Middletown Covered Bridge
South Mountain Creamery
Catoctin Creek Bridge

Local histories report that the western end of Middletown was settled first with proximity to the source of water, Catoctin Creek, and the naturally occurring flatter lands. From Boileau Court, you can look across toward Tanner’s Creek which derived its name from the several leather tanning facilities built along the creek and West Main Street in the early 19th century. Tanner’s Branch still runs from an underground spring near Main’s Alley, behind the buildings on the south side of Main Street, and down to Catoctin Creek. South Mountain Creamery was located at the extreme western edge of Middletown on land later developed as Creamery Row in the 500 block of West Main Street. Many structures in this area are built close together, nestled into the hills on the north side of the road. Look for the vernacular Germanic building traditions of the mid 1800s-front façades with a window-window-door arrangement, and ground-floor entries to the basement instead of the main living quarters.

Catoction Creek Bridge (c. 1850, 1920)

Just before the 1862 Battle of South Mountain, confederate soldiers led by Confederate Lieutenant General Jubal Early burned it down. After the war, it was rebuilt on stone abutments. In the 1920s, as part of the federally funded Good Roads Program, the covered bridge was replaced with a concrete arch bridge.

Middletown Covered Bridge (c. 1809, 1868)

According to the Baltimore Sun paper on October 17, 1937: “There is only one covered bridge that can be definitely dated; it stands near Middletown, Frederick County, and was put up in 1809.” This bridge is considered by some historians to be the first covered bridge constructed in Maryland located approximately 0.6 miles southwest of the National Road, on Bidle Road. Unfortunately, the bridge
is no longer standing.

504 West Main Street (c. 1850)

Known as the Jacob Rudy House, was where future president Lt. Col. Rutherford B. Hayes received care after being wounded at the Battle of South Mountain. Lucy Hayes soon arrived to care for her husband; and she later volunteered as a nurse.

10 Walnut Street (1929)

The original Schlosser Tannery stood on this site until 1915, when Calvin and Lola Gladhill relocated their furniture business from Myersville to Middletown. Gladhill’s sold a variety of goods: furniture, wagons, buggies, and carriages, as well as funeral related services and caskets. The original structure was razed in 1929, replaced by the present structure housing their furniture showrooms and workshops. One of the town’s oldest continuously operating businesses, Gladhill Furniture celebrated their 100th anniversary in 2015.

14 Walnut Street (c. 1900)

The Gladhills lived in the house directly west of the store on Walnut Street. This two-story, three-bay house with a central, cross-axis gable features sidelights and transoms surrounding the front door-all typical of houses built in town in the mid-19th century. Note the early-20th century cast-concrete porch columns designed in a modified Corinthian style. They are mounted on rusticated castconcrete block plinths, first used in Middletown at Gray Haven, 709 East Main Street.

16 Walnut Street (c. 1840)

The town’s oldest known dwelling is the original log section of the Smithfield House, built around 1730 by gunsmith Frederick Lauber. According to a report dated March 1, 1863, by Dr. Jonathan Letterman, “At Middletown, ten buildings were occupied for hospital purposes, from the day of the battle of South Mountain.”

210 West Main Street (c. 1860)

This two-story, four-bay house once belonged to tanner John Appleman. It was probably constructed of logs, though today it is sheathed in vinyl siding and sits on a raised stone foundation with a front porch supported by Doric columns. After the Battle of South Mountain, a wounded soldier made his way to Middletown, where his wife had family. He stopped at this house and learned that the Applemans were related to his company lieutenant.

308 West Main Street (c. 1850)

This large house was associated with the Schlosser Tannery. The tannery was a large complex with numerous brick buildings. In addition to its historic association with the tannery, the entrance with sidelights and transom is one of the best examples of the Greek Revival style in Middletown.