Jacob Jackson Farm

Holden–Roberts Farm, also known as Rolling Acres Farm, is a historic home and farm and national historic district located near Hillsborough, Orange County, North Carolina. The farmhouse was built in 1873–1874, and is a two-story, frame I-house, with modest Greek Revival style detailing. The house is sheathed in weatherboard, has a gable roof, and features two stately single-shouldered end chimneys. Also on the property are the contributing granary (c. 1900), three frame chicken houses (c. 1910), a brick shed-roofed garden house (c. 1915), an equipment shed (c. 1930), and two pole barns (c. 1950). The house was built for Addison Holden, half-brother of North Carolina's Reconstruction Governor William Woods Holden.It was listed on the National Register of Historic Places in 2002.

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.

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.

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."

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.

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.

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.

Hillsborough Historic District is a national historic district located at Hillsborough, Orange County, North Carolina. The district encompasses 529 contributing buildings, 9 contributing sites, 13 contributing structures, and 2 contributing objects in the central business district and surrounding residential sections of Hillsborough. The district includes buildings dating to the late-18th and early-20th century and includes notable examples of Federal, Greek Revival, and Italianate style architecture. Located in the district are the separately listed Burwell School, Eagle Lodge, Hazel-Nash House, Heartsease, Montrose, Nash Law Office, Nash-Hooper House, Old Orange County Courthouse, Poplar Hill, Ruffin-Roulhac House, Sans Souci, and St. Matthew's Episcopal Church and Churchyard. Other notable buildings include Seven Hearths, the Presbyterian Church (1815-1816), Methodist Church (1859-1860), First Baptist Church (1862-1870), Twin Chimneys, and the Berry Brick House.It was listed on the National Register of Historic Places (NRHP) in 1973.

Ruffin-Roulhac House, also known as Little Hawfields, is a historic home located at Hillsborough, Orange County, North Carolina, United States. It was built about 1820, and is a 1+1⁄2-story, five-bay, frame dwelling including a two-room addition built about 1830. It is topped by a gable roof, is sheathed in weatherboard, and has a one-bay 20th century replacement porch. The interior has Federal, Greek Revival, and Victorian style design elements. It was the home of jurist Thomas Ruffin (1787–1870) from after the end of the American Civil War until his death in 1870.The house has since been converted into town offices for the town of Hillsborough.It was listed on the National Register of Historic Places in 1971. It is located in the Hillsborough Historic District.

Dickerson Chapel is a historic chapel in Hillsborough, North Carolina. Built in 1790, the chapel originally served as the courthouse for Orange County until 1844. It housed a Baptist congregation from 1845 until 1862, when it was purchased by a group of Quakers to serve as a school for African-American children. Since 1886 it has housed a congregation of the African Methodist Episcopal Church.