Willow Grove Inn

Willow Grove, also known as the Clark House, is a historic plantation house located near Madison Mills, Orange County, Virginia. The main brick section was built about 1848, and is connected to a frame wing dated to about 1787. The main section is a 2+1⁄2-story, six-bay, Greek Revival-style brick structure on a high basement. The front facade features a massive, 2+1⁄2-story, tetrastyle pedimented portico with Tuscan order columns, a full Tuscan entablature, an arched brick podium, and Chinese lattice railings. Also on the property are numerous 19th-century dependencies and farm buildings, including a two-story schoolhouse, a one-story weaving house, a smokehouse, and a frame-and-stone barn and stable.It was listed on the National Register of Historic Places in 1979.

Madison Mills is an unincorporated community located in Madison County, Virginia, United States. It is located at the intersection of U.S. Route 15 and Virginia State Route 230. Greenway and Willow Grove are listed on the National Register of Historic Places.

Greenway, also known as Prospect Hill, is a historic home and farm complex located at Madison Mills, Madison County, Virginia. The original section was built about 1780, and is a 1+1⁄2-story, heavy timber-frame structure, on a hall-and-parlor plan. A shed-roofed rear addition was added shortly before 1800. A rear wing was added in the early-20th century and enlarged in 1986. Also on the property are the contributing wood frame dairy / maids house; brick dairy / smokehouse; pumphouse (c. 1920); garage, corncrib, and the Madison/Taliaferro family cemetery. Greenway was built by Francis Madison, brother of President James Madison.It was listed on the National Register of Historic Places in 1988.

Grelen is a historic home located near Orange, Orange County, Virginia. The main house was built in 1935–1936, and consists of a 2+1⁄2-story, five-bay, brick Georgian Revival style main block flanked by 1+1⁄2-story brick wings. The house is topped by a slate hipped roof and has a recessed centrally located six-panel front door surrounded by fluted pilasters. It features two massive interior brick chimneys with corbeled caps that rise above the roof of the main block of the house.It was listed on the National Register of Historic Places in 1998.

Woodberry Forest School is a private, all-male boarding school located in Woodberry Forest, Madison County, Virginia, in the United States. Woodberry's current enrollment is 391. Students come from 34 U.S. states, Washington, D.C., and 36 countries. The school's endowment and managed funds total $432,000,000 as of June 30, 2023. Comprehensive tuition for 2023–2024 is $65,350; 41% of the students receive financial aid.

The Residence, also known as Woodberry, is a historic home located on the grounds of Woodberry Forest School at Woodberry Forest, Madison County, Virginia. It was built in 1793, reputedly after the plans of Thomas Jefferson. In 1884, the house was extensively enlarged and altered. It is a 1+1⁄2-story, wood frame, Federal-style residence. The front facade features a pedimented Tuscan order portico. The house is covered with weatherboarding and is topped by its original hipped roof. Also on the property is the contributing smokehouse. The house was built for William Madison, brother of President James Madison.It was listed on the National Register of Historic Places in 1979.

Five Forks is an unincorporated community located in Madison County, Virginia, United States.

Orange High School is a historic school located in Orange, Virginia. The first school building at the site was built in 1911 based on a design by noted Virginia architect Charles M. Robinson. The original structure is a 2+1⁄2-story building with a monumental Doric portico modeled on the Temple of Albano. In 1925, a one-story annex was added to the school. The school opened in 1911 as an elementary, middle, and high school. It continued in operation until 1970. When plans to demolish the original 1911 building were announced in the late 1990s, local residents protested. The property was converted for use as apartments for senior citizens.The building was listed on the National Register of Historic Places in 2001.

Brampton, also known as Buena Vista Farm, is a historic home located near Orange, in Madison County, Virginia. It was built about 1846, as a two-bay, side passage plan with a flat roof, two-story portico, and a small wing. It is a temple-form Greek Revival-style residence. A rear addition was built about 1900, and the front portico was redesigned with a pedimented form. Also on the property are the contributing brick kitchen, smokehouse, and dairy.It was listed on the National Register of Historic Places in 1985.

Williston is a historic home and farm complex located near Orange, Orange County, Virginia. It was built in 1867, and is a two-story, three-bay, Italianate style brick dwelling. The front facade features a tall portico with paired fluted polygonal columns set on pedestals. The interior features stenciled and painted murals on the dining room walls. Also on the property are the contributing smokehouse, hen house, servant's house, carriage house, granary and the foundation and lean-to of what was formerly a late-19th century barn.It was listed on the National Register of Historic Places in 2005.

Formerly called the Doctor Holladay House, the Holladay House in Orange, Virginia (c.a. 1830) is on the nationally recognized Journey Through Hallowed Ground. Named for Dr. Lewis Holladay, a prominent Virginia physician, the Holladay House has witnessed almost two centuries of American history. The building is historically significant because it is one of only a few antebellum structures still standing in Orange, Virginia. Since approximately 1830, the Holladay House has served as a mercantile store, a residence, a doctor’s office, and a Virginia bed and breakfast inn. In the early 20th century, a private schoolhouse for local children was also on the property. Only a handful of proprietors have owned the home, and the Holladay family was its steward for over 100 years. The Holladay House still boasts much of its original woodwork, including floors, mantels, doors and period antiques from the Holladay family. The Holladay House is one of the two oldest standing structures in historic downtown Orange, and is a contributing property to the Orange Commercial Historic District, listed on the National Register of Historic Places. It has been a landmark on Main Street for generations.

Rebel Hall is a historic plantation house located at Orange, Orange County, Virginia. It was built in 1848–1849, and is a two-story, three-bay, Greek Revival style brick dwelling. It sits on a raised brick basement and has a shallow-pitched, standing-seam metal roof. A rear wing was added about 1900.It was listed on the National Register of Historic Places in 2002.