Rising to an elevation of 4,930 ft in the Highlands and Cashiers area of Western North Carolina, Whiteside Mountain is a notable peak along the Eastern Continental Divide.  Prominently featured in the Cherokee “Legend of the Spear Finger” and home to “The Shadow of the Bear”, the mountain has long been a popular tourist attraction dating back to the 1800’s. Becoming a part of the Nantahala National Forest in the 1970’s, the mountain is surrounded by a handful of unique ecosystems brimming with rare and endangered plants that put on a spectacular wildflower display each spring. The area boasts a 2.0 mile family friendly trail that ascends the mountains peak and loops around to a dozen stunning overlooks of the surrounding region with views as far south as Georgia and South Carolina.

Whiteside Mountain Trail | 2.0 Mile Loop

Whiteside Mountain Trail Map Brochure

Whiteside Mountain Trailhead Location | Google Maps

Nantahala National Forest Map

Approximate path of Whiteside Mountain trail near Highlands, NC using Gaia App.

If you’re visiting the Highlands and Cashiers Area of Western North Carolina, chances are you’ve seen or at least heard of Whiteside Mountain and “The Shadow of the Bear”. Drawing in thousands of tourists for about a half-hour toward sunset in mid-October, a small shadow is cast toward the valley below the southern slope, slowly growing into what appears to be the shadow of a huge bear on the lower reaches of Whiteside Mountain. This mountains iconic cliffs, which are the tallest in Eastern North America, have an unmistakable sheen that make them appear to be covered in sheets of ice and stand out amidst the vibrant greens of the surrounding valley. While most of my time in the Cashiers area has been spent chasing waterfalls like Whitewater Falls, Silver Run Falls, Glen Falls and exploring the waterfalls of NC-281, I had to specifically plan a stop at Whiteside Mountain to see these  700 ft tall cliffs for myself.

 
Trailhead at Whiteside Mountain Scenic Area.

Driving along U.S. Route 64 from Cashiers to the Whiteside Mountain trailhead, one gets their first glance of this mountains massive cliffs from a popular roadside pull-off named, the Big View Scenic Overlook. The aptly named Whiteside Mountain Rd takes visitors through one of the areas most prestigious private neighborhoods, Wildcat Cliffs, before veering off into the trailhead parking lot 400 ft below the mountain summit. The Whiteside Mountain Recreation Area features a large parking lot with vault toilets and a picnic area. There is a small day use fee of $3 which can easily be paid for electronically. Just remember to leave the tag on your cars dash before you venture off on your hike. If you don’t have a map of the trail, stop by the kiosk and take a photo of the map provided here.

This is where the trail splits with the right fork going straight up the mountain and the left fork taking a gradual climb around the back to Devils Courthouse.

From the trailhead, a short stairway leads up to a steep spur trail that connects visitors to the main 2.0 mile loop. While the Whiteside Mountain Trail is considered strenuous due to its direct route which takes a steep 400 ft climb, this part can be easily skipped by tackling the trail clockwise. If you take the LEFT path at the fork, the trail has a more gentle and gradual climb around the back of the mountain that just about anyone can manage. This part of the trail is actually an old roadbed which was part of a tourist attraction that existed here back in the 1970’s before the Forest Service bought the mountain. Fascinatingly enough, the theme park also included a post office near the mountains summit where tourists could mail post cards. Wanting to get the hard part over first and then coast through the rest of the hike I decided to take the RIGHT at the fork and go straight up the mountain.

Small ladder along the 400 ft climb to the summit of Whiteside Mountain. 

Winding its way up nearly 400 ft in a series of switchbacks, the straight shot up only accounts for a tiny 0.21 miles of the 2.0 mile loop. The key to tackling it is to find a nice, smooth pace. Views from down here are almost non-existent, but I found the side of the trail to be filled with a ton of colorful woodland ephemerals which helped take my mind off the slow march up. Gorgeous, white blooming serviceberry and chokeberry trees grow in abundance up here along with mountain laurels which are soaking the air in their sweet scent. Near ground level, false Solomons seal, white snakeroot, catesbys trillium, trout lilies, wood lily, and wood betony create a tapestry of color throughout the wooded slopes. Because of its popularity with tourists, this trail is regularly maintained by the Forest Service, making it a breeze to hike along. Right around the third switchback, you’ll find a three-rung ladder spread out over a part of the trail that is badly eroded. Two more switchbacks over from this and the trail passes over a long boardwalk to a series of staircases that take you just shy of the summit. After a short walk up through a wooded clearing, you’ll catch the first of many overlooks found on Whiteside Mountain.

