Cultural Resources include: Choptank River village, landing, grist mills, tanneries, blacksmith shops, wheelwright shops, canneries, pudding factory, a plow factory and a large open market house was built ca. 1830.
Denton is significant historically for its role as the seat of Caroline County and as a regional market center along Maryland's Eastern Shore from the early-19th century through the mid-1930's. Centrally located in Caroline County and situated on the Choptank River, Denton is strategically located. Represented by a wealth of commercial, residential, public, and religious architecture in a variety of periods, styles and forms, the Denton Historic District is also architecturally significant. Apart from a few clusters of modern development near Market Street at Second and Fifth Streets, the district exhibits a strong sense of historic integrity and continuity.
A small village had been established on the site of present-day Denton by 1781. The waterfront portions of this site was originally called Pig Point and served mainly as a landing (see Pig Point Landings). The site had been selected as county seat for Caroline County by an act of the Maryland Assembly in 1774. However the first courthouse, said to be a replica of Independence Hall, was not built until 1797 (some accounts say 1791) and razed in 1895. The courthouse square became and remains the focal point of the town. The county seat changed its name from Pig Point to Eden-Town, shortened to Edenton and finally the "E" dropped and it was called Denton by 1791.
Throughout much of its history Denton's economy has been based on the surrounding agrarian activities. A number of small industries developed in the late 18th and early 19th centuries to serve the needs of the farmers including gristmills, tanneries, blacksmith shops, wheelwright shops, and a plow factory. The General Assembly authorized a wharf (and connecting causeway through the marsh) in November 1792. A ferry originally operated across the river (see Denton Ferry). A bridge was constructed in 1811 or soon after (see Denton Bridge). A large open market house was built ca. 1830 on the southeast corner of the courthouse square where farmers could display and sell their livestock, poultry and produce. In 1807 Solomon Brown operated "currying and tanner's shops" along the river at the intersection of 2nd and Dry (now Lincoln) Street. In the same year John Dawson and A. Ross each operated a "granary" along Front Street and the river. Steamboat service to Denton (West Denton) began in 1842 and ran at least until the 1920's.
The Town of Denton and, in fact, the entire Eastern Shore of Maryland were somewhat isolated during the early 19th century, but several developments occurred starting mid-century which led to increased communication and prosperity in the region. A stage line began operating ca. 1860 through Denton on its route from Fenton, Delaware, to Easton Maryland. During the Civil War a Union vessel was sent to Denton in an unsuccessful attempt to round-up Southern sympathizers. Following the Civil War, Denton's location about fifty miles up the Choptank River from the Chesapeake Bay enabled it to become an important shipping point for agricultural products. Steamboat traffic on the Chesapeake increased dramatically during the latter half of the 19th century, and Denton, like other Eastern Shore towns such as Chestertown, Easton, and Cambridge, became a regular port-of-call for Baltimore based steamer lines. The Queen Anne Railroad Company constructed a line from Love Point to Denton. Construction of the railroad had less impact on the town's economy because it served only as a connecting line to a Baltimore steamer and did not provide a direct connection to northern cities.
Changes in transportation and the local economy generated changes in the physical aspects of the town. In 1875 the second iron bridge replaced the ca. 1813 bridge which crossed the Choptank River just west of the town. Gaps in the blocks east of Fifth Street were filled in with new construction and the earlier structures were removed or remodeled. The commercial district along Market Street between Second and Third Streets was rebuilt following a disastrous fire on those blocks in 1865. The first substantial church building was constructed on Market Street in 1867. The local Methodist Episcopal congregation that had organized by 1816 constructed this brick Romanesque style structure. The Protestant Episcopal Church congregation, which formed in 1870, built a small Victorian Gothic style church on the courthouse square in 1873-74. The town's third church, the Methodist Protestant Church, was erected on Market Street in 1897. A Gothic Revival schoolhouse was constructed on South Second Street in 1883. The county's first financial institution was organized as the Denton National Bank in 1881. The first National Bank building was constructed ca. 1885 at the corner of Market Street and Fourth Street. The Romanesque styling of this brick building was echoed in the design of the new courthouse, built in 1895. Many Victorian residences of various sizes and degrees of architectural refinement were constructed during this time period as well.
The early 20th century was both a boom period and a transition period in Denton. The lumber and food canning industries gained importance. Shipping of farm products remained important, but overland transport by truck gradually replaced the river steamers and trains. Public improvements included construction of the first county high school in 1901, construction of a gasworks in 1901 and waterworks in 1902, construction of a concrete bridge over the Choptank River in 1913, and paving Market Street with concrete in 1915-1916.
Several canneries were built in Denton including: G. T. Redden (1889-1934) who operated a cannery on Greensboro Road about one and half miles northeast of Denton, Charles M. Parker (1901), Katie N. Hardcastle (1910-1934) who operated a cannery and produced mincemeat on Lincoln Street; Denton Canning Company (1903); Burton W. Parker (1910-1920); Denton Cannery (1923); Raughley, Alfred & Company (1924-1925); Fred B. Nuttle (1934-1940); and Denton Canning Company (1946-1957). John and Jim Hardcastle operated a plum factory (no date). 55 Some of these canneries may have actually been located in West Denton where at least five additional canneries also operated (see West Denton).
Fishing for carp (Cyprinus carpio), herring (Family Clupeidae), shad (Family Clupeidae) and rock (striped bass) (Morone saxatilis) was carried out at fishing shores near Denton called "Short Wretch," "Middle Wretch" and "The Hornes" also called "Deep Water" (also see Denton Wharves).
Notable commercial development occurred along the west end of Market Street during the first decade of the 20th century. The Law Building was constructed in 1902 with offices, retail space and the Post Office on the first floor, law offices on the second floor, and lodge rooms and a law library on the third floor. People's National Bank with its unique stone facade was built on the adjacent lot ca. 1906. The First National Bank moved to its new building at the corner of Market and Second Streets in 1902. Also constructed on Market Street were the Denton Journal Building in 1901 and the Carter Building in 1905. As the century progressed other brick and concrete block commercial buildings were added to the Market Street business district.
Residential development and the construction of the two churches accompanied the substantial growth of Denton's population during the period 1900-1925. The town expanded eastward as construction of gable-front houses, bungalows and cubical cottages progressed. Several of earlier Victorian structures were altered according to the architectural fashions of the time. Common alterations included covering the exterior with wood shingles to convey a rustic appearance and changing the porch details from Victorian to classical. Perhaps most expressive of the prosperity of this period are the large Colonial Revival and Shingle style residences built along Fifth Avenue, the town's most elegant neighborhood.
The early 20th century growth period ended with the Depression of the 1930's and the appearance of the district has chanced little since that time. A fire in the mid-1930's destroyed a small part of the business district, but this was rebuilt with two-story brick structure similar to the existing buildings. Since 1960 several Colonial Revival buildings including two banks, the county library and the courthouse additions have been constructed in the district. Other modern construction has been minimal. Adaptive use of several historic buildings such as the old People's National Bank building, now used as a law office, and the old Caroline County High School, currently used as a day-care center, has been an effective preservation method. The Women's Club of Denton has shown an active interest in preservation. This organization owns the Denton Schoolhouse on South Second Street that has been listed in the National Register since 1978.