Little Shepherd Trail is a 38-mile journey through some of the most spectacular mountain countryside in the Appalachian Region. Located in scenic Southeastern Kentucky along the Pine Mountain Ridge, the Little Shepherd Trail is a curvy mountain road that twists and turns more than 350 times as it leads you through Kentenia State Forest to some of the most stunning views in Kentucky. The windiest road in Kentucky is not for the faint of heart, but your heart will surely fall in love with this magical drive or ride, with most of this route being paved and some gravel near the end near 119. This trail route connects Coal Train 421 to the Slingshot 119 and has many great spots to visit along the way for all you off-road and adventure touring bike enthusiasts. Don’t forget to visit Kingdom Come State Park for one of the most spectacular views you can experience in Appalachia and The General Store at Pine Mountain Crossing for a cold drink, local country crafts, great food, and of course to see the giant slingshot just a few minutes from this trail route’s end! For more information, click “What’s Around” in our mobile application.