Holden–Roberts Farm

Jacob Jackson Farm, also known as Maple Hill, is a historic home and farm and national historic district located near Hillsborough, Orange County, North Carolina. The Maple Hill dwelling consists of a single pen, hewn log cabin (c. 1810) joined in 1940 by an ell to a two-story, weatherboarded log Federal farmhouse (c. 1820), and a 1 1/2-story, mid-19th century Greek Revival style wing. A frame dining room/kitchen block was added to the cabin in 1946. Also on the property are the contributing barn (c. 1855-1910) and agricultural landscape.It was listed on the National Register of Historic Places in 1994.

St. Mary's Chapel is a historic Episcopal chapel located near Hillsborough, Orange County, North Carolina. The congregation was established in 1759 by Anglicans, and united with the Episcopal Church of North Carolina in 1819. The Gothic Revival style brick church building was constructed in 1858-59 and the adjacent cemetery contains graves dating to the 1700s.The property was listed on the National Register of Historic Places in 1978.

Schley (pronounced Shly) is an unincorporated community, in Orange County, North Carolina, United States, located southwest of Caldwell and northeast of Hillsborough. It lies at an elevation of 584 feet (178 m). One of the main landmarks in the area is the Schley Grange Hall at the intersection of Hwy 57 and Schley Road. Schley has a very active farming community.

Rigsbee's Rock House is a historic home and national historic district located near Hillsborough, Orange County, North Carolina. The house was built in 1929, and is a 1+1⁄2-story, rectangular, white flint rubble dwelling with a steeply pitched hipped roof in the Tudor Revival style. The house was restored in 1986–1987. Also on the property are the contributing original two car, detached garage, a pump house, and an outdoor swimming pool, each constructed of white flint rock.It was listed on the National Register of Historic Places in 1988.

Occoneechee Speedway was one of the first two NASCAR tracks to open. It closed in 1968 and is the only dirt track remaining from the inaugural 1949 season.It is located just outside the town of Hillsborough, North Carolina.

Cabe-Pratt-Harris House, also known as Riverland Farm, is a historic home located near Hillsborough, Orange County, North Carolina. It was built about 1820, and is a 1+1⁄2-story, Late Georgian style frame dwelling with a gable roof. It sits on a raised fieldstone foundation and has flanking stone chimneys with brick stacks. It has a rear addition built in the 1940s, and was renovated in the 1980s.It was listed on the National Register of Historic Places in 1999.

Orange High School is a high school in the northern area of Orange County, North Carolina.

Sans Souci is a historic home located at Hillsborough, Orange County, North Carolina. It was built about 1813, as two-story, three-bay, frame dwelling with a gable roof and set on a brick foundation. Later additions included 1+1⁄2-story flanking wings added in the Federal period and a Greek Revival shed addition built in the mid-19th century across the rear of the main block and the east wing. Also on the property are the contributing kitchen, office, and servant's quarters.It was listed on the National Register of Historic Places in 1971. It is located in the Hillsborough Historic District.

Ayr Mount is a Federal style plantation house located east of Hillsborough, in Orange County, North Carolina, the United States of America. In 1799, William Kirkland (born in Ayr, Scotland) bought 500 acres (2.0 km2) east of Hillsborough. Circa 1815, he had a home built for himself, his wife, Margaret, and their children, a brick dwelling with a two-story, three-bay main block flanked by one-story, two-bay wings. A full-width front porch, added about 1894, was removed sometime after 1971 and replaced with a facsimile of the original porch.Mrs. Samuel (Emily) Kirkland, the last of four generations of Kirklands to occupy the house, lived there until 1985. The property had gone through several owners prior to Kirkland's purchase of the property, the most well-known being William Few, Jr., whose father, William Few, Sr., had a house built on the property c. 1764. Today, Ayr Mount is a publicly accessible historic site located on 265 acres (1.07 km2). It is owned and operated by Classical American Homes Preservation Trust. The home has been furnished with Federal period antiques and decorative art, including some original Kirkland furnishings. Ayr Mount features guided house tours and the one-mile (1.6 km) hiking trail the "Poet's Walk."

Old Orange County Courthouse is a historic courthouse building located at Hillsborough, Orange County, North Carolina. It was built in 1845, and is a two-story, Greek Revival style, temple-form brick structure. It replaced Dickerson Chapel as the county's courthouse. The front facade features a Doric order tetrastyle pedimented portico and two-stage clock tower. The building served as the seat of Orange County's government until 1954, when a new building was completed.It was listed on the National Register of Historic Places in 1971. It is located in the Hillsborough Historic District.

Captain Benjamin Merrill (c. 1731 – June 19, 1771) was an American military officer, gunsmith and planter who served in the militia of Rowan County, North Carolina. He sided with the Regulator Movement during the American Revolution. He was captured following the conflict ending Battle of Alamance on May 16, 1771, and shortly thereafter ordered to be executed as a rebel and traitor by Governor William Tryon.

St. Matthew's Episcopal Church and Churchyard is a historic Episcopal church located on St. Mary's Road, Hillsborough, Orange County, North Carolina. The first three bays of the Gothic Revival-style brick church were built between 1825 and 1826, and its rear was extended by another bay in 1868. It features a square entrance tower built in 1830, which was rebuilt in 1850. The tower has a pyramidal spire and lancet windows.The property was listed on the National Register of Historic Places in 1971. It is located in the Hillsborough Historic District.