IOOF) would be allowed to met on the second floor.

Among the buildings constructed in the 1930s and 1940s were a dance hall and eleven bungalows for employees of the American Viscose Corporation in nearby Front Royal.

In 1946 the Bordon-Lee Theater (7853 Main Street), which played films, was built on the site of the former Shenandoah Normal School, which had been recently destroyed in a fire.

Fifteen years later the Bordon-Lee building began housing a live theater company and was later renamed the Wayside Theatre.

[2][7] A water tower was built on Church Street in 1950 followed by the installation of natural gas mains in the late 1950s.

[11] In the 2020s a proposed historic overlay district that would encompass 176 parcels in the town was met with opposition from some residents, who feared it would lead to property maintenance guidelines and reviews of any architectural changes to buildings.

[12] Town officials aim to establish an ordinance to preserve the historic district's remaining contributing buildings.

A large number of outbuildings are among the contributing properties, including barns, icehouses, chicken coops, and outhouses.

The most notable of these is the Wayside Inn (7783 Main Street), the oldest portion of which dates back to 1797 and features Colonial Revival details.

The vernacular Jacob Rodes House (7828 Main Street), featuring Greek Revival details, was also built around 1800.