Appalachian Figures
In the summer of 1815, a boy named Reuben May was born on Robinson Creek in what is now Pike County, Kentucky, into one of the most connected families on the Big Sandy. Later records from Wisconsin and a century’s worth of genealogical work agree on those basic facts: he was born June 23, 1815, in Pike County, son of Thomas Phillips May and Dorcas Patton, and he grew up on his father’s substantial mountain estate.
To understand why that mattered, you have to go back a generation. In a long reminiscence titled “A Sketch of the Big Sandy, Ky.,” written in 1902, Methodist minister M. T. Burris described how the May family came into the valley from eastern Virginia in the 1790s. He remembered an “old man May” who settled on a rich bend of the river above Prestonsburg, building what he called the finest house in the county. Burris then listed the children he knew: Samuel, Thomas, John, Reuben, and Pollard, and noted that Thomas May settled on Robinson Creek and raised a large family with sons named Reuben, Thomas P., William J., Samuel, John, Harvey G., Henry, David, and daughters Sally, Cynthia, Dorcas, and Mary.
Modern May family research at the Samuel May House has filled in Burris’s outline. Thomas May, Reuben’s father, emerged as one of Pike County’s largest landowners by the 1830s, with more than 1,300 acres on Shelby and Robinson creeks. County tax lists and deed books show him buying up tracts from Crabtree Price and others, while family histories remember him as the practical manager of a sprawling farm whose value ranked near the top of the county on the 1850 and 1860 censuses.
Reuben was Thomas and Dorcas’s eldest surviving son. Genealogist Fred T. May’s “Eighth May Generation” sketch lists him as “Col. Reuben May, born 23 June 1815, Shelby Creek, Pike Co., Ky., married Emmariah (Emma) Virginia Honaker, 5 March 1835, Pike Co., Ky., died 26 September 1902, Vernon County, Wisconsin.” Those dry dates conceal how unusual his path would be. Most of his brothers and cousins remained embedded in the Big Sandy elite, marrying into families like the Leslies, Adkinses, Harmans, and Osbornes and building up Confederate careers and county offices. Reuben, by contrast, would become one of the few members of the clan to leave Kentucky entirely and one of the very few to fight for the Union.
The Other Reuben of Maytown
Part of the confusion around Colonel May’s story comes from the fact that there were actually two prominent men named Reuben in this extended family. The older man, born in 1800, was Reuben May of Maytown on Beaver Creek. He was a son of John and Sarah Phillips May and married Sarah “Sally” Allen in 1825. According to Fred T. May’s sketch “The Old May Mill,” the couple first lived on Shelby Creek, then moved to Beaver Creek, where Reuben acquired an old gristmill from his Allen kin and developed what would become Maytown. He purchased one hundred acres there from his brother-in-law Henry Patton in 1832 and ran the mill until his early death in 1840, leaving Sally with eight children and a posthumous daughter, Reuben Ann.
Burris’s Big Sandy sketch and later Floyd County histories remember this older Reuben as one of the first mill owners on Beaver Creek, an important piece of the local economy long before the Civil War. He was also the brother of Samuel May, whose brick house in Prestonsburg later became the Samuel May House museum. Colonel Reuben, the Union officer and Wisconsin politician, was the nephew who carried his uncle’s name into another generation.
Distinguishing between these two men is more than a genealogical parlor game. It explains why Colonel Reuben’s story runs through both Pike and Floyd counties, even though his adult life carried him away from the Big Sandy altogether.
From Robinson Creek to Goose Creek
By the mid-1830s, the younger Reuben had begun making his own way. Pike County marriage records show that on March 5, 1835, he wed Emmariah Virginia “Emma” Honaker, tying the Robinson Creek Mays to an influential Honaker family whose descendants later turned up in both Pike and Clay counties and, eventually, in Vernon County, Wisconsin.
The best narrative of his early career comes from the book-length biography I Will Uphold the Flag: The Life of Colonel Reuben May, 1815–1902, by Dale and Sharon Sternberg with Fred T. May. That volume, published through the Friends of the Samuel May House, divides his life into Pike County, Clay County, Civil War, and Wisconsin sections and reproduces many of the deeds and court records that trace his moves.
A brief biographical note in the Wisconsin Blue Book, later summarized by the modern Wisconsin Historical Society index and by the Wikipedia entry on May, confirms that he served as an officer in the Kentucky militia, rising to lieutenant colonel during the Mexican War era. He also entered local Democratic politics and held the postmaster’s job at Pikeville before moving deeper into the mountains. Around 1849 he relocated to Clay County, Kentucky, where he managed a four-hundred-acre farm and a salt-making operation along Goose Creek near the community his sources call Mount Welcome.
