Chessie Nature Trail

Lexington and Covington Turnpike Toll House is a historic toll house located at Lexington, Virginia. The original section was built about 1834, as a two-room brick structure. A board-and-batten frame was added between 1865 and 1867. Two additional rooms were added to the original structure in the 1870s, forming a "U"-shape. In 1887, a Victorian style front porch was added to the original brick structure. The house was sheathed in weatherboard in 1904, and an addition filling in the "U" was added. The house was rehabilitated between 1997 and 2004. Also on the property are the contributing ruins of a spring house. The building housed a toll house into the 1850s, then became a dwelling.It was listed on the National Register of Historic Places in 2004.

Reid–White–Philbin House, also known as Evergreen House, is a historic home located at Lexington, Virginia. It was built in 1821, and is a two-story, Federal style brick dwelling. It features an early entry porch supported by Ionic order columns A two-story brick addition was made to the left-hand gable end in 1847. The addition has a two-tier front portico and a post-bellum conservatory with bay window. Attached to the rear is a 1+1⁄2-story stone kitchen wing dated to the second half of the 18th century. Also on the property is a contributing early- to mid-19th century dependency. It was built for locally prominent businessman, educator, and politician Samuel McDowell Reid.It was listed on the National Register of Historic Places in 2000. It is located in the Lexington Historic District.

Mulberry Hill is a historic house located at Lexington, Virginia. It was built in at least four different building periods that range from the late-18th century to the early 20th century. The original section was built about 1798. It two-story, five bay, brick dwelling with a four-room, double-pile, central-passage plan. Its hipped roof was added about 1903. The interior features unusually elaborate though provincial Georgian woodwork and plasterwork in the principal rooms.It was listed on the National Register of Historic Places in 1982. It has been the headquarters of Kappa Alpha Order, a college fraternity that was founded next door at Washington and Lee University, since 2004.

The Oak Grove Cemetery, originally known as the Presbyterian Cemetery, is located on South Main Street in downtown Lexington, Virginia, less than a mile from the campuses of Washington and Lee University and the Virginia Military Institute. The cemetery was renamed in 1949 as the Stonewall Jackson Memorial Cemetery after the Confederate general, who was buried here in 1863. The current name dates to September 3, 2020. Also buried here are 144 Confederate veterans, two Governors of Virginia, and Margaret Junkin Preston, the "Poet Laureate of the Confederacy".

The Washington and Lee University Historic District is a National Historic Landmark District encompassing the historic core elements of the campus of Washington and Lee University in Lexington, Virginia. The campus's Colonnade constitutes one of the nation's finest assemblages of Classical Revival educational buildings, and includes Washington Hall, the school's oldest surviving building. The district also includes University Chapel, itself a National Historic Landmark. The district was listed in 1971.

Washington and Lee University (Washington and Lee or W&L) is a private liberal arts college in Lexington, Virginia. Established in 1749 as Augusta Academy, it is among the oldest institutions of higher learning in the United States. Washington and Lee's 325-acre campus sits at the edge of Lexington and abuts the campus of the Virginia Military Institute in the Shenandoah Valley region between the Blue Ridge Mountains and the Allegheny Mountains. The institution consists of three academic units: the college itself; the Williams School of Commerce, Economics, and Politics; and the School of Law. It hosts 24 intercollegiate varsity athletic teams which compete as part of the Old Dominion Athletic Conference of the National Collegiate Athletic Association (NCAA Division III).

Lexington Presbyterian Church is a historic Presbyterian church building at Main and Nelson Streets in Lexington, Virginia. It was designed by architect Thomas U. Walter in 1843, and completed in 1845. A rear addition was built in 1859; stucco added in the 1880s; the building was renovated and enlarged in 1899; and the Sunday School wing was added in 1906. It is a monumental "T"-shaped, temple form stuccoed brick building in the Greek Revival style. The front facade features a Greek Doric pedimented peristyle portico consisting of six wooden columns and a full entablature. The building is topped by a tower with louvered belfry and spire.Starting in 1851, Stonewall Jackson was a member of the church and taught Sunday school. In 1863 he was buried in the church's cemetery which is now named for him.It was listed on the National Register of Historic Places in 1979. It is in the Lexington Historic District.

Lexington is an independent city in Virginia, United States. At the 2020 census, the population was 7,320. It is the county seat of Rockbridge County, although the two are separate jurisdictions, and is combined with it for statistical purposes by the Bureau of Economic Analysis. Lexington is about 57 miles (92 km) east of the West Virginia border and is about 50 miles (80 km) north of Roanoke, Virginia. First settled in 1778, Lexington is best known as the home of the Virginia Military Institute and Washington and Lee University.

Alexander–Withrow House is a historic home located at Lexington, Virginia. It was built about 1790, and significantly modified in the 1850s when the street was lowered by about 10 feet. The upper stories of diaper patterned brick sit on a first level of limestone. It has a shallow hipped roof and four corner chimneys. The original front entrance opens onto a small balcony with a decorative cast-iron balustrade supported on large cast-iron brackets. The house was renovated by the Historic Lexington Foundation in 1969–1970.It was listed on the National Register of Historic Places in 1971. It is located in the Lexington Historic District.

University Chapel (formerly Lee Chapel) of Washington and Lee University is a National Historic Landmark in Lexington, Virginia. It was constructed during 1867–68 at the request of Robert E. Lee, who was president of the school (then known as Washington College), and after whom the university is, in part, named. The Victorian brick architectural design was probably the work of Lee's son, George Washington Custis Lee, with details contributed by Col. Thomas Williamson, an architect and professor of engineering at the neighboring Virginia Military Institute. Upon completion and during Robert E. Lee's lifetime it was known as the College Chapel. Lee was buried beneath the chapel in 1870.

The Stonewall Jackson House, located at 8 East Washington Street in the Historic District of Lexington, Virginia, was the residence of Confederate general Thomas "Stonewall" Jackson from 1858 to 1861.

The Washington and Lee University School of Law (W&L Law) is the law school of Washington and Lee University, a private liberal arts college in Lexington, Virginia. It is accredited by the American Bar Association. Facilities are on the historic campus of Washington and Lee University in Sydney Lewis Hall. W&L Law has a total enrollment of approximately 365 students in the Juris Doctor program and a 6-to-1 student to faculty ratio.