Williston (Orange, Virginia)

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.

The Wreck at the Fat Nancy was one of the largest railroad disasters in Virginia's history. On the morning of July 12, 1888, the incident occurred when a trestle collapsed as a passenger train was atop it. Virginia Midland Railroad's Train 52—"The Piedmont Airline"—was crossing the 44-foot-high (13 m), 487-foot-long (148 m) trestle known as the "Fat Nancy" when it gave way, sending the train to the ground. By 1888, many states had experienced memorable wrecks with high death tolls. Though Virginia newspapers were full of reports of small train accidents, there were typically few deaths. The wreck at Fat Nancy was Virginia's first experience with a train crash that resulted in multiple deaths and large-scale injuries. Five passengers, one rail employee, one mail clerk, and one newsboy were killed and another mail clerk died from his injuries the following day. At least twenty-six were injured, though some reports list a higher number.The incident is named for the trestle, known as the "Fat Nancy" for the woman who served as the trestle watcher. The trestle's official name was Browning Trestle, for the owners of the property on which it sits, or Two-Runs trestle for the creek that ran below. A local African-American woman who waved to train conductors and occasionally received a shovelful of coal inspired locals to rename the trestle as Fat Nancy's trestle. The Baltimore Sun reported that the woman's actual name was Emily Jackson and described a woman of "great size and uncouth appearance."One of the deceased was Cornelius G. Cox, the civil engineer who had designed a culvert to replace the trestle, which was known to be unstable. After the collapse, the area was filled with earth and a granite culvert placed over the stream, per his design. One of the surviving passengers was former Confederate Lieutenant General James Longstreet, who was returning from the 25th reunion of the Battle of Gettysburg.The culvert that replaced the trestle still stands today, where it allows Laurel Creek to flow through. Tracks no longer cross the culvert—they're now to the south. The Virginia Department of Historic Resources erected a historical marker at the site of the wreck, along Virginia State Route 20, in 2007. A keystone at the top of the arched tunnel is marked "In memory of Cornelius Cox."

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.

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.

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.

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.

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.

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.

Orange County Courthouse is a historic courthouse complex located at Orange, Orange County, Virginia. It was built in 1858–1859, and is a 1 1/2-story, Italian Villa style brick structure. The front facade features a three-part arcade consisting of a semi-elliptical arch flanked by small semicircular arches. Above the arcade is a three-stage tower consisting of the main entrance as the first stage; a clock, installed within existing round windows in 1949, as the second stage; and arched openings with louvres covered by a shallow hip roof and topped by a finial complete the tower. Associated with the courthouse are the contributing clerk's office (1894) and jail (1891).It was listed on the National Register of Historic Places in 1979. 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.

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.

Orange is a town and the county seat of Orange County, Virginia, United States. The population was 5,062 at the 2020 census, representing a 7.2% increase since the 2010 census. Orange is 28 miles (45 km) northeast of Charlottesville, 88 miles (142 km) southwest of Washington, D.C., and 4 miles (6 km) east of Founding Father and fourth U.S. president James Madison's plantation of Montpelier.