That move put him in the heart of what historians sometimes call the Appalachian diaspora. Burris’s sketch noticed that many families from the Big Sandy sent one branch west into Indiana, Missouri, or Wisconsin while others stayed on the home waters. In the Honaker and May stories, that process began even before the Civil War. Reuben’s Clay County years, with their mix of salt works, post office politics, and farm management, would prepare him for a still larger leap.
A Union Colonel in a Confederate-leaning Clan
When war came in 1861, Kentucky tried to maintain a policy of official neutrality. On the ground, families chose sides. The May clan became a textbook example of divided Appalachian loyalties. Thomas and Dorcas May’s sons and grandsons appear on both sides of the muster rolls; the Thomas May sketch on Mayhouse notes that “most members of the May family chose to support the Confederacy,” and follows David May and several others into Confederate service and political trouble.
Reuben was one of the exceptions. At forty-six years old and already established as a Clay County businessman, he cast his lot with the Union. The Mayhouse essay on Thomas May states that he “enlisted in the Union Army on September 23, 1861,” and that he eventually rose to become colonel of the 7th Kentucky Infantry, fighting at Perryville, Stones River, Vicksburg, and other major engagements before his three-year enlistment ended.
The detailed military timeline is preserved in federal and state records and summarized in the Civil War Governors of Kentucky project. There, a short note on “Reuben May, Clay County, Kentucky, farmer and soldier,” explains that he served as lieutenant colonel of the 8th Kentucky Volunteer Infantry from January 1862 to May 1863, and as colonel of the 7th Kentucky Volunteer Infantry from May 13, 1863, to October 5, 1864, and that he was wounded at the Battle of Stones River.
The 8th Kentucky’s regimental history, written by Captain T. J. Wright and digitized today, fleshes out the story. Wright and later writers describe how May joined forces with Sidney M. Barnes of Estill County to raise the regiment, gathering volunteers on Barnes’s land and even collecting arms from known Confederate sympathizers. Once mustered into Federal service in late 1861, Barnes became colonel and May lieutenant colonel, with May acting as drillmaster and disciplinarian for the new unit.
Stones River: Holding the Line
The regiment’s most harrowing test under May’s direct command came at the Battle of Stones River near Murfreesboro, Tennessee. During the winter campaign of 1862–63, Colonel Barnes went on leave, and May found himself leading the 8th Kentucky through one of the war’s bloodiest battles.
Accounts compiled in the Official Records and summarized in modern regimental and biographical notes place the 8th Kentucky near the center of the Union line on December 31, 1862. As Confederate assaults rolled forward, units on either side of the 8th broke and fell back. May’s men tried to hold, firing in multiple directions as they were nearly surrounded. One later summary notes that almost every officer still present was killed or wounded. May himself was struck by shell fragments, suffered a concussion, and had his horse shot out from under him before the regiment finally pulled back to the rear.
Kentucky newspapers took notice. A wartime report in the Louisville Courier-Journal on “Friday’s Engagement at Murfreesboro,” cited in May’s modern biographies, singled out the 8th Kentucky and its lieutenant colonel for their role in the fight. In a state where his own cousins wore Confederate gray, that coverage marked May as one of the Big Sandy Unionists whose war record was too strong to ignore.
Colonel of the Seventh Kentucky at Vicksburg
After Stones River, the 8th Kentucky went into camp around Murfreesboro. May recuperated from his injuries in Nashville, and during that period he was promoted to full colonel and assigned to a different unit, the 7th Kentucky Infantry.
From that point on, his name appears in orders of battle and organization tables rather than in colorful anecdotes. The Official Records’ listing for the siege of Vicksburg includes the 7th Kentucky under Brigadier General Albert L. Lee’s and Colonel James Keigwin’s brigade, and specifically names John Lucas as lieutenant colonel and Reuben May as colonel of the regiment. National Park Service summaries for the 7th Kentucky at Vicksburg repeat the same trio of field officers.
The Civil War Governors note and the Mayhouse sketch agree that May led the 7th Kentucky through many of the campaign’s key actions, including Champion Hill, Big Black River Bridge, and the long siege lines around Vicksburg itself. When his three-year enlistment expired in the autumn of 1864, he left the service with the rank of colonel and a reputation as a capable, if sometimes blunt, commander.
