U.S. and Confederate Congressman Alexander Robinson Boteler (May 16, 1815 - May 8, 1892) was born in Shepherdstown. He was a farmer and a businessman, owning a hydraulic cement plant on the Potomac River near Pack Horse Ford (also known as Boteler’s Ford) at Shepherdstown. Boteler was elected to the U.S. House of Representatives as a Whig in 1859, narrowly defeating incumbent Charles James Faulkner, who had previously defeated him twice for the same seat. An owner of 15 slaves (in 1860), he hoped to preserve both slavery and Virginia's place in the Union. At the end of his only term in Congress, he resigned from office and threw his support to the Confederacy. He was the last representative from Virginia’s 8th congressional district until 1870.

From November 1861 to February 1864, he represented Virginia’s 10th district in the Provisional, First, and Second Confederate Congresses. He served on a three-man committee to design and approve the official seal of the Confederate States of America and reportedly contributed to its design. In 1864, he was defeated for re-election by future Virginia Governor Frederick W. M. Holliday.

During adjournments of the Confederate Congress, Boteler periodically served as a colonel on the staff of General Stonewall Jackson. He was a key political liaison between Jackson and Confederate leadership in Richmond, with which the general was frequently at odds. In early 1862, Boteler interceded with Confederate President Jefferson Davis and Virginia Governor John Letcher when Jackson threatened to resign over a dispute with General Joseph Johnston, then-commander of the Army of Northern Virginia. Jackson biographer James I. Robertson, Jr., gives Boteler the bulk of the credit for convincing Jackson not to resign. In June 1862, Boteler carried important military dispatches between Jackson and Robert E. Lee shortly after Lee took command of the Army of Northern Virginia. In January 1863, less than four months before Jackson’s death, he wrote a letter thanking Boteler “for the great assistance which you rendered me by having supplies for the troops promptly forwarded, and for the various other ways in which you contributed to their comfort and efficiency, and to the defence [sic] of that important section of the state [lower Shenandoah Valley]. Not only myself, but also other people there, and the country owe you a lasting debt of gratitude.”

Boteler also counted among his friends Generals Turner Ashby and J. E. B. Stuart, for whom he served as a voluntary aide-de-camp from August 1863 until Stuart’s death in May 1864. In addition to the mounting losses of Southern leaders Boteler knew, the war also exacted a toll on his property. On July 19, 1864, Union troops, under orders from Union General David Hunter, burned Boteler’s Shepherdstown’s home, Fountain Rock, to the ground in retaliation for Confederate destruction of the Maryland governor’s house. They specifically targeted Fountain Rock—and Bedford, the home of Robert E. Lee’s cousin Edmund J. Lee—due to Boteler’s leading role in the Confederate government and military. At the time, Boteler and his wife were away, and his daughters and grandchildren were allowed to evacuate first; the enslaved people at Fountain Rock had escaped earlier in the war when Union troops first seized control of the area. The fire destroyed much of Boteler’s library, early historic images, and several paintings by portrait artist Charles Willson Peale, Boteler's great-grandfather. The site of his former home and plantation is now Morgan’s Grove Park.

After the war, Boteler returned to Shepherdstown and ran unsuccessfully for Congress in 1872 and 1874 as an independent. He was a federal appointee under Presidents Arthur and Cleveland. He was a founder of Shepherd College (now Shepherd University) and helped bring the Shenandoah Valley Railroad (a predecessor to the Norfolk & Western, now Norfolk Southern) through Shepherdstown.

Boteler was an artist and caricaturist of considerable ability and a witness to momentous times. He watched much of John Brown’s Raid unfold at Harpers Ferry and was the first to interview the abolitionist after his capture, and again on several occasions before Brown’s execution six weeks later. In 1883 Century magazine published his account of the raid in the article “Reflections of the John Brown Raid by a Virginian Who Witnessed the Fight.”

Boteler was an accomplished orator and maintained an interest in James Rumsey, the inventor of the steamboat. He produced a manuscript on Rumsey that he tried, unsuccessfully, to publish. He also was an early leader in scientific agricultural practices.