A Boyhood on the Kentucky Frontier

© 1997 Robert Perry, Ph.D.

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Descendants of Andrew Jackson May

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If large families are a sign of marital bliss, the period from 1809 to 1833 was a happy one for Samuel May and his wife Catherine. Records show that during those years, she bore him six sons and eight daughters. Nine of these children were born at the May House in Prestonsburg, Kentucky, which in those days was the hub of his beautiful, four-hundred-acre farm. Like most frontiersmen, Samuel was a loyal Democrat and a strong supporter of Andrew Jackson, the champion of backwoods causes on Capitol Hill. Accordingly, when Catherine bore him his fourth son on January 28th, 1829, he named the boy after his hero, who was just beginning his first term as president. In thirty-two years the boy would become Colonel Andrew Jackson May, the man Henry Scalf called "The Plumed Knight of the Southern Cause in the Big Sandy Valley."

What was it like to grow up at the May Farm during the 1830s? Since Prestonsburg didn't have a newspaper during those years, and most of Jack's papers have been lost, we know very little about his childhood. However, we do have the diary of Reverend William B. Landrum, a Methodist circuit-rider on the Big Sandy during the 1828-1879 period. In the Summer of 1839, he visited the May Farm and performed a wedding ceremony:

On Sunday, the 28th of July, I preached in Louisa, and after dining at J. M. Rice's, I went in company with several persons to Mill Creek, and preached for the first time in the State of Virginia. I staid all night at F. Moore's. Monday, the 29th, I rode up to Paintsville and staid all night at a Mr. Hutton's, and next day I went to Samuel May's [farm] near Prestonsburg and performed the rite of matrimony between Dr. Perez S. Randall and Mahala May, in the presence of a great many persons, and we had a spendid dinner.

This passage supports the tradition that the May House was the center of Floyd County's social life during the early days, and it also shows that Samuel May was a generous host. Using Tress May Francis' genealogy, we can reconstruct the wedding party. Samuel's immediate family, including his mother Sarah and his wife Catherine, probably filled the front pew, and ten-year-old Jack May probably fidgeted during the ceremony. Samuel's brother Thomas probably came down from Robinson Creek, bringing his wife Dorcas and their twelve children. Samuel's sister Mary and her husband John Hamilton probably came from their farm in Morgan County, bringing their seven children. It is less likely, however, that Samuel's brother John and his family attended the wedding, for they would have had to travel all the way from Shelby County, Illinois.

Perez S. Randall, Jack's new brother-in-law, was a doctor who had moved to Prestonsburg the previous year. In his mid-thirties, he was a widower and a native of Maine. His young bride was a real catch. Jack May's daughter Mary, who knew Mahala in her later years, considered her to be "One of the most interesting and handsome women I have ever known. She dressed in soft black silks and cream lace, had beautiful silver hair, and looked a perfect queen." After their honeymoon, the Randalls settled in Maysville. When the war came, Randall enlisted in the Union Army and served for three years as a surgeon with the 5th Virginia Infantry, U.S.A. He also served with the 14th Kentucky Mounted Infantry, U.S.A., whose headquarters was at Louisa, Kentucky.

Here is an old tintype of Perez and Mahala discovered by Tress May Francis, the first genealogist of the May Family.

What were Jack May's boyhood amusements? In later years he was an expert horseman, so it's a good bet that he spent part of his boyhood riding horses around his father's racetrack. It was located in the meadow below the May House, on land now occupied by the Highland Plaza Shopping Center. Family tradition says that Samuel and his sons loved to race horses, and that their races attracted large crowds. A similar race track was located at the Cassiday Farm near West Liberty. Writing for the Morgan County Messenger in 1896, William H. Hampton recalled that in the 1830s, every Saturday afternoon, "young blades as well as solid businessmen" would congregate at the Cassiday Farm to race their horses and socialize. When the races were finished, the crowd would retire to the Morgan County courthouse for an evening of "merry times."

Samuel May's horse races were probably match races, fairly simple affairs in which two horsemen competed for a purse collected from the crowd. Family tradition says that a ticket booth was located at the northeast corner of the house. One of the local men who attended these races--or knew those who did--was Lewis Mayo of Van Lear, "a teacher of great learning and ability." In September, 1840, Lewis composed a letter to his uncle, William James Mayo, who was then living in Paris, Illinois, and brought him up-do-date on the local gossip:

Oat crops were good, wheat indifferent, corn pretty good. Much political agitation. Some of us hope that Van Buren will be re-elected. About Prestonsburg the people talk more about horse racing lately than about politics. Mr. May, in his fine bottom, recently had a one-mile race path trimmed out. I suppose a few days after the death of one of his brothers, he, by a race at that place, won $100. I suppose several will be run for next Thursday. I have agreed to teach a school in this neighborhood for four months, before the last of March.

