Bound for New Orleans!

Original Journal of John Halley of His Trips to New Orleans

Performed in the Years 1789 & 1791

By Harry G. Enoch


Who Was John Halley?

John Halley (c1746-1838) was the son of James Halley of Fairfax County, Virginia, whose will named six sons and four daughters. John served as a private in Capt. Nathaniel Hart’s militia company that was ordered to build a fort at the Falls of the Ohio in 1782. According to John Halley’s sworn statement, “[I] first came to Kentucky on 21st March 1780. 1 landed at the Falls from thence I came to Boonesborough and stayed but a short time before I returned to the land office. Became acquainted with the names of upper and lower Howard’s creeks, two mile creek and Otter creek in the spring of 1780.”1

Halley was an energetic entrepreneur on the frontier. In 1787 he and partner John Wilkerson and others drove a herd of cattle to market in Virginia. In 1788 the county of Madison granted Halley “a License to retail all kind of goods wares and merchandise in the Town of Boonsborough.” He was appointed one of the county commissioners and was called upon to “undertake the building of the public Wearhouse at Boonsborough” for the inspection of tobacco and flour. John Halley took a fleet of flatboats to New Orleans the next year, 1789, and again in 1791, keeping a journal on both trips.2

In addition to farming and mercantile interests, Halley was heavily involved in the land business. John and his brothers William and Richard made entries on several tracts of land in 1780, not long after the Kentucky land office opened. That year Lincoln was set off as a county, and John was appointed one of the deputy surveyors. He acquired a number of lots in Boonesborough and nearly 4,000 acres on nearby Otter Creek, where he developed additional business interests. In 1795 he petitioned the county court for permission to build a water gristmill on Otter Creek. Halley received permission to keep an ordinary at his dwelling house in 1818 and had the tavern for at least three years. In 1824, he petitioned the court for additional mills, one described as “a water Griss and Saw Mill on otter Creek” and the other “a water Griss Mill near the mouth of the East fork of Otter Creek.” 3

John Halley and his wife Susan Ann had no children. In 1821, the aging couple made an arrangement with John’s nephew, Samuel Halley, who had recently come out from Fairfax County. Samuel was to receive one half of his uncle’s estate in return for paying $1,000 towards his debts and agreeing to manage all his business and legal affairs (Halley was involved in numerous lawsuits). Samuel was to take possession of John’s land “on the left hand side of the road leading from Richmond down otter creek by Lindseys to Stevens ferry.” He may not have given Samuel enough authority over his affairs, since in a second agreement signed in 1829, John stated that he had suffered “great embarisment and from age and infirmity incable of managing his concerns.” This time Samuel was given an irrevocable power of attorney that allowed him to sell any of John’s assets except “the land and houses on the east side of the road leading to Stevens ferry” and “such servants [slaves] as may be necessary for their comfort.” In 1829, John Halley still listed his address as the “Town of Boonesborough.”4

Family tradition credits Halley with a number of unique accomplishments, such as planting the first orchard in Kentucky, building the first stone house at Boonesborough, the first store at Boonesborough, building the first tobacco barn, and shipping the first tobacco to England. Tobacco has been grown on John Halley’s bottomland near the river from the 1780s to the present. His stone house stood on the west side of KY 388, nearly opposite the Boonesborough State Park entrance. A frame house, built by his nephew Samuel, stood next to it (burned sometime between 1968 and 1972). The tobacco warehouse was just south of the Halley home.

John Halley died in 1838 and was buried in the family cemetery near his home site. His gravestone presently stands by the park fence on the right side of the main entrance. The home and warehouse sites lie under the overflow parking lot on the west side of KY 388.5