Meanwhile, the men he had helped train in the 8th Kentucky went on to write a very different kind of fame. In November 1863 the 8th scaled the cliffs of Lookout Mountain near Chattanooga and planted their flag above the clouds, an episode that became one of the most famous images of the war. Kentucky National Guard historian John Trowbridge notes that later accounts of that exploit drew heavily on Wright’s regimental history and on postwar Kentucky Adjutant General reports, the same sources that feature May in their earlier chapters.
A Southern Gentleman in Wisconsin
While May fought in Tennessee and Mississippi, guerrilla warfare and Confederate raiding made life dangerous for Union families back in Kentucky. According to his later biographers and the Wisconsin Blue Book, his wife Emma and their children fled Kentucky in 1863 and purchased a large farm in Vernon County, Wisconsin, near the town of Viroqua. Reuben joined them there after his discharge in 1864.
A 1931 feature article in the La Crosse Tribune and Leader Press, preserved today in a National Park Service transcription, painted a vivid portrait of the retired colonel on that farm. Writer Robert C. Dunn called him a “typical southern gentleman” and remembered locals’ stories of seeing him ride about his seven-hundred-acre estate west of Viroqua in a large black felt hat and a long coat, an imposing figure whose manners and oratory still carried the flavor of the Virginia and Kentucky frontier even in northern Wisconsin.
The farm itself became one of the showplaces of Vernon County. The county history, published in 1884 and indexed by the Wisconsin Historical Society, includes a biographical sketch of May as a prosperous Jefferson Township farmer and a veteran of both the Mexican and Civil Wars, noting his Kentucky birth and his move north with his family. On the hillside cemetery at Springville, not far away, a gravestone still marks his burial alongside Emma and other members of the family.
Greenbacker, Union Labor Man, and Populist
In Wisconsin, May’s story shifted from battlefield to ballot box. The state’s legislative manuals, the so-called Blue Books, list him as a member of the Wisconsin State Assembly from the First Vernon District for the 1870 and 1872 sessions. He went to Madison as a Republican, having voted for John Bell in 1860 and Abraham Lincoln in 1864, but he never seemed entirely at home in the party.
A close 1875 race for the Wisconsin Senate showed both his ambition and his limits. Running as an independent against Republican J. Henry Tate, he carried Vernon County but lost the district by six votes, a result that prompted a contested-election fight in the legislature but left him out of office.
By the late 1870s he had thrown himself into agrarian protest politics. The Greenback movement, which demanded expanded paper currency and relief for indebted farmers and workers, found one of its most energetic spokesmen in Colonel May. In 1879 he ran for governor of Wisconsin on the Greenback ticket, campaigning across the state but ultimately receiving less than seven percent of the vote.
A decade later he tried again, this time as the Union Labor Party’s candidate for governor in 1890. That campaign revolved around the Bennett Education Law, a controversial measure requiring English language instruction in schools. May and the Union Labor men generally favored the law’s push for public education but opposed the Republican establishment on other labor and monetary issues. He finished a distant fourth, with under two percent of the statewide vote, and the party soon dissolved into the emerging Populist coalition.
Obituaries in the Vernon County Censor and other Wisconsin papers recorded his death at his estate on September 26, 1902, after a brief illness. In those notices, the boy from Robinson Creek had become part of the official story of Wisconsin’s pioneer politicians.
Two Reubens and a Divided Memory
For those still working on Eastern Kentucky genealogy, it is vital to keep the two Reubens straight. The older Reuben, born in 1800, the mill owner at Beaver Creek, was the son of John and Sarah Phillips May and the brother of Samuel May of Prestonsburg. He acquired the old Maytown mill, possibly built before Kentucky became a state, and died in 1840, leaving his widow Sarah Allen with a house full of children and a landmark that survived into the twentieth century.
The younger Reuben, born in 1815, was Thomas and Dorcas Patton May’s eldest son from the Robinson Creek branch of the family. Mayhouse’s Thomas essay traces how he left Pike County before the Civil War, married Emma Honaker, built a salt-and-farm enterprise in Clay County, took the Union side at an age when many men were thinking of retirement, and ended his life on a prosperous Wisconsin farm.
