Osborne Bend Trail | 8.5 Mile Loop

Osborne Bend Trail Map

Osborne Bend Trailhead Location | Google Maps

The Osborne Bend Trail is one of those trails in the Red River Gorge that is a hot button topic amongst avid hikers. People either hate it or love it, plain and simple. For the uninformed, this trail is considered quite dull and easy to navigate with no real scenery to make it a worthwhile journey. After its initial ascent, it spends most of its path shrouded in darkness under a thick canopy as you navigate a long ridge that completely encircles Copperas Creek. To the initiated however, the Osborne Bend Trails “eastern half” is one of the more dynamic in the gorge. A little bit of research into this particular area can yield coordinates to some of the Red River Gorges oldest landmarks like Eagle Point Buttress, Eagles Nest and Moonshiners Arch. Many of these UNOFFICIAL points of interest can be found on the kyarches.com database and similar websites. 

Before beginning, a word of CAUTION: Parts of this hike include UNMARKED TRAILS, not registered on any official map of Red River Gorge Geological Area. This hike includes scrambling over exposed cliffs and rock ledges that have resulted in deaths and injuries. Do not venture out alone. Use common sense and do not attempt anything that would put yourself or others at risk or harms way. This is NOT meant to be an instructional article, but a recollection of my own journey. The Red River Gorge is home to several species of venomous snakes as well as black bears. Be Bear Aware. Do your own research before going out and attempting any hike!

Osborne Bend Trail (8.5 Miles)

To get started, we enter the Red River Gorge and head on over to the Osborne Bend Trailhead along KY 715. The trailhead is almost exactly halfway between the Nada and Pine Ridge entrance to the park. On either side of the Osborne Bend Trail are the beginnings of two well known UNOFFICIAL trails in the area, Copperas Creek Trail and the Eagles Nest Trail, as well as access trails to two popular rock climbing walls. This is one of the few parking lots with a vault toilet so it is usually full. In any case, you might have to park further past the trailhead or before it in one of the many roadside pullouts available. Whatever you do, just make sure to park in a designated spot so as to not obstruct traffic or get your car towed. Though the full extent of Osborne Bend is 8.5 miles from end to end, we’ll only be hiking a 1.5 mile out and back section beginning at the parking lot.

Moonshiners Arch & Skylight (-37.821111, -83.571666)

This hike kicks off pretty quickly with one of the largest natural arches per volume in Red River Gorge, Moonshiners Arch. This is one of two arches in Kentucky that go by the same name, with the second Moonshiners Arch located in Whitley County in the southern half of the Daniel Boone National Forest. As one of the more popular off-trail arches here, there is a well traveled and easy to navigate path to it. Within the first 0.16 mile along the Osborne Bend Trail, you’ll come to a “Y” intersection with the main trail continuing uphill to your LEFT and a smaller trail heading downhill to the RIGHT. Take the RIGHT path. This will lead a short distance to a dead end at a popular backcountry campsite perched above a sheer cliff. Once you reach this area, you are standing directly on top of Moonshiners Arch.

Careful to avoid the edge of the cliff, I had to rummage through the area to find the small path that leads to a scramble down a narrow ravine on the backside of the arch. Along the way I had to stop myself short of stepping into a wide gaping hole in the cliff, this is Moonshiners Arch Skylight. It leads directly down a 15 foot drop into the cave below. Sidestepping this, I found the well worn path circling back downhill to the entrance of a large cave, this is the rear entrance to Moonshiners Arch. Looking in through its distinctive “tear drop” shaped opening, you really get a sense of just how enormous this natural structure truly is.

At 11 feet high by 16 feet wide, it doesn’t sound all that impressive until you see it in person. Those measurements only take into account the opening we scrambled through to get in. Its front entrance is nearly 5 times larger. This arch was created by a partial roof collapse through the section we entered. Originally beginning as a small fracture in the cliff wall, the constant lowering and raising of the nearby Red River caused flood water to erode the brittle limestone into a cave and eventually the rear section of ceiling followed suite. Due to the skylight creating a natural chimney in the cave ceiling, many people have taken to camping within the arch which sprang up its other nickname, Hunters Arch. A short scramble through the front of the arch will take you to a path which goes all the way down to the river.

Trap Door Arch (-37.82219,-83.57266)

Heading back to that “Y” intersection we first split off onto, we made a RIGHT turn to head back north onto the Osborne Bend Trail. Finding Trap Door Arch requires checking in on our coordinates for the arch while simultaneously continuing on the trail. Learning how to use a GPS Tracking App comes in handy when you’re out hunting for arches. There is no direct route to Trap Door Arch straight from the Osborne Bend Trail, but about 50 yards before reaching it, you can spot a small side trail heading LEFT (WEST) towards the bottom of a sheer cliff wall. Navigating over some rock fall, we dip in and out of several shorter cliff overhangs before arriving at a massive one measuring close to 100 feet tall. At the very top of its ceiling, one can just barely make out the fact that a giant square shaped portion of rock has fallen from the structure and lodged itself into a tight corner. This is the “trap door” of Trap Door Arch. Without climbing gear, it is impossible to reach so this is as good a view as you’re going to get.

