So, in the summer of 1955 the Daniel Boone Trail Committee was formed. They determined the trail route (from Bryan Station Springs in Lexington to Fort Boonesboro), they developed the trail brochure, and they designed the trail patches and medal. The opening day was originally planned for Sunday, April 1, 1956 but was later changed to Sunday, April 15, 1956 to ensure the readiness of the trail. Check-in / check-out stations were positioned at Bryan Station Springs and Boonesboro respectively, with a midway checkpoint at Stiver’s Grocery at the intersection of Cleveland Road and Winchester Road (U.S. 60) in Lexington. Each participant was given a brochure which had trail information on one side, and a trail map on the reverse. The map portion had to be stamped by Kawida Lodge members serving as trail staff at all three locations (Bryan Station Springs, Stiver’s Grocery, and Boonesboro). The ‘stamped’ brochure was evidence of completion of the twenty-mile trail, and the participant was then authorized to purchase a trail patch and medal (patch - $0.75, medal - $2.50). The patch was the Blue Book’s (A .5), which had the opening day date of April 1956 embroidered on it, and the medal was the bronze-colored arrowhead with a green and orange striped ribbon. The (A.5) was only issued to hikers on opening day, and they were instructed to sew it on a plain, white neckerchief. That’s why all of the neckerchiefs look somewhat different, in the fact that every mother / grandmother used different types of white cloth and placed the patch in slightly different locations on the point of the neckerchief. Most everyone followed the instructions, as it’s nearly impossible to find a mint one that was never attached to a neckerchief. Hikers were also given a pocket card (about the size of a business card) to carry as additional proof of trail completion.
After opening day, subsequent hikers could purchase the same medal, but different patches. The Blue Book’s (A1) was issued to Kawida Lodge members who hiked the trail, and Blue Book’s (A3) was issued to non-OA members who hiked the trail. However, hikers were generally allowed to buy one of each. The A1 originally had a pointed bottom, but a subsequent re-order produced a rounded bottom version (A1.5). The A3 had at least three different varieties due to re-orders (A3a), (A3b), and (A3c). Also, repeater pins were offered for a few years to anyone who hiked the trail multiple times. These small pins were designed to be attached to the ribbon of the medal to indicate the hiking of the trail multiple times. Examples of repeater pins included a KY long rifle, a tomahawk, an arrowhead, etc.). A subsequent re-order of the medals also produced a variety having a different bronze-colored arrowhead, but the same green and orange ribbon. The original patches were made by the Geer Company of St. Louis, and the medals were made by the Medal Arts Company of Rochester, NY.
The trail was one of the seven (7) trails which made up the Trail Hiker Award. The others were the Zollicoffer, Mischa Mokwa, Wah-la-hah, Pioneer Mountain, Wilderness Road, and the Bluegrass). The trail remained in its original location until the late 1960’s when it was decided due to increased traffic and safety risks to move it to another course in the Red River Gorge (the part of the Sheltowee Trail which runs through the Gorge). The last Trail Hiker Award was given out in 1972. The trail was abandoned around 1974.