Monroe purchased the original 1,000 acres of Highland from Champe and Maria Carter in 1793, dividing it from their Blenheim plantation, which was itself part of a 9,350-acre land grant to John Carter in 1730. Monroe acquired the land to be near his friend and mentor Thomas Jefferson, whose Monticello was adjacent to the north. At the time he purchased Highland, Monroe and his family were living on another property he owned in Albemarle County, a tract of 800 acres known as Monroe Hill now at the heart of the University of Virginia.
Shortly after purchasing the Highland tract, Monroe departed for Paris to serve as minister to France. During Monroe’s time in Paris, Jefferson, James Madison, and Monroe’s maternal uncle Joseph Jones were tasked with constructing a house and developing the plantation. Construction was delayed during Monroe’s absence, however, and work on the main house wasn’t begun until his return from France in 1797. The house was completed in 1799, and the Monroe family moved there in November of that year.
There are no extant drawings of the house, but Monroe referred to it as modest, calling it a “cabbin castle.” In an 1800 insurance policy declaration, he described it as a “Wooden Dwelling house, the Walls filled with Brick, one story high 40 feet long by 30 feet wide” with a one-story kitchen wing “34 by 18 ft.” This would have made it a substantial house for the era, but not as grand as the nearby estates built by his close associates Jefferson and Madison. He also continued to expand his land holding by buying parcels adjacent to his property, eventually enlarging the plantation to 3,500 acres.
Monroe was inaugurated to his first term asin March 1817. In 1818, he ordered the construction of a two-room guesthouse with a lobby entrance just below the main house, presumably to accommodate increased numbers of visitors, and gave the property the name of Highland. As with most of the work at Highland, the construction of the guesthouse was done by enslaved laborers. Research has identified them as Peter Malorry and George Williams.
James Monroe’s Plantation in Loudoun County
This Federal-style 1822 mansion, built by enslaved labor, was the main house at Oak Hill, the Loudoun County plantation that belonged to James Monroe, the fifth president of the United States.
In this advertisement published in the March 9, 1826, edition of the Richmond Enquirer newspaper, James Monroe offers for sale his Albemarle County plantation, Highland. He describes the 8,500-acre tract of land as being "of good quality, and remarkably well timbered and watered," and sited along the south side of the Rivanna River. The property includes "a commodious dwelling house, buildings for servants, and other domestic purposes, good stables, two barns, with threshing machines, a grist and saw mill, with good houses for managers and laborers ... and all in good repair." Monroe also offers for sale two other Albemarle County farms of a much smaller size.
Monroe wrote the advertisement at Oak Hill, his plantation in Loudoun County, which was closer to Washington D.C. and boasted a much grander residence than the one at Highland. Monroe probably purchased ads in the newspaper for a certain block of time, because by the publication date above he had already sold 907 core acres of Highland along with the main house and outbuildings. The deed for that sale was dated January 1, 1826.
By the late 1810s, Monroe was increasingly spending time at his Loudoun County residence, Oak Hill, which was grander in style and closer to Washington, D.C. In 1823, he listed Highland for sale to pay off the debts he had accumulated in his years of public service. The estate was described as comprising a “commodious dwelling house, buildings for servants and other domestic purposes, good stable, two barns with threshing machine, a grist and sawmill with houses for managers and laborers . . . all in good repair.” In a deed of sale dated January 1, 1826, the core 907 acres of Highland, with house and outbuildings, were sold to Edward Goodwyn. The remainder of the property was sold through the Bank of the United States in 1828 to pay off the residual of Monroe’s debt to the bank. The main house at Highland subsequently burned to the ground, likely sometime in late 1829 or early 1830. Goodwyn sold Highland to Bernard H. Buckner in 1834, and Alexander Garrett purchased the property from him in 1837, changing its name to Ash Lawn.