 
The views start to open up through the trees at the top of this staircase.

First tiny overlook before reaching the top of the ridge. Watch out as there are no protective railings here.

Starting at the westernmost slope of Whiteside Mountain, this trail follows the wooded ridge line of the mountain top to just over a dozen craggy overlooks to its northeastern point, dubbed the Devils Courthouse. While most of the major overlooks are protected by steel cables and railings to keep people from falling off the mountain, there many smaller side trails that lead to unprotected overlooks. Please use your best judgement up here. The farther you go up, the more common the overlooks become. Starring down over the cable railing, you can get a better sense of this mountains magnificent 700 ft sheer cliffs looking south from the second overlook. At over 390 million years old, Whiteside Mountains granite dome was created by molten lava flows deep underground around the same time the Appalachian Mountain chain was being formed. Granite domes are a dime a dozen in the Highlands region and spread all across Western North Carolina and down into Northern Georgia. 

 
Finally some real views from the top of the ridge.

The second major overlook only a few yards away.

This mountain in particular has a special makeup of softer diorite schist and feldspar which make it especially attractive to rock climbers. Whiteside has climbable faces in almost all sun aspects, meaning that a climber can chase shade during summer or sun during winter. You could ice climb on the north side and be in a t-shirt climbing on the south side all in the same day. The area is most known for long multipitch traditional climbs on the southeast face such as the Original Route and Traditions as well as some more difficult testpieces like Warriors Way and Arm and Hammer. There are additional long multipitch routes on the northern tip of the mountain, sometimes extending all the way up to the Devil’s Courthouse. In winter, ice climbers flock to the iconic Starshine, an often thin two pitch ice climb which is only one of 5 popular routes peppered throughout the mountain.

 
This rock marks the actual summit of Whiteside Mountain.

Viewing platform halfway down the ridge near some Peregrine falcon nesting sites. 

Climbing the mountains slope is restricted during certain times of the year to accommodate one of the worlds fastest and most beautiful birds, the Peregrine falcon. One of the best places to see them is from a concrete viewing platform found towards the halfway point on the trail. During the spring and summer, you may see peregrine falcons flying above or sitting on rock outcrops just below many of the overlooks here. Through the endangered species program, the falcon was reintroduced in 1985 to Whiteside Mountain, part of the bird’s native range. From January until summer, peregrines return annually to nest on these rock ledges and feed on the abundant small wildlife that reside within the northern slopes woodland. Known to favor pigeons,  Peregrine falcons mostly feed on birds they have captured in flight including species such as woodpigeons, blackbirds, starlings, small reptiles and bats. Because peregrines are nervous parents, climbing routes near nesting sites are closed during nesting.

 
Last overlook along the trail before reaching the Devils Courthouse.

Just when I think I’ve reached the most awe-inspiring and far reaching overlook on the mountain, I follow the trail to an even better vista up ahead. The last of these overlooks shares its name with two other mountain peaks in the state, Devils Courthouse. Not to be confused with the Devils Courthouse found on the Blue Ridge Parkway, this expansive and flat ridge on Whiteside Mountains northeastern tip was once considered sacred by Cherokee lore. Evolving into what is now more commonly called, the “Judaculla”, tales of the slant-eyed Tsul’kalu, an immense giant who could, among other things, control the weather (his arrows were lightning bolts) centered around Whiteside Mountain and a cave believed to be its home just below the Devils Courthouse. Since the 1980s, the forest service has tried to restrict access to the Courthouse and has allowed the foot trail to it to grow over because of dangers such as strong winds. They also did not want accidents from paragliding and similar activities taking place from the mountain top or from the overlook. There is also an overhang, a small platform less than 7 feet in diameter, connected to Whiteside as if it were a cantilever which resembles other notable ledges like Pickens Nose and McAffee Knob. From this point the trail circles back, begining its slow and leisurely descent to the parking lot along the old roadbed we talked about earlier. 

Quick iPhone shot of Whiteside Mountain from Big Scenic Overlook along U.S. 64.

Up next, we are back on the hunt for some of the more popular waterfalls in the area. Located just a few miles from downtown Highlands, Glen Falls is on the East Fork of Overflow Creek in the scenic Blue Valley area of the Nantahala National Forest. Consisting of three separate waterfalls spread out over along a 400 ft descent, this is one of the bigger waterfalls in the region and a popular tourist attraction during the summer months. Viewed from overlook platforms along a 2.0 mile round trip hike, visitors can opt to either start at the Lower Falls parking area or Upper Falls Parking area within the Glen Falls Scenic Area. Stay tuned for this upcoming adventure and as always, see y’all on the trails!