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.
“Walrus Rock” at Windy Gap
This hike isn’t worth doing on its own unless you’re looking for a spot to camp and maybe a little geology after packing up - and that’s exactly what I did here. That said, read the note below for a more satisfying hike to Twin Cliffs.
Fall Sunset at Herndon J. Evans Lodge
Gorgeous Fall sunsets from the comfort of a restaurant in the middle of the forest are few and far between. The lodge at Pine Mountain State Resort Park is one of these rare gems. Take in dinner and a sunset along with plenty of color above and below. Book the right room at the lodge, and you can have this sunset on your balcony. Not ready for dinner, walk out to the patio for a slightly less awesome view.
Pineville Overlook - Late Day Fall Views
This short walk leads to a nice view directly above the town of Pineville and provided a great scene before we headed to the lodge for a sunset dinner. When visiting the park, this is a great stop - especially when visiting Chained Rock from the same parking lot.
Roadside Overlooks at Pine Mountain State Resort Park
These overlooks provide nice views and were particularly beautiful with Fall colors on display. As you drive to the top of Pine Mountain, these pit stops serve as an appetizer for even bigger views at Pineville Overlook and Chained Rock.
“Midway” Overlook
Though the view here is more limited than up top at Pinnacle Overlook, you’ll have it all to yourself because there’s only enough room for one vehicle:-) This has a narrow view out to Middlesboro and is a worthwhile stop when touring the overlooks in the region.
Fall at Pinnacle Overlook
This is the main overlook at Cumberland Gap National Historical Park and an easy walk with handicap access as well. The 180-degree view here is outstanding with views of Kentucky, Virginia, and Tennessee looking out to Cumberland Gap.
Lovers Leap Out and Back
This is the first of several overlooks at Breaks Interstate Park that straddles the Virginia-Kentucky border and was mighty gorgeous on my visit with full sun and bluebird skies. Take in the views from the road or walk a couple tenths of a mile for a little closer look.
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!
Combs Overlook on US-23 North
This roadside overlook provides gorgeous views of Pine Mountain above and the town of Jenkins below. It’s a nice, quick stop when traveling US-23 and has a small picnic shelter to enjoy a meal without having to walk more than a couple dozen paces.
Lone Tree to Pitch Ridge Overlooks Loop on Little Shepherd Trail
This was a glorious hike to enjoy the fog covered views west and north of Pine Mountain. The knobs of Kentucky leading into the Ridges and Valleys of the Appalachian Mountains look like islands in the sky and this hike has plenty of spots to soak it all in.
With this being newly created trail, it needs more traffic to better define the path and even out the footing that remains somewhat slanted. I came across a number of downed trees and trimmed back a couple spots to provide a clear path. Please do NOT create side trails around deadfall. The chainsaw crew will be out there when time and resources allow.
The Gazebo at Kingdom Come
The gazebo at Kingdom Come State Park is a must-visit at the park. The view of the valley below is refreshing and southeast facing - making for a great sunrise spot from September through March. Read the hiker notes below for more info.
Log Rock Out and Back
This beautiful, slender, and long arch sits on a ridge running down Pine Mountain’s southeast slope. With a gorgeous view and excellent sit spot just beyond the arch, it is a great place to soak in the mountain views.
Sunrise at Creech Overlook
This drive-up overlook is just off the lane and a half Little Shepherd Trail road just north of the heart of Kingdom Come State Park. It’s rarely busy and over the summertime, provides an excellent sunrise view above the fog below.
Sunrise at 12 O'Clock Overlook
Of the developed overlooks at Kingdom Come State Park, this one is my favorite to visit. Sunrise here was special with fog streaming over the mountain and catching those first rays of light on the northwest face of the mountain.
Bullock Overlook Just Before Sunrise
This is likely the most popular overlook at Kingdom Come State Park thanks to a short, flat walk of only a dozen or so paces to a 180° view. I didn't like the angle for sunrise, so I headed out to a couple better spots at Creech and Lone Tree Overlooks up the road. Nearer the Summer Solstice, this would be the best easy sunrise spot in the park.
Sunset at Lone Tree Overlook
This was a phenomenal sunset at an easy walk up overlook just outside the Kingdom Come State Park boundary. Checkout the sun setting above, behind, then below the clouds - and yes, it was that colorful!
12-Mile Overlook Out and Back
This short walk yields a pair of overlooks that are rarely, if ever, crowded. The views are outstanding looking southwest to northeast over the knobs of Eastern Kentucky with 12 Mile Overlook providing the best of the two views.
Russell Fork Overlook
This roadside overlook is on the west side of Breaks Interstate Park and offers a wonderful view of the Russell Fork below with Pine Mountain setting the backdrop. We stopped here after camping at the northern terminus of Pine Mountain State Scenic Trail across the river in Elkhorn City.
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.