Over time, the various owners of Ash Lawn added to Monroe’s modest guesthouse. In the 1840s, a porch was added to, or replaced on, the south front. In the 1850s, a one-story addition with a basement was added to the east side. In 1867,purchased the property and in 1873 built a new main house attached to the east side of the 1850s addition, turning the extant buildings into the rear wing of his home. The Massey house, fronted with boxwood-lined colonial revival gardens, became the dominant feature of Ash Lawn. By the late-nineteenth century, it was widely believed that the guesthouse was a remnant wing of the original Monroe home. In September 1885, the magazine The Campaign said in an article about Massey and Ash Lawn, “The main building is new, the old Monroe house having been nearly destroyed by fire. There remains yet in use a wing of the President’s home.”
In 1930, the Massey family sold Ash Lawn to philanthropist Jay Winston Johns, who opened the house for public tours. The photogenic Massey house appeared on advertising brochures for Ash Lawn during the Johns period, and Monroe-focused tours led visitors through the Massey house front door until 2012. While there was never any real confusion that Monroe had lived in the 1870s Massey house, which is an easily recognizable architectural example of its era, there was ambiguity in the public understanding of the site and its relationship to Monroe. It is not clear whether this started in the late 1800s as an intentional deception to draw the site’s standing structures closer to Monroe’s legacy or whether the lack of records created a historic void. By the mid-twentieth century, it had been forgotten that an entirely separate main Monroe house had existed.
Research and Interpretation of the Property
Johns bequeathed Ash Lawn to the College of William and Mary in 1974 to be operated as “a historic shrine for the education of the general public.” Due to lingering questions about the site’s presidential history, William and Mary commissioned University of Virginia professor and Monroe biographer Harry Ammon to examine the documentary record to verify Monroe’s ownership of and residency at Highland. Ammon’s work validated Monroe’s ownership of the property and his presence there throughout the early 1800s.
A major architectural study by Milton Grigg commissioned by William and Mary in 1975 wrongly concluded that the earlier portion of the evolved Ash Lawn house belonged to the partially destroyed house Monroe had built in 1799, solidifying the century-old misunderstanding. In spite of both these research endorsements, doubts remained about the house’s association with Monroe, especially given the modest core of the evolved structure. Critics pointed out that the small house would have been inappropriate for a statesman returning from France with his newly acquired Louis XVI furniture.
William and Mary’s research continued in 1975 with archaeological excavations in and around the foundations of the Massey House. That work failed to find the remnants of the original Monroe house, which should have been discoverable below the surface adjacent to the supposed wing. The negative evidence was not sufficient to challenge the established misunderstanding, so the longstanding interpretation of the building as a remnant wing of the Monroe main house continued. In the mid-1980s, William and Mary re-introduced Monroe’s name for his home and began using the name Ash Lawn-Highland.
In 2014 a new research campaign was initiated by Highland, spurred by discrepancies between the extant architecture and the documentary record. A 2015 archaeological survey and follow-up excavations revealed a well-preserved stone foundation just below the ground in the colonial revival boxwood garden in front of the Massey house. By 2016 enough of the building’s outline had been revealed to demonstrate a correlation with the surviving insurance plats of Monroe’s main house. As part of the same research, Carl Lounsbury, Willie Graham, and Jeff Klee, then of’s Department of Architectural History, flagged architectural components of the supposed Monroe wing that were inconsistent with the wing of a circa-1800 house. They suggested the details indicated a later, free-standing building, and recommended performing dendrochronology, or tree-ring dating, on beams from the structure that had the outer, bark edge intact. Dendrochronology definitively dated the original two rooms of the standing house as the 1818 presidential guesthouse. As a result, in 2016 a new interpretation of Monroe’s Highland was introduced into the historical record, and William and Mary resumed calling the property Highland. For public visitation, it is known as James Monroe’s Highland.
