Tims River

Black Meadow (now known as "Wolftrap Farm") is a historic plantation house and farm complex located near Gordonsville, Orange County, Virginia. The house was built in 1856, and is a 1+1⁄2-story, three-bay, Greek Revival style dwelling with a front gable roof. It was renovated in 1916, with the addition of a two-story wood-frame ell and realignment of interior spaces. Also on the property are the contributing milk house (c. 1916), slave quarters (c. 1856), a dairy barn (c. 1943), a bent barn/stable (c. 1856), a multiuse barn/shed (c. 1856), and a tenant house (c. 1943).Black Meadow was one of the outlying farms owned and cultivated by James and Dolley Madison, whose Montpelier home lies just a few miles northwest. It was listed on the National Register of Historic Places in 2005.The farm, known since the mid-1970s as Wolftrap Farm, is now operated as a wedding and events venue and seven homes on the farm are available as vacation rentals.

Berry Hill is a historic home located near Orange, Orange County, Virginia. It was built in 1827, and is a 2+1⁄2-story, brick dwelling with a standing-seam metal gable roof. It consists of an arcaded pavilion in the main section with a west wing. It was built by William B. Philips a master mason employed by Thomas Jefferson during the construction of the University of Virginia.It was listed on the National Register of Historic Places in 1980.

Mayhurst is an 1859 Italianate mansion in Orange, Virginia. It was built by the Willis family relatives of President James Madison as the plantation house for an estate comprising 2,500 acres (10 km2) of fields, pastures and forest. It was a scene of action in the Civil War. It is currently operated as an Inn.

Rockwood is a historic house in the vicinity of Montpelier Station, Orange County, Virginia. It was built in 1848 and is a 2+1⁄2-story frame house which was designed in a blend of the Gothic Revival and Greek Revival styles. The house sits on a brick English basement and has an offset sharply pitched cross-gable roof.It was added to the National Register of Historic Places on July 5, 2001.

Greenwood is a historic home located near Orange, Orange County, Virginia. It was built about 1820, and is a two-story, three-bay, timber frame Federal style I-house with a side gable roof. It has a center-passage plan, a raised basement, and two exterior-end chimneys. The Greek Revival style front entry porch has brick piers supporting a one-story wooden porch with a gable roof and triangular pediment supported by square paired columns. A one-bay, single-pile timber-frame wing addition, built about 1850. Also on the property are a contributing outbuilding, well, and the grave of Mary Roberta Macon who died at age nine in 1847.It was listed on the National Register of Historic Places in 1992.

Chestnut Hill is a historic home located at Orange, Orange County, Virginia. It was built about 1860, and is a two-story, frame dwelling in a combination of the Italianate and Greek Revival styles. A Second Empire style mansard roof was added in 1891. The front facade features a central, one-story, one-bay porch with a balustraded deck above and balustraded decks with the same scroll-sawn balusters across the front. The historic floor plan is a double-pile center-passage plan with two interior chimneys serving four fireplaces on each floor. The house was moved to a new location, 150 feet away from its original site, when threatened with demolition in 2003. Also on the property is a small, one-story, single-bay, 19th-century contributing shed.It was listed on the National Register of Historic Places in 2009.

Orange County High School is a public high school for students grades 9-12 located in Orange, Virginia.

The James Madison Museum located in Orange, Virginia is a museum dedicated to 4th president of the United States James Madison and his wife, Dolley Madison. Exhibits include original furniture used by James Madison, his personal items, portraits of the Madisons, and a statue.Due to Madison's reputation as a farmer, the museum also features a collection of antique farm tools. There is also a partially reconstructed 1733 house to demonstrate building practices.

St. Thomas Church is a historic Episcopal church located at Orange, Virginia, United States. It is a rectangular brick structure measuring 40 feet wide and 105 feet deep. The front facade features a recessed portico with two Doric columns flanked by two Doric pilasters. Atop the gable roof is a three-stage tower topped by an octagonal cupola. The original church building was built in 1833–1834, and measured approximately 40 feet wide and 65 feet deep. It was built by William B. Philips, a master mason employed by Thomas Jefferson during the construction of the University of Virginia. It was enlarged and improved in 1853, and enlarged again in 1912. In 1928, the rear addition was raised to a full two stories and a parish hall constructed. The original church is believed to have been based on the plans by Thomas Jefferson for Christ Church in Charlottesville, Virginia. That church was demolished in 1895.It was added to the National Register of Historic Places in 1976. It is located in the Orange Commercial Historic District.

Orange Commercial Historic District is a national historic district located at Orange, Orange County, Virginia. One of Virginia's Main Street communities, it encompasses 61 contributing buildings in the central business district of Orange's county seat.

Ballard–Marshall House, also known as Marshall House, is a historic home located at Orange, Orange County, Virginia. It was built in 1832, and is a two-story, three-bay, brick late Federal Virginia townhouse dwelling. It is an example of an urban house form influenced by the Jeffersonian Classical style. A two-story rear addition was added about 1900, and the original front and side porches were replaced with ones in the Colonial Revival style in 1910. The house was converted to apartments in 1934–1935, and renovated in 1986–1988.It was listed on the National Register of Historic Places in 1988.

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.