The area from roughly Walnut Street to Church street is the heart of Middletown. In 1768, a year after the town’s founding, Michael Jesserong laid out 28 lots on the 44-acre plot of land called Smithfield, subsequently selling the plots as being in the town of Middletown to Conrac Crone. Thus, Jesserong is credited with being the town’s founder and Crone is the first developer.
This stone house, headquarters of the Middletown ValleyHistorical Society, is a two-story, three-bay, sandstone house with a slate shingle roof. The full-width front porch was a 20th-century addition. At the rear of the house is a detached summer kitchen.
This two-story wood sided house with Italianate features has an original storefront with a bracketed cornice on the first floor, dating from its use as a millinery. The hipped roof has overhanging eaves with brackets, and the east side has a small cross gable with a fanlight window.
This three-story, five-bay, gable-front brick building was originally the Methodist Episcopal Church. Original Greek Revival elements include a three-part window converted to a door on the third story, a round window in the gable peak, and brick pilasters topped with a capital on the front.
This three-story, three-bay Italianate brick structure also features a dominant bracketed cornice and stone foundation. The Catoctin Whig was published here as early as 1858 by George C. Rhoderick, and was issued continuously throughout the Civil War. The current building housed the printing of the Valley Register until 1984, when the Rhoderick family sold the business. Lamar Sanitarium housed one of the first modern surgical suites in Frederick County, located at 200 West Main Street. The Valley Register, originally the Catoctin Whig, was published at 123 West Main Street from approximately 1858 to 1991.
Today, we take soaring high-rises and church steeples for granted. In 1859, when Zion Lutheran Church was completed, its steeple dwarfed the surrounding buildings and was visible throughout the Valley. The building is brick with a standing-seam metal roof. Greek Revival details include the large pediment on the front façade, with a wide frieze band and dental molding at the cornice—all supported by four Ionic columns. The steeple clock, made by Seth Thomas, was installed in 1909.
One of the most photographed buildings in Middletown, this small, gable-front building with pressed-metal shingles captures attention with its Gothic Revival scroll-cut trim and finial at the gable peak. It was originally a harness shop, with a livery stable on the rear side of the lot facing West Green Street. Later a tailoring shop, jewelry store, millinery shop, and now a barber shop. The buildings from 2–14 West Main Street are the most historically intact row of commercial buildings along West Main Street.
This two story, three-bay, Greek Revival brick house was built as a parsonage by the Lutheran Church and the wraparound porch was added at the end of the 19th Century. The nearby Lutheran Lecture Hall and a small pastor’s study were removed when the porch was added.
The Arnett building, a two-story, five-bay brick building, has a metal roof, heavy bracketed cornice, and a brick parapet with glazed terra cotta coping rising around the cornice and surrounding the roofline. This is a good example of an early-20th century mixed-use building.
In 1919, the Middletown Defense League and a group appointed by Md. Governor Emerson Harrington planned to build a memorial honoring World War I veterans. The building was designed by Edward Leber from York, PA, and built by Roy Poole. In 1923 the Memorial Hall theater and community center opened and became the heart of town life. The building has been home to the American Legion Post, Middletown Fire Company, and local library.
The two-story, five-bay house may have been originally built of logs, and is now covered in stucco on the north and east. It features two storefronts with plate glass and central recessed entrances. This was the home of the Doub family and later the Coblentz family, who rented out as Long’s Electrical Shop, Warren’s Men’s Shop, and Harry Holter’s Barber Shop.
This two-story, three-bay house, with its distinctive Flemish bond brick pattern, has housed many tenants over the years, including Mr. and Mrs. Adam Lorentz who operated a candy store here c. 1900.
This was a residence of Charles F. Main, proprietor of Main’s Meat Market and later Main’s Quality Ice Cream.
A blacksmith shop once operated in the west side of the original log building, with the Coblentz and Cook Meat Market in the east side. The blacksmith shop was converted to a confectionary in 1889. In 1922, Charles F. Main started an ice cream shop and factory here. Main’s Quality Ice Cream drew generations of Marylanders until it closed in 1969. Since 2007 it has been The Main Cup restaurant.
Queen Anne building #20 (1888) was constructed for the Valley Savings Bank—note the letters “VSB” set in red slate in the tower roof. It was the bank until 1923, then became a US Post Office until the late 1960s. Today it is a private residence, with its front façade virtually unchanged since construction. Building #24 (1923) makes a grand statement with its soaring entrance dominated by the large Classical Revival fluted Doric columns, entablature, and central pediment. It is now Middletown Valley Bank.
The Stonebraker and Harbaugh-Shafer building, commonly known as “Rudy’s Hall,” is one of Middletown’s most significant buildings. The brick Federal-style house and store was built by Samuel Harbaugh and later purchased by prosperous farmer Peter Shafer in 1858. The second floor served as a hospital following nearby Civil War battles. In July 1864, Shafer provided the ransom money to Confederate Gen. Jubal Early to spare the town from being burned. The building was used as shop and storage area until the late 1890s. After Shafer’s death, William Rudy bought the building. “Rudy’s Hall” on the second floor hosted stage productions and community events. It served as the town hall, with the lower level as a post office and library.
A small brick house and outbuildings were already standing on this property when in 1841 for use by James Stevens as a tavern and stable. According to the Catoctin Whig, October 1844, it provided “hostlers, good stablins, and Bar and Table.” In 1906, Dr. Lewis Lamar purchased the property and remodeled the building for use as his residence, examination office, state-of-the-art surgical suite, recovery rooms, and outdoor rest area for patients. The operating room had floor-to-ceiling glazed tiles, a skylight, built-in sinks, and floor drains. A gas plant in the basement provided lighting. Architecturally, the Lamar House echoes the large Victorian houses farther east on Main Street. A porte cochere extends over the sidewalk, supported by Corinthian columns with a balustrade railing and jerkin-head dormers on either side of a central tower.