Rose Hill, Albemarle County, Virginia

Monticello is an American Viticultural Area (AVA) located in the central Piedmont region of the Commonwealth of Virginia. It was established by the Bureau of Alcohol, Tobacco and Firearms (ATF) on February 22, 1984 after six wine grape growers in the Charlottesville area petitioned the ATF to designate a viticultural area to be known as “Monticello.” The name "Monticello" is known nationally and locally as the historic home of Thomas Jefferson, located near the center of the area. Monticello AVA includes most of Albemarle, Fluvanna, Greene, Orange, and Nelson counties. The area is nestled along the eastern slopes of the Blue Ridge Mountains and encompasses the small ridge known as the Southwest Mountains. There are approximately 30 varieties of grapes grown in the Monticello AVA. However, the most notable grapes grown in the area include Cabernet Franc, Chardonnay and Viognier. The hardiness zone is 7a except in some higher vineyards which are 6b. In 2019, the Tax and Trade Bureau (TTB) granted a petition to expand the AVA by approximately 106,240 acres (166 sq mi) into Fluvanna County.

Tufton Farm, located in Albemarle County, Virginia, borders the Monticello plantation. The farm was passed down from Peter Jefferson to his son Thomas Jefferson, whose grandson Thomas Jefferson Randolph inherited the property. Thomas Jefferson experimented with plants and sustainable farming. It is now the site of the Thomas Jefferson Center for Historic Plants.

Shadwell is a census-designated place (CDP) in Albemarle County, Virginia. It is located by the Rivanna River near Charlottesville. The site today is marked by a Virginia Historical Marker to mark the birthplace of President Thomas Jefferson. It is listed on the National Register of Historic Places along with Clifton.Before early colonists moved into the Shadwell area, Monacan people had trails that traversed what became Shadwell. Peter Jefferson, the father of President Thomas Jefferson established and named the Shadwell plantation in the mid-18th century. Four generations of the Jefferson family lived at Shadwell. Initially, it was a plantation worked by enslaved and free people and grew tobacco, grain, and clover. Then, a grist mill, sawmill, and carding factory expanded the Shadwell economy. Canals and locks were constructed in the Rivanna River to transport goods, including lumber, flour, grain, and cotton-yard. After the carding factory burned down in the 1850s and the Louisa Railroad was completed, Shadwell began to decline economically. After that, the Shadwell estate became a farm, operated by Downing Smith. In 1991, an archaeological study found remnants of foundations and cellars of two houses, one of which is believed to be the original Jefferson house. Located within the Shadwell, Virginia area are the Clifton and Edge Hill historic homes.

Milton is an unincorporated community in Albemarle County, Virginia. In the batteaux era Milton was the head of navigation along the river, but by the mid-nineteenth century horse-drawn canal boats were traveling all the way upstream to Charlottesville, where the head of navigation was located at the very point where the Fredericksburg Road (now VA 20) and Three Chopt Road (U.S. Route 250).

Simeon is an unincorporated community in Albemarle County, Virginia.Morven, Highland, and Sunnyfields are listed on the National Register of Historic Places.

Clifton is a historic home located near Shadwell, Albemarle County, Virginia. It was built about 1800, and is a large, rambling two-story, five-bay, wood frame dwelling. The house has later 19th- and 20th-century Colonial Revival-style additions and alterations. The front facade features a double level porch, added about 1930, and the interior has Federal details. Also on the property are the contributing brick office (c. 1833–1845); the ruins of an early 19th-century spring house; the shaft of a 19th-century stone-lined ice house; an early 20th-century chicken coop and an altered 1920s brick garage.Clifton was built by Congressman and Virginia Governor Thomas Mann Randolph, Jr. (1768–1828), who was married to Martha Jefferson, the daughter of President Thomas Jefferson. It was part of the never-to-be port of North Milton, a sister port to the now extinct village of Milton directly across the Rivanna River. With his partners, Randolph planned North Milton to support commercial and agricultural development, situated along the Milton Canal of the Rivanna River. The Clifton house first began as a warehouse and Randolph had a separate office building, which is still on the Clifton grounds. The house was expanded later and during the 19th century it had a one-story veranda, which has been replaced by the portico. Situated on 100 acres, it has operated as an inn since 1983. It was added to the National Register of Historic Places in 1989.

