The Routh family were early settlers of the Natchez District of British West Florida who managed to preserve and extend their wealth continuously through the American territorial period and into the period of Mississippi statehood, up until the American Civil War, an unusual feat of financial endurance otherwise only accomplished by the Surgets, Bingamans and the Minors. By the time of the 1860 U.S. federal census, the heirs of Jeremiah Routh, who had accumulated and monetized large land grants from the British and Spanish, collectively held one of the largest slaveholdings in the U.S. South, including at least 1,295 people enslaved in Tensas Parish, Louisiana.

These 1,295 people, legally held by four members of the Routh family, collectively produced "nearly 5,000 bales of cotton" in 1859, placing them in the top tier of cotton growers nationwide, which at that time was the single-most valuable agricultural product of the United States.

The family owned a number of grand homes around Natchez, Adams County, Mississippi, and before the war, the family owned at least a dozen plantations bordering Lake St. Joseph, an oxbow lake in Tensas Parish (roughly opposite the Claiborne and Jefferson counties of Mississippi, immediately north of Natchez), including properties of Routh grandsons-in-law Samuel Worthington Dorsey of Elk Ridge plantation and Haller Nutt of Winter Quarters and Evergreen Place plantations. In addition to Winter Quarters, the Routh fortune built the historic antebellum mansions Dunleith and Longwood.

Jeremiah Routh

Jeremiah Routh (1740–1791) was from North Carolina and died in the Natchez District in 1791. According to one account he was granted 500 acres near Boyd's Creek in 1776. Other early settlers scattered through the countryside at that time included Anthony Hutchins, Richard Ellis and John Ellis, Bernard Lintot, William Marshall, John Turner, William Vousdan, and the sons of Rev. Jedediah Smith (Calvin Smith, Philander Smith), whose father had died within a week of landing in the Natchez.

Edith Wyatt Moore, a 20th-century Natchez booster and untrained local historian, retold a colorful version of the true story of Jeremiah Routh having hauled planed, finished lumber down the Mississippi River to Natchez via flatboat. Insufficiently moored at Natchez-under-the-Hill, the cargo-laden boat drifted away or was stolen by a "rascal" named John Olivary. Many years after the fact, and after the death of Jeremiah Routh, the Routh heirs received a court judgment compensating them for his lost lumber.

Jeremiah Routh Sr. and Margaret Matilda Routh had at least six children: Job Routh, Jeremiah Routh II, Mary Matilda Routh, Zaccheus Routh, Francis Routh, and Elijah Routh. There was a land grant made to one Zaccheus Routh in June 1779. The 1792 Spanish census of the Natchez District listed Elias Routh, Jeremias Routh, Job Routh, and Margaret Routh of Villa Gayoso, and Juan Routh (John Routh) of Bayou Pierre. "Routh's Old Place" was described in 1809 as being 550 acres on the north fork of Cole's Creek, three miles from Old Greenville and five or six miles from the Mississippi River.

Job Routh

Job Routh (1762–1834) was born around 1762 in Mecklenburg County, North Carolina. When he was eight years old, he reportedly almost drowned in the Potomac River and was saved by a family dog. In honor of this, Routh commissioned a cast iron sculpture of a Newfoundland dog for the family cemetery.

Routh came to Natchez from Kentucky in March of 1790. On September 7, 1792, he received a land grant of "a thousand arpents" at Natchez from Francisco Luis Héctor de Carondelet. The grant "covered a vast area, comprising the lands of some of our most noted mansions, such as Dunleith (formerly Routhlands) Richmond, Lanfollan, Arlington, Ashburn, Kenilworth, and Oakland, now known as Routhlands. Antedating these mansions by fully fifty years was the first Routhland (Dunleith) and Hope Villa. Job Routh became one of our earliest nabobs and not only gave his children lordly estates, but willed them slaves and cattle."

Job Routh became one of the largest landowners and slaveholders in the antebellum South. An early settler in Concordia Parish testified in a lawsuit over a ferry franchise that around 1801 there was a ferry between Natchez and the Spanish colonial "Post of Concordia" (later Vidalia), "used principally for crossing stock by Job and Jeremiah Routh, but I think it was for their own private use." Job Routh was granted a tract in what is now Tensas Parish in 1803, in vicinity of three oxbow lakes that were former bends in the Mississippi River: Lake Bruin, Lake St. Joseph, and Yucatan Lake. According to a 20th-century account, Job Routh also "obtained a large grant of land across the River in Louisiana near Lake St. Joseph, and there he and his children cultivated 20,000 acres with 5,000 slaves as labor. Part of the year they lived in their town houses in Natchez, and the rest of the time on the plantations on Lake St. Joseph. There were fifteen homesteads belonging to the Routh family in Tensas Parish, Louisiana, where life was one long series of balls, dinners, picnics, horse races, and boat races. Just prior to the outbreak of the War between the States John Routh, a son of Job Routh, made a cotton crop of 8,840 bales in one year." Another account has it that his Louisiana property stretched from Newellton to Hard Times plantation.

In the 1790s, he constructed a mansion called Routhland. This mansion was described as one of "Natchez's grander structures, with two stories and galleries on at least two sides. The setting was a 1700-acre estate near the southern edge of the city." The first recorded burial at Routh Cemetery adjacent to Dunleith on Homochitto Street in Natchez dates to 1818; there are a total of 46 known burials in the cemetery, including three formerly enslaved people.