Kentucky and the Mississippi River

As soon as early Kentuckians were able to produce a surplus from their farms and small industries, they had to begin looking beyond their borders for markets. Goods could not be profitably carried over the mountains to eastern cities; as Dr. Thomas Clark wrote of this period, “not one of the farm products of Clark County could pay its transportation costs overland, not even whiskey.” Westerners were counting on using the Ohio-Mississippi waterway as an economical shipping route to New Orleans. At the close of the Revolutionary War, the Spanish were in control of the city as well as the lower Mississippi. Spain essentially shut down river traffic while negotiating a treaty with the newly formed United States. Then James Wilkinson, the famous scoundrel and intriguer, broke the barrier. Wilkinson shipped a flatboat load of tobacco, hams and butter from Frankfort to New Orleans in 1787, and while there entered into a secret alliance with Spain. His triumphant return to Kentucky spurred a furious race to get into the business of “trading down the river.” Wilkinson arranged for a second, larger venture in the spring of 1789, but by then a number of market-hungry entrepreneurs had decided to make the trip on their own. With perhaps slight exaggeration, a gentleman wrote from New Orleans in April of that year, “the Mississippi has been covered with fleets of boats from Cumberland, Kentucke, &c. floating down great quantities of provision, flour, plank, &c.” John Halley’s voyage the same year was part of that early movement.6

The Kentucky River provided access points for products of the Bluegrass region and a link to the Ohio-Mississippi route to New Orleans. Previously viewed only as a barrier to land transportation, the river soon was dotted with warehouses for inspection and storage of tobacco, flour and other products, as well as boatyards for constructing flatboats. Madison County records indicate that the Boonesborough warehouse was established in 1788. In 1792 the Kentucky General Assembly established three warehouses for Clark County one at the mouth of Boone Creek (Eli Cleveland’s), one opposite Boonesborough (William Bush’s) and one at the mouth of Lower Howard’s Creek (John Holder’s).7 Inspectors were appointed by the Governor. They were required to check each barrel of flour and hogshead of tobacco accepted by the warehouse in order to ensure the quality of products exported from Kentucky. Warehouses were typically located near shipping points on the Kentucky River. John Holder operated a boatyard near his warehouse, one of the first in the state-the first according to Francis F. Jackson:

The first boat built in Kentucky was at Holder’s landing, now Comb’s ferry…. William Harris was the foreman in building it. Built in 1788. Thompson and McCroskey (Shane’s note: for them?) Both Scotchmen… . The second set of boats were built for General Wilkinson. Harris the superintendent.8

Holder’s boatyard turned out numerous flatboats for the New Orleans trade. These boats followed a similar design, of which the one below was typical:

[S]pecifications called for gunwales “fifty feet long and six inches square, the bottom planks two inches thick, twelve boards to be put across the boat, the side planks to be one and one-half inches thick. The stanchions or studs to be three by six, five feet high and five to a side. The boats to be finished in a workman-ship-like manner, to be pinned with seasoned white oak pins and bored, and the sides to be five feet high and the whole to be of oak timber.” This was the structural description of the “Kentucky boat.” A stout cabin, a pair of ornamental deer horns, a pair of side sweeps, and a long steering oar topped off the equipment.9

New Orleans, Natchez and other ports would remain important markets for Kentucky goods and produce until the coming of the railroads in the mid 1800s.

Halley’s Journals

Halley’s journals of his trips to New Orleans are noteworthy documents from several perspectives. Not only does he provide insightful accounts of what would become one of Kentucky’s major early industries-shipping goods and produce to the port of New Orleans-but he does so almost at the birth of that industry, just two years after Gen. Wilkinson’s inaugural voyage in 1787. Halley was a keen observer, and his record includes a wealth of detail on a broad range subjects. On both voyages there was much concern about the threat of “ingeons,” and Halley comments on his encounters with Native Americans. He describes each visit with Spanish officials and relates something of the customs and manners as he saw them. Halley must have gotten along well with everyone he met, as all seemed to like him. He wrote after every encounter that he was “treated with a great deal of complisance.” He tells of capturing an army deserter, shooting the rapids at the Falls of Ohio (Louisville), getting stuck on a sandbar, breaking his steering oar, almost losing one of the men in a pile of driftwood, etc. He also comments on hunting and fishing along the way, local flora and fauna, weather and river conditions, settlements, and notable landmarks.

The journal of the first voyage in 1789 begins on May 2 at the mouth of the Ohio and ends at New Orleans on June 2. There are descriptions of visits to New Madrid, Ozark (Post Arkansas), and Natchez. Halley mentions “boats” in the plural but does not say how may vessels were in the little fleet. He does not describe the cargo they were carrying, with the exception of some “bacon hams,” nor does he name the crew. He mentions a few of the men in his party: Maj. John Williams (who functioned as a guide for the trip), Wilkerson (who may have been pilot for the boat named the Merow), Capt. Paulin, Mr. Hoy and John Ahearn.

