Explore the best rated trails in Harlan, KY, whether you're looking for an easy walking trail or a bike trail like the Harrogate Walking/Biking Trail and Cumberland Gap Greenway . With more than 12 trails covering 79 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
I rode this trail today starting at Jane Beshear TH in Royalton south to Tip Top Tunnel and then back up to Hagerhill and returned to Jane Beshear. The trail to Tip Top was in pretty good shape but the scenery was saddening at time with peoples living conditions. The last couple tenths of a mile to Tip Top Tunnel was some rough gravel but walkable at a minimum and rideable if you are so inclined. North of Jane Beshears to scenery is wonderful especially north of Gun Creek Tunnel. Just south of Swamp Branch TH I startled a group of horses in their enclosure and a big white pyrenes guard dog got up and stared at me. He figured I wasn't a threat, so he just watched me ride by without incident. I did get have several encounters with dogs south of Jane Beshears TH but only one chased me and I was able to ride away from him. I think he was just chasing me off "his" section of the trail as he stopped chasing me when he reached the end of his property. The north end of the trail stopped at Big Sandy Heating and Cooling a little bit before the endpoint shown on the map.
Very nice trail for my wife on her disability scooter and me on my e bike.
On 9/16/25 I was chased twice by a dog at first or second house west of Swamp Branch TH. Fortunately I was able to pedal faster than dog could run. Dangerous for children.
I rode the trail out and back from Jenny’s Creek trail head to the dead end at Tip Top Tunnel. Pavement is perfect! Mostly tree canopy! Lots of small road crossing but very little traffic. The huge metal single file guard rails were strange and completely annoying. Strange that there so many - at bridges, road crossings, and even in flat straight sections. Annoying because they were only slightly wider than a road bike bars and you had to slow down and ease through. The facilities were completely toxic - awful. Not cleaned in years. Only 1 water fountain. Please do better.
Dropped in at Gibson station and tried to ride towards Cumberland gap. It was a no go very quickly because the trail is no longer maintained by the national park.........Budget cuts! We were riding on overgrown grasses/weeds which is no fun at all! Turned around and rode towards Wilderness Road State Park. Lovely ride in the shade with just a few spots that were wet from the heavy rains from the last few days. August 14 was hot and humid with some mosquitoes along the trail! Did a few loops in Wilderness Rd., State Park where they were having some actual reenactments back in the fort! All in all lovely country views. The buffalo were in the corner right next to the trail...sat at the picnic table and watched them chew! There was a new calf! eat all get
Great trail... I started at Jenny's Creek trailhead, I didn't see another biker on the whole way up to Tippy Top Tunnel.. (it said no trespassing, but I just had to check it out).. it was 25 miles to the tunnel.. I just wished that it went all the way through the tunnel, but was told later by someone that the tunnel had a cave in, so I don't suppose it will ever be a complete connection (sad) that would have been fun to ride through there.. but I started on my way back down and finally ran into another biker, he's the one who told me the history of the tunnel and how he use to ride horses through there.. ran into a group of riders, about 30 of them on the way back down.. I say down because i coasted a lot of the distance in a lot of places.. so it's a steady climb to tippy top, but nothing major..
My only bad experience of the trial.. there's a home a few miles into the ride that has dogs.. and those dogs was on my heals.. they wasn't there on my way back... that was my only bad experience.. maybe I should carry some kind of pepper spray or something to get ride of threats like that..??.. I rode all the way back down to the very end of the trail.. and started heading back to my car.. my other bad experience (my fault) I ride an e-bike and my battery ran out of juice.. that was ok... I was almost to the car anyway.. but it was an awesome ride.. took me 3 hrs to get there.. I live in Ohio.. I spent the night in Paintsville, I visited Jenny Willey Start Park which is that area.. nice park..
May head back down there next year..
I live in Kentucky and was excited to try this trail. I’ve ridden 33,000 miles on 278 trails and I can easily say I’ll never go back I had two large Dobermans chase me, nipping at my heels and jumping up on to my legs. They caused me to lose my balance and crash on my ebike. I wound up needing two shoulder replacements. I’ll never go back
Per mile this is the most beautiful trail we have ever been on, and we have been on quite a few. The scenery is just gorgeous. You will want to go slow and watch the overhead cliffs on one side and listen to the rushing river on the other. Going slow is fine because the surface is not that great. You will be on the brakes on the way down and in low gear on the way back. Go in the early spring so you can see all the scenery and the river is rushing.
A few soft sandy spots where the trail has had fresh crushed gravel brought in, but a nice easy ride. 2 first time riders, 2 mediocre riders, 2 kid trailers. Visitor center is very nice
We’ve ridden many rail trails across the country and this one is really great. All paved, mostly flat with some gentle grades. Dogs that some reviews mention are all in fenced kennels, none loose on the trail. We stopped at Griffith Farms for soda and some great farm treats - really fun. Mix of woods, creeks, bridges, family farms, lots of wildlife.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Scan the QR code to get TrailLink on your phone
