Trail Overview

Little Shepherd is an unpaved route from Harlan KY to Cumberland KY. This route rides across a mountain ridge giving you wonderful views of the surrounding areas. There are multiple pull-offs that function as overlooks to take in the scenery. This trail is stock 4x4 capable, but keep an eye out for blown-out holes. A couple of them are pretty deep. The worst ones all have go-arounds, but they can sneak up on you if you're not on the lookout. The ruts towards the end may require some line choice if your rig lacks some decent ground clearance. There is a great overlook in Kingdom Come State Park at the Cumberland end of the route.

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Difficulty

Deep holes can catch you off guard. Some ruts could catch a running board on a stock rig with poor line choice.

Technical Rating

Hunter Johnson

Apr 11, 2026

Open

Little Sheppard is a wonderful trail, I would highly recommend this trail to any one who’s looking for an easy going trail with beautiful Mountain View’s

Brian S

Mar 13, 2026

Open

I ran this on my 1250GS. It is rough deteriorated trail but very fun running along the top of a ridge. Lots of deep rain ruts, rocky climbs and descents and mud holes

Brent Robinson

Mar 02, 2026

Open

You could tell the trail was deteriorated from the winter snows that had hit the area. The day my buddy and I ran it, it was also raining. While the trail was still passable, the slippery mud made some of the washouts a little tricky to navigate. Also, my buddy was pulling his off-road camping trailer, so navigating that added to the difficulty level. No rain, the trail is still a solid 3, however, if it has been raining in the area I would say it would go up to a 4 or 5. Still doable, but requires a bit more driver awareness. If this is your first time off-roading, go with someone else.

Satch & Sandy Garrabrant

Oct 09, 2025

Open

Very fun trail with great views.

Chris Staton

Jul 20, 2025

Open

Downed tree has been cleared. Fire tower and pond off-shoots worth checking out. A couple of “technical” spots but nothing a stock Tacoma couldn’t handle.

Chris Staton

Jun 25, 2025

Open

Downed tree about 4 miles from the north end, completely blocking trail.

stryker carmichael

May 24, 2025

Open

Jeremy Nelson

Apr 26, 2025

Open

Recent rain so the the trail wasn't dusty. Lots of small muddy spots. Only needed 4x4 for the 2 bigger holes that were maybe 12" deep. Great views through the breaks in the trees. Lots of exposed rock, definitely a rough ride.

Baird Fraser

Oct 29, 2024

Open

We started in Bledsoe. The trail is beautiful. We were a day late on the colors. Tons of leaves on trail. The leaves were cover the so much that you could not see the road. But not a problem. Follow the leaves, lol. Anyway not much to the first part the trail is paved but that ends at about the 20 mile mark and rough road after. It becomes that hard gravel. This outing was not technical but a beautiful ride on a mountain. Plan on turning a lot. There were trees down but they were cleaned up. It can be tight with a wider vehicle. The elevation is among the highest in Kentucky with some great views.

Kyle Hurt

Oct 20, 2024

Open

Robert Johnson

Mar 23, 2024

Open

We saw lots of trees down but cut up and off to the side of the trail. It was a little muddy but the main trail wasn’t difficult at all. We went on a side trail not sure the name of it but it was a little rougher with ruts and decent sized rocks. Very foggy at the start of the trail but it lifted soon after we started. All in all a great day on the trail with the family.

Joe L.

Mar 03, 2024

Open

Rob Ervin

Feb 11, 2024

Open

Went from 421 in Harlan all the way to 160 near Cumberland. Several trees down, but some Good Samaritan(s) have made the trail passable. First tree from Harlan side over 3 foot thick! Saw one other on a SXS and "heard" a group passing on main trail blasting their radio while we were exploring the closed campground. No issues - 4wd only necessary in a few spots due to mud. Probably a "2" when dry.

Jason Simpson

Jan 13, 2024

Open

Tony Cole

Aug 12, 2023

Open