6 Toughest Adventures in Kentucky

There are countless reasons why people explore the outdoors. For some, it’s the desire to commune with nature in the most Zen way possible with less hustle and bustle. For others who live in climates with less-than-hospitable conditions most of the year, it’s to take advantage of beautiful weather while it’s available.

But for a certain group of people, challenging the toughest terrain pushes them outdoors. It’s more than simply getting off the treadmill or spin bike.These folks are all about testing the boundaries of their physicality.

For those looking for a challenge in Kentucky, here are some of the best adventures.

1. Hiking the Sheltowee Trail

The hiking-only Sheltowee Trail spans 290 miles.
The hiking-only Sheltowee Trail spans 290 miles.


If you’re looking for an outdoor challenge ala Cheryl Strayed in her best-selling memoir Wild: From Lost to Found on the Pacific Crest Trail, the Sheltowee Trail in Daniel Boone National Forest is it.

Beginning in the northern part of the state and meandering south for almost 290 miles, the trail ends in neighboring Tennessee at Pickett State Park. Hiking is the only activity that’s allowed on the entirety of the trail, but mountain bikes and off-highway vehicles less that 50 inches wide are allowed on designated portions.

Bears are frequently present, so make sure you store your food and other belongings accordingly. Be prepared to treat your water before you drink it since not all stream water along the trail is safe to drink. Lastly, cell service is spotty at best, so don’t expect to rely on Google Maps to get you from end to end. Make sure someone knows about your travel plans and check in with them and regular intervals.

2. Rapelling the Hidden River Cave

Hidden River Cave in Horse Cave, Kentucky, first opened for tours in 1916. The cave was little more than a garbage dump until 1989, however, when a sewage treatment company took it over and turned it around. Dropping into a cave with such a dirty past might sound like enough of an adventure, but that’s not what puts Hidden River Cave on this list. It’s the option to zipline across the mouth of the cave as well as rappelling down its face that makes this one a jaw clencher. You don't need a lot of skill, just plenty of guts (and this is one adventure that is suitable for kids ready for a thrill).

3. Rafting the Big Sandy River

Near Breaks Interstate Park is where you’ll find the Big Sandy River responsible for carving the 1,600-foot-deep canyon it meanders through. While states other than Kentucky might be better know for whitewater paddling, Russell Fork is piled high with "free-falling, steep-dropping, nail-biting rapids" that creates one of the toughest runs in the eastern U.S., earning itself a Class V rating. Only experienced and advanced rafters are advised to undertake Russell Fork. Available only during four scheduled-release weekends in October every year, the season is short, so make your plans well in advance.

4. Traversing the Sand Gap Trail

The Sand Gap Trail is the most strenuous trail in Natural Bridge State Resort Park within the larger Daniel Boone National Forest. Taking four to six hours to complete, one challenge of this trail is a lack of shortcuts. Another aspect of the trail that makes it tough is the level of solitude you’ll find out there. Expect a lot of slightly eery time alone, far from the sights and sounds of civilization.

5. Undertaking the Wild Cave Tour at Mammoth Cave

When first entering Mammoth Cave, it’s difficult to comprehend how far this subterranean world extends.
When first entering Mammoth Cave, it’s difficult to comprehend how far this subterranean world extends.

Anissa Wood

With some 405 miles of connected cave-scapes, Mammoth Cave is the world’s longest known cave system, and there’s even more that has yet to be mapped. There are a variety of guided tours through the cave, including ones like the Frozen Niagara Tour that are better for small children and folks that don’t love stairs. But the Wild Cave Tour seriously ups the ante. If you opt for the latter, be prepared for claustrophobia-inducing scenarios and hundreds upon hundreds of stairs through five miles of the most difficult sections of the cave.

6. Climbing the Golden Ticket

For those who get their kicks by scaling rocks, Golden Ticket (tentatively rated 5.14d) at the Red River Gorge is as grueling as it gets. Located at the Chocolate Factory Crag, this route was bolted by the renowned climber Kenny Barker after many before him failed. Golden Ticket has earned a reputation as the toughest climb at the Red, which is saying a lot considering how many 5.12 and above routes are established. Only top level climbers have any business on this climb, but if you’re willing to put in the time and training, you may be able to add your name to those who have sent this wild line.

Written by Cinnamon Janzer for RootsRated in partnership with Kentucky Tourism and legally licensed through the Matcha publisher network. Please direct all licensing questions to legal@getmatcha.com.

Featured image provided by Aaron Vowels

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