Kentucky Trails

Lexington, KY: Sheltowee Trace, Daniel Boone National Forest

Follow cliff bands on this 18.3-mile point-to-point to some of the East’s largest natural arches.

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To appreciate this 18.3-mile section of Kentucky that’s been tunneled and pummeled by the Red River, you’ll need to brush up on your Daniel Boone history. In 1778, the legendary pioneer was taken prisoner by the Shawnee tribe, only to be adopted into the chief’s family and given the moniker Sheltowee, which means “Big Turtle”—a reference to his powerful, compact physique.

You’ll follow turtle-shaped white blazes into the trees from the Corner Ridge parking lot, scout dry-foot routes across a handful of creeks, and haul yourself up the Red River Gorge’s arch-topped bluffs. The first 3.5 miles follow Salt Fork to its confluence with Gladie Creek and a shallow, 100-foot ford. Follow a bluff for two miles, culminating in views over pines, maples, and oaks. Look for black bear; Boone used to hunt them around here.

At mile 5.5, cross Klaber Branch creek before passing a junction with the Bison Way Trail. After .5 mile, a side trail leads to Indian Staircase, a test of mettle that pays off with a view of the sprawling valley below. Continue .4 mile to Indian Arch, a 20-foot sandstone span sitting on the ridge between Sargent and Greasy Brooks. Set up camp and climb the arch from the west for an unobstructed view of the gorge.

Next day, cross Greasy Brook and swing north around a pinnacle called Cloud Splitter. In 1.7 miles, reach a 200-foot suspension bridge over the Red River, with Chimney Top Rock to the southeast. Follow the trail in the Chimney Top Creek’s floodplain, then climb to a treeless peak. Gray’s Arch, tall as a full-grown pine, stands to the northwest.

Another 3.5 miles takes you past mini waterfalls along the Whittleton Branch. Cross over the Bert T. Combs Mountain Parkway, and pick up the Whittleton Arch Trail. Hike 1.2 streamside miles to a .2-mile side trail to the arch. Return to the trail and track 1.3 miles to the Natural Bridge parking lot.

SHUTTLE: Sheltowee Trace Outfitters; (800) 541-7238

PERMIT: Three-day DBNF Recreation Fee Hang Tag ($5, at gas stations)

GEAR UP: Phillip Gall’s. 1555 E. New Circle Rd., Lexington, KY; (859) 266-0469

MAP: Free;

-Mapped by Stuart Peck

Trail Facts

  • Distance: 29.5



Location: 37.89504, -83.603511

Follow turtle-shaped white blazes southward into the trees from the Corner Ridge parking lot.


Location: 37.857035, -83.595692

Scout dry-foot routes across the first of a handful of creeks here.


Location: 37.842596, -83.61148

Pass junction with the Bison Way Trail. Prepare for a number of wide switchbacks gaining elevation and riding the ridges of several peaks.


Location: 37.84611, -83.617131

After .5 mile, take the Indian Staircase side trail for a fantastic view of the valley. Continue .4 mile to Indian Arch.


Location: 37.842729, -83.616509

Set up camp and climb Indian Arch from the west for an unobstructed view of the gorge.


Location: 37.827819, -83.624282

Cross 200-foot suspension bridge from the west side to the east side of Red River, with Chimney Top Rock to the southeast.


Location: 37.810508, -83.634474

Here, you’ll have a good opportunity for some photos: a scenic outlook at a treeless peak overlooks Gray’s Arch to the northwest.


Location: 37.78534, -83.661602

After 3.5 miles of mini waterfalls along the Whittleton Branch, cross over Bert T. Combs Mountain Parkway to pick up Whittleton Arch Trail.


Location: 37.77795, -83.676405

At the Natural Bridge Parking Lot, take a shuttle back to your car.