Halley provides more detail about the 1791 trip. They left Boonesborough on April 27 and arrived in New Orleans on June 8. He started with two boats, stopping at warehouses on the Kentucky River to pick up 80,000 pounds of tobacco, and then caught up with two of his other boats at Louisville. Halley reported that the four boats carried 159,000 pounds of tobacco, plus about 2,000 pounds of bacon and lard and 2,000 pounds of flour. The boats were piloted by Halley, Sharp, Mr. Wilkerson and Capt. Blincoe (or Briscoe). Halley describes stops at Louisville, New Madrid, Walnut Hills (Vicksburg), Natchez, David Tanner’s place, and Baton Rouge. Halley stayed in New Orleans until starting home on September 15. He left his nephew, William Wilkerson, behind to collect $377. Wilkerson was directed to take payment in cattle, which he was then to sell and split the profits with Halley.

Halley did not say how he came out financially on the ventures, but we might infer that he did very well. At that time, tobacco was selling in New Orleans for ten dollars a hundredweight, which would have produced gross revenues of $15,900. Even after paying a Spanish import duty of twenty-five percent, there would have been considerable room for profit. 10

Halley’s bold journeys made a lasting impression in his central Kentucky neighborhood. In an interview with Rev. John Dabney Shane, one of the aging pioneers was telling about trade on the river and recalled that

John Halley was the first man that ever took a boat (a flat) down the Kentucky River. This in 1790 or 1791.11

We cannot say if his recollection was uncertain or if he meant to say the first boat from Boonesborough. What impresses us is that he still recalled the event nearly sixty years after it happened.

Other Accounts of Flatboat Trips to New Orleans

Several other travelers left accounts of their voyages down the Ohio and Mississippi Rivers. Two of these-John Pope’s and Samuel Forman’s occurred very close to the time of John Halley’s trip. William Calk’s and John Stuart’s trips were a little later, 1804 and 1806, respectively. Calk was a one-time neighbor of John Halley at Boonesborough; Stuart lived in the northeastern section of Clark County.

John Pope of Richmond, Virginia, kept a colorful account of his river journey from Pittsburgh to New Orleans. After a two month sojourn in Louisville, he departed on March 4, 1791 and reached New Orleans on April 4. Pope mentions numerous encounters with boats going up and down the river, including a fleet of Gen. James Wilkinson’s boats bound for New Orleans. Many of his colorful observations parallel those of John Halley and are included here in the footnotes to Halley’s journal. 12

Samuel Forman (1765-1862) left a memoir of his trip down the Ohio and Mississippi. He made the journey in two stages, first, accompanying his uncle from Pittsburgh to Louisville in January 1790 and, second, leaving Louisville in May on a fleet of tobacco boats and debarking at Natchez. His brief account recalls only a few happenings along the way. He gives a lengthy description of their visit to New Madrid and an encounter with a group of friendly Indians.13

William Calk (1740-1823) kept a journal of his voyage from Boonesborough to New Orleans in 1804. It is informative but not nearly so colorful as his account of the trip from Virginia out to Kentucky in 1775. Calk was making his “first adventer on speculation with a Boat loaded with corn tobacco bacon & laird.” He notes the dates many landmarks were passed but includes little detail of events or things he saw on the way. One interesting feature is his description of the journey back to Kentucky, which took forty-four days. His route was by way of Lake Pontchartrain, Natchez, Chickasaw town, Tennessee River, Duck River, Nashville, Green River, Danville, Boonesborough and finally home to Mt. Sterling. The road from Natchez to Nashville was the famed Natchez Trace, formally established in 1803.14