Burris, writing in 1902 from far away in Missouri, probably had the younger man in mind when he wrote that “Reuben May, when the war of secession and coercion broke out between the states, was a colonel of a regiment under General T. T. Garrard in the Federal army” and that he later resigned and moved to Wisconsin. His sketch shows how easily local memory blurred the two generations together, turning the Big Sandy miller and the Clay County salt maker into a single figure who stood with General Garrard’s Unionists and then joined the westward migration.
From Big Sandy to the Driftless
Seen from Pike County, Colonel Reuben May’s life reads as one more chapter in the story of how the Big Sandy seeded the Midwest. Burris’s “Appalachian diaspora” is full of families whose sons and daughters went on to settle towns in Indiana, Missouri, Minnesota, and beyond while cousins stayed on the home creeks. Reuben’s path from Robinson Creek to Goose Creek to Vernon County follows that pattern, but with an added twist.
He carried with him both the privileges and tensions of a Big Sandy elite family. His father had been among Pike County’s largest landowners; his brothers and cousins served in the Confederate ranks and in Kentucky politics; one of his uncles gave his name to Maytown’s mill; another built the brick house that became a museum. Reuben chose differently. He backed the Union when it cost him his Kentucky home, helped train a regiment that fought at Perryville and Stones River, and then reinvented himself as a Greenback and Union Labor candidate in a northern state.
In that sense, Colonel May belongs to both Appalachian and Midwestern history. His story links Pike County deed books and Revolutionary War pension scraps in the May family files to Wisconsin Blue Books and Vernon County farm histories. It reminds us that the Civil War in the mountains was not only a tale of guerrillas and burned homesteads, but also of individuals who carried Appalachian loyalties and conflicts into new landscapes.
Sources & Further Reading
Primary military records for May’s Civil War service appear in the Official Records of the War of the Rebellion and related order-of-battle tables for the Army of the Tennessee, which list him as lieutenant colonel of the 8th Kentucky and colonel of the 7th Kentucky during the Vicksburg campaign. The Portal to Texas History+1
T. J. Wright, History of the Eighth Regiment Kentucky Vol. Infantry (St. Joseph Steam Printing Co., 1880), provides a regimental narrative for the 8th Kentucky, including its formation with Sidney M. Barnes and Reuben May and its early campaigns in Kentucky and Tennessee. Internet Archive
“Reuben May, Clay County farmer and soldier,” in the Civil War Governors of Kentucky digital archive, summarizes his enlistment and promotion dates in the 8th and 7th Kentucky and notes his wounding at Stones River. Civil War Governors+1
Robert C. Dunn’s 1931 article “Typical Southern Homestead Of Col. Reuben May Recalls Many Incidents of His Life,” originally in the La Crosse Tribune and Leader Press and now transcribed by Stones River National Battlefield, offers a near-contemporary portrait of May’s Vernon County years and his reputation as a “typical southern gentleman” on a seven-hundred-acre farm near Viroqua. National Park Service+1
M. T. Burris’s “A Sketch of the Big Sandy, Ky.,” preserved and annotated by the Pike County Historical Society, remains one of the richest early twentieth-century accounts of Big Sandy settlement and includes crucial passages on the Mays of Pike County, their move from eastern Virginia, and his recollection of Colonel May’s Union service and subsequent move to Wisconsin. Pike County Historical Society+1
Fred T. May’s “Eighth May Generation” essays at Mayhouse.org, especially the sketches on Thomas May and on Reuben May of Maytown, pull together Pike and Floyd County court records, land deeds, and family papers to clarify the relationships among John and Sarah Phillips May’s children and to identify Colonel Reuben (1815–1902) as Thomas’s eldest son. MayHouse+2MayHouse+2
The county history History of Vernon County, Wisconsin (Union Publishing, 1884) and the Wisconsin Historical Society’s name index entry for Reuben May provide a contemporary sketch of him as a Jefferson Township farmer and legislator, while the Wisconsin Blue Books and their modern compilation “Those Who Served: Wisconsin Legislators 1848–2007” confirm his Assembly terms and party affiliations. Google Books+2Wisconsin Historical Society+2
For a full narrative, including facsimiles of Kentucky and Wisconsin records, see Dale Sternberg, Sharon Sternberg, and Fred T. May, I Will Uphold the Flag: The Life of Colonel Reuben May, 1815–1902, published through the Friends of the Samuel May House. MayHouse+2AbeBooks+2
Finally, the modern encyclopedia entry “Reuben May” draws many of these strands together into a concise biography, with references to the Courier-Journal, Wisconsin newspapers, and legislative manuals that are invaluable for further research. Wikipedia