In 1805, Routh established a residence at a place he called Winter Quarters in Tensas Parish, Louisiana. The plantation was so-named because the residents lived elsewhere during most of the year but came south for the winter. The house at Winter Quarters was originally a three-room hunting retreat built out of logs felled and hand-hewn on site by the enslaved community on the property, and eventually expanded to 19 rooms, five of which were added in the 1820s by the Ogdens.

Job Routh appears as a local man of substantial wealth on the 1807–1812 tax rolls for Adams County, Mississippi Territory, alongside James Wilkins, Samuel Postlethwaite, Abijah Hunt, Alexander Moore, Lyman Harding, Charles Green, John Perkins, John Carmichael, Frederick Seip, Winthrop Sargent, Christopher Miller, Adam Bingaman, Stephen Minor, John Girault, William Vousdan, Jonathan Thompson, and Lewis Evans. In 1816 Job and John Routh were advertising a $30 reward for three enslaved men recently imported from Kentucky; Mike, Isaac, and Sandy ("who speaks good English for an African") had escaped from the Routh property at Lake St. Joseph.

Routh died on December 12, 1834, and was buried in the family cemetery near the present-day site of Dunleith. His executors were his son John Routh, his sons-in-law Austin and Archibald Williams, and his friend Jacob Eiler. He prohibited his daughter Sarah Jane Routh Walker from being named an executrix, and ordered that "'Old Sookey is to choose which child she shall belong to and her husband is also to go to that child whom Sookey chooses,' while Sarah Jane Walker's share of the property was entailed for her children, the trustees or executors being told to allow her the rents or income only from her share."

Heirs Job Routh married Ann Madeline Miller, a sister of fellow early settler Christopher Miller. The couple had nine children: Anna, Caroline Matilda, Elizabeth, Francis Routh, Jane, John, Mary, Sarah, and Stephen.

Mary Routh, who married second the banker Charles G. Dahlgren, inherited the Natchez Routhland. This Routhlands house was struck by lightning and burned down in 1855. Charles and Mary were vacationing, in Saratoga, New York, at the time of the fire, but Dahlgren blamed his wife, writing, "'[The house] was struck by lightning and destroyed, in consequence of my wife desiring terra cotta chimney tops placed, which were elevated above the surrounding china trees, and so affording an object for the electric fluid.'...The family returned to Mississippi to find their home a pile of bricks and ashes. Fifteen stuccoed steps marked the site of the main entrance, and a variety of interesting Gothic outbuildings had survived as well. A two-story brick barn and stable, a garage and kennel with a hexagonal columbary, a greenhouse, and a servants' lodge all bear witness to what must have been a sensational home." The Dahlgrens constructed the building now known as Dunleith in its place. Mary Routh Ellis Dahlgren lived there only two years before she died of heart disease in 1858; Dahlgren rapidly remarried and built Llangollen, which burned in 1932.

John Routh m. Nancy Smith Matilda Routh m. Dr. Allen T. Bowie Calvin Routh m. Ann Skillman Elizabeth Routh m. Archibald Williams Caroline Routh m. Austin Williams, they built Ashburn house, which burned in 1873 Their daughter, Jeremiah Routh's granddaughter, Julia Augusta Williams married Natchez planter Haller Nutt, and inherited Winter Quarters. Winter Quarters was the only plantation house in the vicinity of Lake Saint Joseph to survive the American Civil War. According to an account of the war passing over the lakeside settlement, "Haller Nutt claimed that between burnings by Confederates and burnings by Federals he had lost more than 4,500 bales of cotton in the war. If this is true, at 1863 cotton prices it was a loss worth in U. S. gold." Julia Nutt lived at the unfinished Longwood ("Nutt's Folly") on the Mississippi side of the river after her husband's death in 1864. Sarah Routh m. Col. Walker Eliza Routh m. William Cochrane Frank Routh m. Mary Lane Ann M. Routh m1. Lane, m2. Dr. Elias Ogden, "born in Morris Co., N. J., and studied medicine with his uncle Dr. Isaac Ogden...after which he removed to Port Gibson, Miss., where he built up a lucrative practice. While in Port Gibson, he married Mrs. Ann M. Lane, nee Routh, who owned one of the largest and finest plantations in that section of the country, lying in the suburbs of Natchez, Miss. Here he built an elegant residence called Kenilworth, retired from the active practice of his profession, and devoted himself to the care of the extensive estate belonging to his wife." Dr. Ogden bought the defaulted Routhlands from the sheriff in 1842, and sold it back to his mother-in-law.

Mary Routh m1. Thomas G. P. Ellis (son of John Ellis), m2. Charles Dahlgren – Mary was the youngest; she married Ellis of Wilkinson County in May 1828. Upon Job Routh's death, the Ellises sold Hope Farm (also known as Hope Villa) to Eli Montgomery, whose family occupied it for the next 90 years. Job Routh's wife was Eli Montgomery's aunt, through the Millers. Eli Montgomery was kin to the local politician Alexander Montgomery and lawyer Alexander Montgomery, the latter of whom was partners for a time with S.S. Boyd, who was partners for a time with Rice C. Ballard, who had been partners for a time with Isaac Franklin. Sarah Ellis (1829–1879) m. Samuel Worthington Dorsey; she was a novelist and patron of post-war Jefferson Davis

Jeremiah Routh II Jeremiah Routh Jr. (1763–1815) was the youngest of Jeremiah Routh Sr.'s four children. Natchez at the turn of the 19th century was a barely governed borderland, and "ads for the sale of slaves insinuated that African American women might be used as prostitutes. Jeremiah Routh placed this cryptic ad in one local newspaper in 1804, 'for sale or hire. Eleven young Negro girls, all capable of business...'"