John G. Stuart (1783-1853) was born in Virginia, the son of James Stuart who died in Clark County in 1835. John Stuart is listed as a farmer in the 1850 census, and he is buried in the Stuart Cemetery on Wades Mill Road. Stuart went along as a hand on the flatboat of G. Halley, whom we learn was the nephew of John Halley himself. On February 22, 1806, Stuart joined the boat at Cleveland’s Landing at the mouth of Boone Creek. He spent the first 52 days waiting for the river to rise. The scope of the annual launch on the “spring tides” may be judged from his statement, “There are said to be at this time about 100 Boats lying in the Kentucky waiting for water to carry them out.” He made the following observation on the boatmen: “This evening there came down a boat commanded by John Sublitt for Hart & Co. The crew are a specimen of what I may expect to see in my voyage-drinking, swearing & kicking.” They finally set off on April 16. Within two days the river had risen over 50 feet. 15

It is appropriate to mention in this section Zadok Cramer’s The Navigator, which was first published in 1801 and went through many editions. Sold for a dollar a copy, this book filled the need for a dependable guide for safely navigating the uncharted waters of the Ohio and Mississippi. In a time of westward expansion, Cramer’s book was used by people descending the river in search of new homes. He described the rivers’ courses in great detail, warned readers of dangers and alerted them to impressive sights. In the process, Cramer documented the river and its landmarks for future generations. His work is cited here frequently, in the footnotes to Halley’s Journals. 16

Transcribing the Journals

Several sources have reported that the original journals were donated to the University of Kentucky Library by Halley family descendants. The journals cannot be found at the UK Library nor is there any record of their receiving them. UK Special Collections does have a bound photostatic copy of the original journal donated by Judge Samuel M. Wilson. The transcription was made from this copy. In trying to make the journal more accessible to modern readers, several conventions were followed. Paragraphing has been added along with periods at the end of sentences and commas where essential for clarity. However, capitalization and spelling follow the original. John Halley was not consistent in his spelling but he always gave a pretty close phonetic rendering. All of the people and places are recognizable, even though there must have been instances where he only heard the names spoken and never saw them spelled out. An effort has been made to identify the many people and places mentioned in Halley’s journals (see footnotes to the text).


1John Halley’s deposition in Nathaniel Hart’s heirs vs Samuel South and William Calk, 1806, in Charles S. Staples, “History in Circuit Court Records, Fayette County,” Register of the Kentucky Historical Society (1933) 31:316; Fairfax County (Virginia) Will Book F:134; Margery H. Harding, George Rogers Clark and His Men, Military Records, 1778-1784 (Frankfort, 1981), p. 131.

Halley gave additional information about his first visit to Kentucky in another deposition, dated 1813, in the case of John Chiles vs William Halley’s heirs, Clark County Circuit Court, 1808:

In the year of 1780 1 landed at the Falls of the Ohio River, and came to Boonesborough. I met Enoch Smith, Moses Thomas and others who wanted to explore the country. I was told I could go with him, but could not mark out what he had already viewed out and marked for The Difficult Company, some of whom lived on Difficult River in Loudoun County, Virginia. We went to the waters of Stoner and Hingston, and stayed a few days. We killed our loads of meat and returned…. This was before the land offices were open for Treasury Warrants in Kentucky. In May 1780 1 went with Enoch Smith and others to the land office and laid in land warrants and drew lots for priority of entering.

James Halley’s 1792 will listed the following children: William Halley, James Halley Jr., John Halley, Richard Halley, Francis Halley, Henry Simpson Halley, Sarah Haney (married lst, William Wilkerson and, 2nd, William Haney), Sybill Peake (married Jesse Peake), Mary Crump (married Richard Crump) and Susanna Said (married William Said). John’s brother Francis and sister Sybill died in Madison County; brother Richard lived in Clark County.

The name was pronounced “holly” or “hawley” and as a consequence was often spelled “Holley.” There was another John Halley in Kentucky in early times. John Halley (c1726-1802) of Bedford County, Virginia was at Braddock’s Defeat and later came to Boonesborough. In 1778 while out with Daniel Boone’s salt makers at the Lower Blue Licks, he was one of the men kidnapped by the Shawnee and taken to Ohio. He was rescued in 1782 and returned to Bedford County. He claimed 400 acres of Kentucky land on a settlement certificate. His tract on Glenn Creek in Woodford County was surveyed in 1791 and patented in 1795. John Halley Jr., who settled and died in Montgomery County, sold the tract for his father. Lyman C. Draper MSS 12 CC 200; Ann H. Mack, “Hawley/Halley in Seventeenth Century Virginia,” Virginia Genealogist (1985) 29(l):21.

