Beginner Off-Road Trails Near Middlesborough, Kentucky

This trail intersects with 16 Creeks trail and runs out a long stretch of high ridges with some excellent views of the surrounding area. The east side of the trail goes to several cell/radio towers…
Learn more about High Ridge Towers

The Sandlick Trail is an easy trail ride that navigates through thick Tennessee mountain laurel, crosses several small streams along the way, and has a beautiful waterfall called No Business. This trail is one of…
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This is a gravel/dirt road uphill to a large open field with roads. The property includes open range horses and cattle, and there are lots of side trails to adventure onto. The trail can be…
Learn more about Mary's Wild Horse Trail

Main Forest Road runs from the entrance to Chuck Swan State Forest until it meets Forks of River Road, which will take you to the very end of this route. It's relatively smooth in comparison…
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This route traverses from the southern portions of Chuck Swan WMA to one of the more remote areas on the northern border. Along this route you'll find some easy but fun roads, a natural freshwater…
Learn more about Mossy Springs

This route provides a bit more challenge and adrenaline than the majority of the roads in Chuck Swan WMA, but still keeps it well within the capabilities of most stock and slightly modified 4x4s. Along…
Learn more about Lost Creek & Clear Creek

This loop gives you a bit of everything there is to see in Chuck Swan WMA. This route is slightly rougher than Main Forest Rd, but still passable by capable 2WD vehicles except during the…
Learn more about Big Loop & Big Springs

This is a well-maintained gravel road that goes from Highway 25W to the elk viewing tower at Hatfield Knob. There are several viewing areas and lookouts on the way up as well, so keep an…
Learn more about Elk Viewing Tower Road - Trail 25

Crumely Loop is a mellow 2.6-mile forest road tucked into the heart of Chuck Swan State Forest. Like all the roads here, it's an active logging route, so keep an eye out for trucks and…
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This trail is a maintained gravel road that connects several other popular trails. At one end it connects to Trail 19, and at the other end, it connects to Trail 25. Trail 37 is also…
Learn more about McCormick Cemetery Road - Trail 24

Wolf Knob is an 8.2 mile out and back trail that ends at a closed forest service gate with a grassy road extending a ways beyond it. There is one nice campsite close to the…
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This is a well-maintained gravel road accessible by any stock vehicle. It starts just off of I-75 and is a nice gravel road with a few potholes and puddles. Any stock truck or SUV can…
Learn more about Flatwoods Road - Trail 1

Jellico Creek Road, aka Rock Creek Road, connects to Angel Mountain Road and Little Rock Road to the west and then transitions to pavement to the east. Along the 2.75 mile route, you'll find several…
Learn more about Jellico Creek Road

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…
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This is a road along the top of a ridge that has recently been cleared for logging. The road is wide and flat and easily accessible by most stock 4x4s. It gets a little bit…
Learn more about Trail 4 - Short Mountain Road

Trail 29 is a longer trail running from east and west near the far west side of the Black Mountain ORV Adventure Area. The trail ends on the west side at a private property which…
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The majority of this trail is flat (the flattest in the park) with some shallow water/mud holes with solid bottoms. The terrain is small gravel-like rock mixed with softball-sized rocks. This drive is very picturesque,…
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Stephens Knob is relatively unassuming for the majority of its 7.7-mile length. It's a very well-maintained gravel road. During the winter, nice views are available off of the north side. There's a split at the…
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Ryans Mountain Road is a well-maintained gravel route that's two vehicles wide for the majority of its nearly six-mile length. It climbs from Kentucky State Highway 1470 before dropping back down from the ridgeline in…
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Trail 25 is an enjoyable drive. This dirt trail has very few rocks and little elevation. It is fairly wide and away from the very edge of the mountain. There are some large, shallow water…
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Angel Mountain Road is a short out and back that intersects with Jellico Creek Road and Little Rock Road. Along the route, you'll find several small rock overhangs and outcroppings, locally known as "rock houses".…
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Little Rock Road connects Stephens Knob Road with Jellico Creek and Angel Mountain. The northern portion is mostly gravel and better maintained the southern portion where you'll find a few water crossings and rocky sections.…
Learn more about Little Rock Road

Trail 12 splits into two parts in the OHV area. It is divided by private land. For mapping purposes, this trail has been labeled "12a" and "12b". 12b is an easy drive and is a…
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Trail 12 splits into two parts in the OHV area. It is divided by private land. For mapping purposes, this trail has been labeled "12a" and "12b". 12a is an easy drive and is a…
Learn more about 12a

Gabe's Branch Road travels between Kentucky State Highway 221 and Kentucky Route 2008. This trail is a gravel and rock road that is somewhat maintained. There are a few small ruts, but they are easy…
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Trail 20 is a dirt trail and just under 2.5 miles long. It's a very scenic drive that weaves along the mountain's edge. There are some mild elevation changes and it's a great way to…
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One of the best waterfall hikes in Kentucky lies along this well-maintained gravel forest road. Dog Slaughter Tail connects to Cumberland Falls Trail, with a great view coming along the bottom of the falls towards…
Learn more about Dog Slaughter (FSR 195)

This trail is just over 2 miles long and is a great opportunity to see the Black Mountain trails without getting too crazy. There are also a couple of small waterfalls to enjoy. The terrain…
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This route starts just off of I-75 and has you up in the mountains within minutes. While the top portion of the track is relatively smooth and graded, the switchbacks ascending the ridge include washouts,…
Learn more about Massengale Mountain

G58 - Cambria Hollow is a mud-hole-ridden trail with hard bottoms. There is no fear of sinking a vehicle in these puddles, but they can give you a good splash. This trail can lead you…
Learn more about G58 - Cambria Hollow