The Enslaved Community at Highland
Monroe maintained Highland as a plantation using enslaved labor from 1799 through 1828. Highland followed the agricultural trajectory of similar plantations, riding the wave of tobacco and then mixed-grain farming. Documents indicate that Monroe enslaved as many as 250 individuals during his lifetime, starting with his inheritance from his father at age sixteen of an enslaved boy named Ralph and unnamed enslaved field hands. Scanty record keeping and the regular relocation of enslaved laborers between plantations and their absences because of house servants, including valets, maids, and cooks.or mortgaging make it challenging to enumerate individuals on Monroe’s various properties. The 1810 U.S. Census records forty-nine men and women over the age of sixteen enslaved at Highland, including field hands, skilled workers such as blacksmiths and carpenters, and
Fates of the Enslaved at Highland
A circa 1900 photograph shows horse-drawn carriages—one of them driven by a Black coachman—in front of the Casa Bianca plantation in Jefferson County, Florida. In 1828, former President James Monroe sold seventeen men, women, and children from his Albemarle County plantation, Highland, to Colonel Joseph White who then owned Casa Bianca. The enslaved sent to Florida served in various ways at Casa Bianca: as field hands, as enslaved domestics, and, in the case of Garrettt Sanders, as a skilled enslaved blacksmith. In 1873, some of the children of the enslaved people who had been exiled from Highland played a critical role in the establishment of the Casa Bianca Missionary Baptist Church in Monticello, Florida.
An advertisement posted in the July 15, 1826, edition of The Central Gazette, a weekly newspaper in Charlottesville, offers a financial reward to anyone who captures an enslaved man named George and an enslaved woman named Phebe, both of whom had escaped from James Madison's Albemarle County plantation, Highland. William Moon wrote the newspaper notice on behalf of James Monroe, the former president of the United States whose term had just expired the year before. The advertisement describes both of the people attempting to free themselves: George was about thirty years old, "strait made, tolerably dark complexion" and was wearing the standard cotton clothing of the enslaved. Moon warns that George "will no doubt change" his clothes in an attempt to evade detection. Phebe, who was about twenty-eight years old, was "clad in domestic clothes," was of average size and "dark complexion." It was believed that the pair were heading to Loudoun County, where Monroe had another plantation and residence which was much grander than Highland. Members of the enslaved community at Highland were frequently transferred to his other plantation, and it is possible that George and Phebe were seeking their own family members. Monroe offered ten dollars for the return of these two enslaved escapees if they were captured in Albemarle County and fifteen dollars if they were apprehended in another county "and secured in any jail so that I get them again."
With Monroe away pursuing his career in politics, the enslaved community at Highland maintained the plantation’s day-to-day operations. Monroe directed a rapid sequence of overseers in supervising the planting of tobacco, corn, wheat, and peach and cherry trees, and operating a gristmill and sawmill, as well as extracting timber from the hillsides, processing wool from Merino sheep, and attempting viticulture. Monroe blamed the overseers for failing to reap desired profits from the Highland acreage. However, as with many Piedmont plantations, profits fell as the agricultural balance shifted from the worn-out tobacco fields of the Upper South to the burgeoning cotton belt of the Lower South. By the time Monroe completed his second term as president, the chief export of the Upper South was enslaved labor. When he sold the final parcels of Highland’s farm lands in 1828, Monroe sold seventeen members of Highland’s enslaved community to Colonel Joseph White, who operated a cotton plantation called Casa Bianca in Jefferson County, Florida. The family groups forcibly relocated to Casa Bianca remained together there beyond the (1861–1865). In addition, an unknown number of enslaved people were sold locally in Albemarle County to cover Monroe’s debts.
There are no originalremaining at Highland. A 1907 photograph depicts a quarters building that appears to be from the 1840s or 1850s and may have been a replacement of an earlier, potentially Monroe-era building in the same location. This building was demolished in the 1920s. It was reconstructed in 1985. The decision to reconstruct a building related to slavery was one of the earliest efforts to interpret slavery through architectural reconstruction among Central Virginia’s historic sites. Another potential slave quarters site, identified through the surface scatter of artifacts and shovel testing, is located in the nearby South Pasture.
Archaeological and landscape research on the property is far from complete. A growing number of descendants of the people enslaved at Highland are collaborating with the museum’s staff to interpret Highland, and effort that began in 2017 and was formalized in 2019 with the establishment of Highland’s Council of Descendant Advisors. The council is advising Highland on the selection of historic narratives and presentations in new exhibitions for interior and exterior spaces.