2 Rev. John D. Shane interview with William Sudduth, Lyman C. Draper MSS 14 U 114; Madison County Order Book A:97, 99, 125, D:438, E:136.

3 Fayette County Entries A:170, 171, 271; Lincoln County Order Book 1:129; Joan E. Brookes-Smith, Master Index, Virginia Surveys and Grants, 1774-1791 (Frankfort, 1976); Joan E. Brookes-Smith, Index for Old Kentucky Surveys & Grants (Frankfort, 1975); Madison County Deed Book A: 145; Madison County Order Book B:288, D:438, E:136, 336.

In his interview with Rev. John D. Shane (1840s), William Clinkenbeard mentioned the mills and recalled that Halley owned with John Wilkerson: “Wilkerson & John Holley had a mill on Otter Creek, just to the other side of Boonesborough.” Lyman C. Draper MSS 1 1 CC 65.

Thomas Hinde’s map (c1820s-1830s) shows “Holley’s Mills” on Otter Creek and “Holley’s House” nearby on the Boonesborough-Richmond Turnpike. The house may have been for the miller and owned by Halley. Nancy O’Malley, Searching for Boonesborough (Lexington, 1989), Appendix B.4 Madison County Deed Book R: 124; S:226.

s George N. MacKenzie, Colonial Families of the United States, Vol. III (Boston, 1907), p. 303; Charles Kerr, editor, History of Kentucky, Vol. lI (Chicago and New York, 1922), p. 1171; William Eaton, “John Halley Bought Ferry To Promote Boonesborough Agricultural Potential,” Winchester Sun, June 17, 1965; Nancy O’Malley, Searching for Boonesborough (Lexington, 1989), pp. 32, 65-68, 73.

Among the other graves identified in the cemetery, one was John Halley’s sister’s, “Sibll Peak, died November 1823, aged 80 years,” the wife of Jesse Peake. Kathy Vockery, Cemetery Records of Madison County, Vol. I (n.p., n.d.).

Photographs of John Halley’s stone house and Samuel Halley’s frame house may be seen in the “Halley family papers, 1740-1865,” Special Collections, M. L King Library, University of Kentucky, Lexington.

6 Thomas D. Clark, Clark County, Kentucky, A History (Winchester, 1996), p. 103; Mary Verhoeff, The Kentucky River Navigation (Louisville, 1917), pp. 42-81.

7 Madison County Order Book A:97; Mary Verhoeff, The Kentucky River Navigation (Louisville; 1917), pp. 231-232.

8 Rev. John D. Shane interview with Francis F. Jackson, Lyman C. Draper MSS 15 CC 10. The first flatboats built in Kentucky were constructed prior to 1788. Josiah Jackson and his son Francis produced tar used to caulk flatboats, including Wilkinson’s.

9Thomas D. Clark, The Kentucky (Lexington, 1969), p. 69.

10 Mary Verhoeff, The Kentucky River Navigation (Louisville, 1917), p. 57.

11 Rev. John D. Shane interview with Benjamin Allen, Lyman C. Draper MSS 11 CC 79, transcribed by Lucien Beckner in Filson Club History Quarterly (1931) 5:63.

12 John Pope, A Tour through the Southern and Western Territories of the United States of North-America, etc. (Richmond, Virginia, 1792).

13 Samuel Forman, Narrative of a Journey Down the Ohio and Mississippi in 1789-90 (Cincinnati, 1888).

14 William Calk, “William Calk’s Trip to New Orleans, 1804,” The William Calk Collection, Kentucky Historical Society, Frankfort.

15John G. Stuart, “A Journal, Remarks or Observations in a Voyage down the Kentucky, Ohio, Mississippi Rivers &c,” Register of the Kentucky Historical Society (1952) 50:5; Clark County Will Book 8:330; U.S. Census, Clark County, Kentucky, 1850; Kathryn Owen, Old Graveyards of Clark County, Kentucky (New Orleans, 1975), p. 122.

16Zadok Cramer, The Navigator, 8th edition (Pittsburgh, 1814).