Alfred Royal Wynne (1800-1893), a trader and merchant in Castalian Springs, built this stagecoach inn along the Knoxville road in 1828. Although Wynne was a slaveholder and a Democrat, he was also a staunch Unionist who strongly opposed secession, but after Tennessee left the Union he abandoned his former allegiance and supported the Confederacy. Like many younger Southerners who favored secession, two of Alfred and Almira Wynne’s sons, Andrew and Joseph Wynne, enlisted soon after Abraham Lincoln was elected president in 1860 in the 2nd Tennessee Infantry under the command of their neighbor, Col. William B. Bate, and their younger sons Valerius and William Hall Wynne also enlisted; William died of disease the next year. Early in 1862, Confederate cavalry raids aimed at disrupting Federal supply and communication lines were launched in northern Middle Tennessee, and Col. John Hunt Morgan’s command operated in the area and at times stopped at Wynnewood to eat; on one occasion Morgan signed the guest register for one of Wynne’s daughters. By April, the Union army had established a military post in the southwestern corner of the Wynne farm and surrounded the fortified camp with log and stone earthworks. Although the Federal troops generally behaved themselves, they caused extensive damage to the trees, fences, and fields. After the war, Wynne sought $6,540 in damages, but the U.S. government rejected the claim because he had not remained loyal to the Union.