The Wilderness Road, cutting through Cumberland Gap, was a natural invasion route for both the Confederacy and the Union. For the Confederacy, the road led to the rich Kentucky bluegrass country to the north. For the Union, the road led to the Northern sympathizers of East Tennessee and an opportunity to cut rebel supply lines. In late 1861, the Confederacy seized The Gap, from local Home Guard and made it the eastern anchor of a defense line whcih extend to the Mississippi River.
Confederate Brigadier General William Churchwell was placed in command and fortified the garrison during the fall of 1861 and, under his command, contructed seven forts on the north facing slope and cleared the mountains of all tress within one mile of each fort. Needed elsewhere, the Confederates abandoned The Gap in June 1862.
Union Brigadier General George W. Morgan soon arrived to take possession of The Gap. The 20,000 men under his command began building nine south-facing batteries to repel an invasion - but no invasion came. The Confederates under Lt. General Kirby Smith bypassed The Gap with 12,000 men and moved into Kentucky, severing General Morgan's supply line. Without food and still fearing an attack, General Morgan boldly led his men north through enemy territory to safety.
The Confederates returned to Cumberland Gap and strengthened the forts. Many skirmishes took place, as Unionists from Tennessee raided the garrison. In September 1863, a Union force under Major General Ambrose Burnside moved toward The Gap and on September 7, 1863 the Yankees destroyed provisions stored at the Iron Furnace located just two blocks from The Olde Mill Inn Bed & Breakfast. General Burnside also deceived Confederate Brigadier General John W. Frazer into believing that his force was stronger than it actually was. Believing his Confederates to be outmanned, and short of provisions necessary for a long siege, Brigadier General Frazer surrendered the garrison on September 9, 1863.
Lining up along Harlan Road, the Confederates were amazed to see the small force to which they had surrendered. The Gap remained in Union hands until the end of the war. Except for a garrison inspected by Lt. General Ulysses S. Grant in January 1864, when he labeled Cumberland Gap the "Gibraltar of America", there was little excitement. Meanwhile, the war was fought to its end in the South and East. By the end of the war The Gap had changed hands four times, yet no major confrontation took place here.
The Olde Mill Inn's log cabin, built in the 1700's, is the oldest standing building in Cumberland Gap, Tennessee. A "single pen" is a basic log house. To make a single pen, builders join four walls by cutting or notching the log ends in such a way that they interlock when laid horizontally. There are variations on these notches, but the most common are the v-notch, the full-dovetail, and the half-dovetail.
Henry Glassie identified two basic shapes of single pen structures, the square and the rectangle. The square single pen derives from British tradition and has a gable roof parallel to the front with an end chimney at one of the gable ends and single door on the front. A rectangle pen is Scott-Irish in origin and also has a gable roof parallel to the front with an end chimney in one of the gables. The rectangle pen, however, has both a front and back door and, usually, a window to one side of the front door. John Morgan found the rectangle to be the most common shape in his study of log houses in East Tennessee. These pens had dimensions ranging between eighteen by thirteen feet and thirty six by eighteen feet. Most commonly, they had one and a half stories, few were one story and less with two stories. Limestone is easily available in much of the Upland South, and builders in Morgan's study usually chose this stone for their chimneys, over brick or sticks and mud.
Built in the late 1800's, The Olde Mill Inn was thought to be a boarding house for the Pinnacle Wagon Works located across the street (c. 1905). It was built by J.B. Cockrill and his wife Ruth and it was sold to Mrs. Elisabeth Thacker and Children in 1905. It is believed she was a widow as her husband's name would have been listed first on the deed if he were alive. The owner of the Pinnacle Wagon Works, Russell, married one of Mrs. Thacker's daughters, Addie Lenor Thacker, on October 6, 1907, and lived with her and their family at The Olde Mill Inn.
The entire house is built of tongue-and-groove wood, and set on a fieldstone foundation. The Olde Mill Inn Bed & Breakfast is a sturdy home, and is still heated by a wood and coal furnace. Cumberland Gap's railway station was located down the block, and it is likely The Olde Mill Inn was used to put up travelers.