
Austin Gap with Ravens Nest, Staircase Caves, and Skyview Rock Shelter
This is a spectacular hike and leads to arguably the most interesting geological formations on Pine Mountain’s 120+ mile ridgeline. At the top, you’ll enjoy massive views east and south across Virginia, a pair of small caves, and an arch complex with a skylight that is absolutely stunning. BUT, you’re gonna have to work for it - see the notes below.

Count's Cabin to Big Toe Rock
Of all the day hikes on Pine Mountain, this is a fast favorite! Starting at the base of the mountain on the Virginia side of the border, this ascends to the ridge providing truly spectacular views of Kentucky. Along the way, enjoy a relatively rare sight at Pine Mountain Natural Bridge - a conglomerate sandstone arch. And, take the spur to a deep rock house that is believed to have been the source of seven different sulfur springs on the mountain. This is a great hike!

Little Shepherd Trail from Kingdom Come to US-119 - Pine Mountain State Scenic Trail
What an exciting weekend on Pine Mountain! We backpacked the brand new Little Shepherd Trail Section of Pine Mountain State Scenic Trail (PMSST) between Kingdom Come State Park and US-119 TWICE, and it was AWESOME! There are SIXTEEN named overlooks on this segment with some of the biggest and best views anywhere in Kentucky! If you don’t have this trail on your list, put it at the top right now. It’s that good.