Jack's chief boyhood amusement was probably hunting. When Pikeville merchant John Dils traveled up the Big Sandy in 1836, he found a hunter's paradise. "Hunting was the principal occupation of both young and old. In the season for killing game, a man without a gun was out of an occupation, unless he was a merchant or a preacher." Edward O. Guerrant, who served with Jack under General Humphrey Marshall during the Civil War, notes in his diary that Jack's speech was salted with expressions associated with hunting. He would say things like "Tomorrow I'm going to ride over to Campton and bag myself some bushwhackers."

Although Jack grew up on Kentucky's Last Frontier, it would be a mistake to assume that he wasn't well-educated. His letters reveal not only that he could write, but that he could write well. This fact and the fact that his father was well-to-do suggest that he received his education at Prestonsburg Academy, a private school located only a mile from the May Farm. Established in 1820, the academy was a two-story brick building located on land now occupied by Old Prestonsburg High School, which today houses the offices of the Floyd County Public Schools.

Henry Scalf claims that the first headmaster of the academy was the previously mentioned Lewis Mayo, but this is hard to reconcile with the fact that Mayo didn't arrive in the region until 1837. The hard times which followed the Panic of 1837 probably put the academy out of business, because legislative records show that the building was empty by 1856. During the War Between the States, until it was accidently destroyed by fire, it was used as a barracks by Federal soldiers. The fire probably destroyed all its records. Henry Scalf knew old-timers who could remember playing in the pile of bricks which marked the site of the school.

Jack's childhood was a period of rapid economic development. When the first steamboat ascended the Levisa Fork of the Big Sandy and docked at Prestonsburg on May 20th, 1837, Jack was probably in the crowd which cheered its arrival. On the following day, after its "spring importations" had been unloaded, it carried a "pleasure party" of local dignitaries even farther up the river. The newspaper reporter covering this event noted that "coal of the finest quality" was visible in outcroppings along its banks. Here is a photo of the steamboat Cando docked at Prestonsburg in 1891:

In 1841, when Jack was twelve years old, Richard Deering established the first coal mine in Floyd County at Abbott Shoal, on land he had purchased from Jack's father. Although hard times nipped this enterprise in the bud, other mines soon followed. Located at the mouth of Abbott Creek, Abbott Shoal was also the center of the local logging industry, and as a young man Jack probably helped his father buy logs, saw them into lengths, tie them into rafts, and float them down the river to Catlettsburg. In 1849, keeping abreast of the new technology, Samuel May erected a steam-powered saw mill and grist mill at the mouth of Abbott Creek.

As the favorite son of Floyd County's leading politician, Jack would have been in the crowd when his father delivered the annual Fourth of July Oration from the balcony above the May House porch. State Senator from 1834 to 1839, Samuel was a tireless promoter of Eastern Kentucky projects, and it was largely due to his efforts that in 1837, the state legislature appropriated $25,000 for the construction of the Mount Sterling--Pound Gap Road. The first state highway in the region, this road ran from Mount Sterling through West Liberty, Hazel Green, Licking Station, Prestonsburg, Laynesville, and Piketon up to Pound Gap, where it linked up with a road constructed by the Commonwealth of Virginia. You can follow the route of the road on this 1834 Map of the Commonwealth of Kentucky. The road is visible in the foreground of this 1891 photograph of the south end of Prestonsburg:

During the years prior to the Civil War, the Pound Gap Road was used to drive livestock raised in the Bluegrass--horses, cattle, and hogs--to markets in Southwestern Virginia and Eastern Tennessee. Since it crossed the Big Sandy at Abbott Shoals, where he operated his grist mill and ferry, Samuel's interest in the road was personal as well as political. He dreamed of the day when his farm would become a livestock feeding station and his brick mansion a prosperous wayside inn.

Unfortunately, Samuel's dream was shattered by the Great Depression of 1837-43, which drove him into near bankruptcy. In 1841 he was forced to sell his saw mill and grist mill to Richard Deering, and in 1842 he was forced to sell his farm, with its stately brick mansion, to his brother Thomas May (1787-1867), a wealthy Pike County farmer and landowner. Thomas subsequently divided the farm and deeded the two halves to his fourth and fifth sons, William James May (1819-1883) and Samuel May (1820-1904), giving William the portion containing the May House. Following this transaction, Senator May moved his family to a smaller house in Prestonsburg, a move that must have been especially embarrassing for thirteen-year-old Jack May.

Like his father, Jack May was a man of exceptional courage, unbending integrity, and driving ambition. He had the bad luck, however, to come of age when his father's business empire was collapsing. Dealt such a hand, it was inevitable that he should dream of recouping the family fortune. When news reached Prestonsburg in 1849 that gold had been discovered in California, it was probably twenty-year-old Jack May, not his father, who first rose to the bait. Whatever the case may be, we know with certainty that when Samuel headed west in 1849, he took Jack with him, and "another young man named White." A photograph of Jack from this period shows a sharp-featured young man with a determined expression and a glorious mane of red hair.