StreamWatch is an environmental monitoring program focused on the 766-square-mile (1,980 km2) Rivanna River watershed in central Virginia in the United States. The data StreamWatch collects helps communities in the city of Charlottesville and in Albemarle, Fluvanna, and Greene gauge stream conditions and to inform planning and environmental management decisions.StreamWatch was founded in 2002 as a joint project of The Nature Conservancy, the Rivanna Conservation Society, the Thomas Jefferson Soil and Water Conservation District, the Rivanna River Basin Commission and the Thomas Jefferson Planning District Commission. Conservation groups. Benthic invertebrate (see bioindicator), sedimentation, stream habitat, and other types of data are collected by volunteers and professionals using established scientific protocols. StreamWatch tracks land-use data, including data about agriculture, forestry, and residential and commercial development. Fieldwork, interpretation, and reporting are guided by a technical advisory committee composed of academic and resource agency scientists. StreamWatch also compiles Rivanna watershed data collected by other organizations.

Edge Hill, also known as Edgehill and Edgehill Farm, is a historic house located near Shadwell in Albemarle County, Virginia, United States.

Sunnyfields is a historic home located between Monticello and Ash Lawn-Highland near Simeon, Albemarle County, Virginia. It was built in 1833, and is a two-story, nearly square brick structure painted white. It has a two-story corner tower, dating to either from just before or just after the American Civil War, and two-story, frame wing. Also on the property is a contributing servants' cottage. It was designed and built by William B. Phillips, who was employed by Thomas Jefferson as principal builder at the University of Virginia.It was added to the National Register of Historic Places in 1993.

Highland, formerly Ash Lawn–Highland, located near Charlottesville, Virginia, United States, and adjacent to Thomas Jefferson's Monticello, was the estate of James Monroe, a Founding Father and fifth president of the United States. Purchased in 1793, Monroe and his family permanently settled on the property in 1799 and lived at Highland for twenty-five years. Personal debt forced Monroe to sell the plantation in 1825. Before and after selling Highland, Monroe spent much of his time living at the plantation house at his large Oak Hill estate near Leesburg, Virginia. Monroe named his Charlottesville home "Highland". For many years after Monroe's death until 2016, the house was known as Ash Lawn-Highland or merely Ash Lawn. The estate is now owned, operated and maintained by Monroe's alma mater, the College of William & Mary.

Monticello ( MON-tih-CHEL-oh) was the primary plantation of Thomas Jefferson, a Founding Father and the third president of the United States, who began designing Monticello after inheriting land from his father at age 14. Located just outside Charlottesville, Virginia, in the Piedmont region, the plantation was originally 5,000 acres (20 km2), with Jefferson using the labor of African slaves for extensive cultivation of tobacco and mixed crops, later shifting from tobacco cultivation to wheat in response to changing markets. Due to its architectural and historic significance, the property has been designated a National Historic Landmark. In 1987, Monticello and the nearby University of Virginia, also designed by Jefferson, were together designated a UNESCO World Heritage Site. The current nickel, a United States coin, features a depiction of Monticello on its reverse side. Jefferson designed the main house using neoclassical design principles described by Italian Renaissance architect Andrea Palladio and reworking the design through much of his presidency to include design elements popular in late 18th-century Europe and integrating numerous ideas of his own. Situated on the summit of an 850 ft-high (260 m) peak in the Southwest Mountains south of the Rivanna Gap, the name Monticello derives from Italian meaning "little mountain". Along a prominent lane adjacent to the house, Mulberry Row, the plantation came to include numerous outbuildings for specialized functions, e.g., a nailery; quarters for slaves who worked in the home; gardens for flowers, produce, and Jefferson's experiments in plant breeding—along with tobacco fields and mixed crops. Cabins for slaves who worked in the fields were farther from the mansion.At Jefferson's direction, he was buried on the grounds, in an area now designated as the Monticello Cemetery. The cemetery is owned by the Monticello Association, a society of his descendants through Martha Wayles Skelton Jefferson. After Jefferson's death, his daughter Martha Jefferson Randolph, apart from the small family graveyard, sold Monticello for $7,500. In 1834, it was bought by Uriah P. Levy, a commodore in the U.S. Navy, for $2,500, (~$78,667 in 2022) who admired Jefferson and spent his own money to preserve the property. His nephew Jefferson Monroe Levy took over the property in 1879; he also invested considerable money to restore and preserve it. In 1923, Monroe Levy sold it for $500,000 (~$6.72 million in 2022) to the Thomas Jefferson Foundation (TJF), which operates it as a house museum and educational institution.

Rivanna is a census-designated place (CDP) in Albemarle County, Virginia, just east of Shadwell. The population as of the 2010 Census was 1,860. It consists mainly of the Glenmore gated community.