Unicorn Arch (-37.82527,-83.57222)

If there was ever an easier arch to spot just off-trail (literally 10 feet away), then I haven’t found one better than Unicorn Arch. This master of deception lies incognito directly above the Osborne Bend Trail, but you wouldn’t notice it unless you were looking for it. Coming back to the Osborne Bend Trail after checking out Trap Door Arch, it only takes a few minutes of uphill hiking to reach Unicorn Arch. It helps to have seen pictures of it beforehand to know what you’re looking for, but even so GPS coordinates would suffice. The arch itself is made up of a single pillar, jutting out sideways like an arrow from the side of the cliff directly on your LEFT, maybe 12 feet up in the air.  Since it’s located perpendicular to the trail, one can only really see it just before reaching it or looking back after passing it. If you make it to the staircase leading up the ridge then you’ve gone too far.

Noticing on my map that I was lined up right beside it, I looked over and spotted a rough path climbing up to the ledge the arch is located on. It is a steep 10 foot high scramble, but something manageable for most agile people. Even after visiting this arch on a few occasions I still can’t fathom why anyone named this “Unicorn” Arch. I think its nickname, Hemlock Arch, is much more fitting due to the thick forest of hemlock trees surrounding it. There is a wide shelf underneath the 8 foot long span, big enough to crawl through to the other side. This makes a nice vantage point to sit out on and enjoy a pack lunch while watching other hikers oblivious to your presence, walk right past!

Osborne Bend Arch (-37.82583,-83.57138)

One of the sneakier arches to find on the Osborne Bend Trail in my experience has to be Osborne Bend Arch. You could literally stand on top of it and probably see the trail over the thickets of rhododendron, but unless you find a series of ledges leading up to it you won’t even stand a chance. GPS coordinates are not always exact and more often than not are only to be used as a relative location. Which lead me to make three separate trips into the Clifty Wilderness to finally see it for myself. From Unicorn Arch, we hopped back on the Osborne Bend Trail and continued north for another 0.16 mile until reaching the rockshelter directly in front of the switchbacks leading onto Osborne Ridge. As soon as you climb onto the ridge, there is a well marked path on your RIGHT AT AN ANGLE that curves behind a large rock outcropping. This is the path. 

Following this you must crouch under some fallen trees and a low hanging cliff overhang till you reach a couple of ledges leading up into a gap. You’ll be tempted to follow the small side trail through the thicket of rhododendrons, but I found that I couldn’t find the ledges unless I crawled through the tunnel directly against the rock wall. Finding this ledge is crucial to finding the arch as it is located a few feet away from here. On my first attempt I took the off-trail path straight across the correct one which took me to the top of the ridge, bypassing the arch altogether. Thinking the arch might be located lower along the cliff, my second trip lead me to explore the valley below Osborne Bend Trail. On my third attempt I was equally lost until by happenstance, I stumbled onto the ledges and figured “why not climb these and check it out”.

After the scramble, turn LEFT and the arch should come into view within a few moments. Osborne Bend Arch is a surprisingly large span nearly 25 feet long and 5 feet high. This alcove type arch has a large opening on its northern side which you can sit under or crawl through to the other side. During late June through early July, the entire thing is surrounded by the fragrant and colorful blooms of mountain laurel and rhododendrons (which I caught on my first trip). Nonetheless, I was thrilled to finally see this gorgeous natural formation for myself and scratch it off my list. For most people finding these first 4 arches, which are barely off-trail, shouldn’t be too much of a challenge and can even spark a greater curiosity and appreciation for all of the natural wonders hidden within the Red River Gorge. At least that’s the affect it had on this restless hiker.

Brewer Natural Bridge (Clifty Wilderness)

Those looking for a bit more of a challenge can step up their game by searching out Brewer Natural Bridge. As you might have notice, I did not provide the coordinates for this one. That’s because this is still a well kept secret reserved for only those willing to put in the extra work to find it. Though there is no direct route to this arch, it is just an earshot away from the Osborne Bend Trail. Hiking nearly another 1 mile north on the main trail from where we found the Osborne Bend Arch, we had to take a 0.5 mile off-trail excursion east through the forest to the top of a drainage that separates Eagle Point Buttress from the Osborne Bend Trail Area. A map, compass, and gps coordinates are required for this one as its easy to get turned around in the deep forest of the Clifty Wilderness. As an added bonus, along the way you’ll pass the precipice of Memering Falls, a little known and remote 20 foot waterfall. 

There is a lot to explore in this area and even these few hidden gems are only a scratch in the surface of what one can find with a little extra effort. For anyone not familiar with the Osborne Bend Trails next door neighbor, head on over to our Copperas Creek article where we explore some of the hidden arches and waterfalls along this famed UNOFFICIAL trail. Up nex,t we’re driving up to the Chimney Top Rock Area to find another unofficial trail to one of the largest waterfall arches in the gorge, Cherokee Arch. This is one of the toughest off-trail hikes we’ve undertaken yet, descending a remote ridge covered in secret arches that hardly anyone visits. Stay tuned for this upcoming adventure and as always, see y’all on the trails!