The story of Samuel's Death in the Goldfields has already been told, so I won't repeat it here, except to say that he probably caught pneumonia while standing in a mountain stream panning for gold. His final hours were made more bearable by his son's selfless devotion. When Samuel died in their lonely, wind-swept cabin near Placerville on February 27th, 1851, Jack buried him on their claim and returned to Prestonsburg, where his mother was still living. There he began studying for the law. He was licensed to practice in 1854, and in 1855 he married Matilda Davidson, the daughter of a prosperous Floyd County farmer. By 1860, according to the U. S. Census, Jack was practicing law in West Liberty, a town thirty-five miles west of Prestonsburg in Morgan County.

Most of Jack's letters from this period have been lost, but we do have a letter which he sent to his bride-to-be on January 20th, 1855, several weeks before she accepted his proposal of marriage. The person who discovered the letter is Lida Howard of Prestonsburg, granddaughter of Lida Davidson Spradlin. In the Fall of 1997, Lida and I spent several evenings going through old letters that her mother Margaret had inherited from the Davidson family. Lida Spradlin was a niece of Matilda May and the sister of Nelle Davidson May, Jack May's second wife. How the letter ended up in the possession of Lida Davidson Spradlin is a mystery, but there is no doubt that it is authentic.

The heading of the letter is "Manchester, Clay Co., Ky, Jan. 20th, 1855." Evidently Jack spent a year or two in Clay County before establishing his law practice in West Liberty. The letter is an interesting one, and it provides ample proof that Jack was an educated man familiar with the idioms of Standard English and the courtship rituals of the American Middle Class:

Miss Mary M. Davidson:

Dear Matt: Your exquisite letter reached me today, and although I wrote one a few days ago in answer to yours, yet this would seem to require another one, and one, too, which it affords me a great deal of pleasure to write. Well, Matt, you have come out and spoken like a true woman at last. I know that it was a hard confession for you to make, and doubtless you pondered long ere you could get your own consent to make the avowal. But 'tis made at last and is most heartily responded to by me. You have ere now received my letter, and it is almost unnecessary for me to assure you that my feelings have undergone no change since I last stood in your presence. That I love you you are satisfied. Have I not given you abundant proofs? Methinks so. Well, Matt, I am satisfied that you really love me, and, to tell the truth, I have scarcely ever doubted your affection for me, but never could reconcile your conduct with what I believed to be the sincere sentiments of your heart.

But let us bury all that, and live in the future and not in the past, for I doubt not but that you have suffered nearly or quite as much as myself. It would be useless now to indulge in regrets for that which cannot now be recalled, now that we understand each other. Conscious that we love and are beloved, let that be the common ground on which we can stand, live, and die. You say that their [sic] are none in whom you can confide [text illegible]. I understand by that that your friends or any of them are or will be opposed to our union, or is it simply because you do not confide such matters to anybody? If the first, I should regret it exceedingly for to marry you without the approbation of some of your friends, with whom I have ever been intimately associated. [This] would be goading to my feelings, but I indulge the hope that there is nothing of the sort in the way. If there is, why, it must just get out of the way.

Well, here I am talking away about our marrying, forgetting that it takes two to make a contract, and that you have not yet yielded your consent. But as we love each other, we must marry. So now, dear Matt, I want you to take this matter into serious consideration. You know that life at best is but a span, and although I am unfortunate enough not to be able to present much of this world's goods for your acceptance, (which I regret very much, for your sake alone), yet the way is as open for me as it was for those who have preceded me and successfully climbed the steps of life. With youth, health, and a good profession, may I not indulge the hope that all will yet be well?

Matt, I cannot say just now when I shall be in Floyd. That must depend greatly upon yourself and on the action which you take in this matter. Believe me, dear girl, I am very anxious to see you and will try to come over in the Spring--perhaps in March. Well, now, that's cutting down the five years that I talked to you about when I saw you last, to a mighty small figure. You will have to engage a priest and absolve me for telling that story.

Now Matt, answer this letter, and, as you say, you can confide in me. Make all and any suggestions that present themselves to your mind, relative to the present or the future. You see, I have been very candid with you. May I not hope that you will be equally so with me? Any suggestions which you may make will have due weight with me.

I have been writing all day and my hand is nervous, and considering the fact that I wrote you a few days ago, I will close by assuring you that the happiest moment of my life will be when I can call you mine.

Yours affectionately,

A. J. May

© 1997 Dr. Robert Perry

Dr. Perry has put all of the chapters of his book on-line in a website he maintains in geocities.com. Click below to leave the mayhouse.org site and view the remaining chapters of JACK MAY's WAR.

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For additional information on the home where Col. May was born click HERE.

Maps of towns and counties mentioned in this chapter can be located in Pam Rietsche's wonderful 1895 U.S. Atlas, a very handy tool for on-line historians and genealogists.

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