Sheriff Stephen Wiley Brewer Farmstead

Pittsboro is a town in Chatham County, North Carolina, United States. The population was 3,743 at the 2010 census and 4,537 at the 2020 census. It is the county seat of Chatham County.The town was established in the late 18th century, shortly after the American Revolution, as the county seat for the newly formed Chatham County. In the years leading up to the American Civil War, the economy was dominated by small-scale farms that relied heavily on enslaved labor, and in the aftermath of the civil war, racial tensions were high, and the town was noted for a number of lynchings and other racial violence in the late 19th century. Industrialization came to the community in the late 19th century, as a number of rivers cross the area providing locations for mills and factories. Economic and population growth would continue into and throughout the 20th century. As industry moved away from the community, it has in the 21st century transitioned into a bedroom community for the nearby cities of the Research Triangle region.

McClenahan House is a historic home located at Pittsboro, Chatham County, North Carolina. It was built before 1830, and is a one-story, three-bay, frame dwelling on a brick foundation with Greek Revival and Federal style design elements. The house began as a one-room house and is one of only four buildings in Pittsboro that dates from the settlement era.It was listed on the National Register of Historic Places in 1982. It is located in the Pittsboro Historic District.

Patrick St. Lawrence House, also known as the Yellow House, is a historic home located at Pittsboro, Chatham County, North Carolina. It was built about 1790, and is a two-story, center hall Georgian style architecture frame dwelling with a low gable roof. It was originally built as an inn and overlooked the courthouse square. It is Pittsboro's oldest building. It has been moved three times and is now located on S. Small St. It was listed on the National Register of Historic Places in 1982. It is located in the Pittsboro Historic District.

Moore-Manning House is a historic home located at Pittsboro, Chatham County, North Carolina. It was built in the 1830s, and is a two-story, three-bay, Federal style frame dwelling with a hipped roof. The house was renovated in 1858 and a two-story wing added.It was listed on the National Register of Historic Places in 1982. It is located in the Pittsboro Historic District.

Pittsboro Historic District is a national historic district located at Pittsboro, Chatham County, North Carolina. The district encompasses 131 contributing buildings, 3 contributing sites, and 1 contributing object in the county seat of Pittsboro. Located in the district and separately listed are the Chatham County Courthouse, the Hall-London House, the Moore-Manning House, the Reid House, the Lewis Freeman House, the McClenahan House, and the Patrick St. Lawrence House. Other notable buildings include the Blair Hotel, Pilkington Drug Store / S & T' s Soda Shoppe, Justice Motor Company building (1949), St. Bartholomew's Episcopal Church (1832), Pittsboro United Methodist Church (c. 1836), and Queen Anne style Henry H. Fike House (c. 1895).It was listed on the National Register of Historic Places in 2000.

Pittsboro Masonic Lodge, also known as Columbus Lodge No. 102, is a historic Masonic Lodge located at Pittsboro, Chatham County, North Carolina. It was built in 1838, and is a two-story, Greek Revival style frame building. In 1846, it was enlarged by the addition of the distinctive pedimented second-story overhang carried on heavy square pillars. It is one of the oldest still-functioning Masonic halls in North Carolina.It was listed on the National Register of Historic Places in 1978.

Hall-London House is a historic home located in Pittsboro, Chatham County, North Carolina. It was built in about 1836, is a tall two-story, five bay Federal / Greek Revival style frame dwelling. It features a broad Gothic Revival style front porch. A two-story rear ell was added about 1900.It was listed on the National Register of Historic Places in 1982. It is located in the Pittsboro Historic District. It has been occupied by Bradshaw & Robinson, LLP, a local law firm, since 2000, and its predecessor law firms going back to 1984.

Pittsboro Presbyterian Church is a historic Presbyterian church located on N. East Street in Pittsboro, Chatham County, North Carolina. It was built about 1850, and is a one-story brick church. The tower and steeple were replaced in 1875 following a tornado, and again in the 1920s and in 1971.It was listed on the National Register of Historic Places in 1978.

The Chatham County Courthouse is a historic courthouse located at Pittsboro, Chatham County, North Carolina. It sits at the center of town in the middle of a traffic circle. It was built in 1881 for $10,666 and is a two-story rectangular brick structure in the Late Victorian style. It features a two-story classical portico crowned with a distinctive three-stage cupola. A one-story addition was built in the 1930s by the Works Progress Administration. In 1959, extensive renovations were performed on the building.It was listed on the National Register of Historic Places in 1979. It is located in the Pittsboro Historic District. A fire on March 24, 2010, did great damage to the building which was in the midst of another renovation. The restored building reopened April 20, 2013 with an exhibit covering Chatham County history on the first floor and a courtroom on the second.In 1907, the county gave a license to the United Daughters of the Confederacy to place a statue of a Confederate soldier outside the courthouse. In 2019, the Chatham County Board of Commissioners voted to rescind this license, and the statue was removed as part of the trend toward removal of Confederate monuments and memorials in the 2010s.

Reid House is a historic home located at Pittsboro, Chatham County, North Carolina. It was built about 1850, and is a 1+1⁄2-story, three-bay, Federal / Greek Revival style double-pile plan frame dwelling. It has a broad gable roof and two interior chimneys. The house was renovated in the 1930s.It was listed on the National Register of Historic Places in 1982. It is located in the Pittsboro Historic District.

Lewis Freeman House is a historic home located at Pittsboro, Chatham County, North Carolina. The original section was built between about 1811 and 1837, and expanded through the 1890s. It is a one-story, three bay frame cottage with Queen Anne style design elements. The original one-room structure represents the modest home of Lewis Freeman, a free black settler in Pittsboro. The home is one of four remaining dwellings from the town's initial settlement. Due to the lack of records during the early 1800s, little is known about the first residents of the area. It was listed on the National Register of Historic Places in 1982. It is located in the Pittsboro Historic District.

Kelvin was a historic home located at Pittsboro, Chatham County, North Carolina. It was built about 1831, was a two-story, five bay Federal style single pile frame dwelling. The house had a gable roof and exterior end chimneys. It had a one-story addition built about 1838. It originally housed a private girls school established by wealthy landowner Colonel Edward Jones Kelvin. It has been demolished. It was listed on the National Register of Historic Places in 1982.