Pali High
Hoofing it up Kealaloloa Ridge, we hike the winding pali trail and rediscover Maui’s past along the way.
Ashley Stepanek
Photography by Jason Moore | Forest & Kim Starr
To a Dance Twenty-five Miles Away
By postmaster of Lahaina Arthur Waal, 1898
Bright and early, alone and on horseback, I left Lahaina on a Friday morning, December 16, 1898, for a twenty-five-mile ride to Wailuku at the invitation of friends to attend a dance on Saturday night at the K.P. Hall. . . .
Passing the first flat and windy Olowalu plains at eight o’clock we commenced to ascend the steep and narrow mountain road. . . . From here we climbed over the ancient trail that wound snakelike up and down over the rocky precipices [in some places offering] a five-hundred-foot drop directly into the sea. Fortunately, Manuel de Rega had given me one of his best saddle horses. . . . a sure footer to carry me safely up and down these weather beaten and windswept regions. I did not know the road, but my faithful horse did. I simply followed him on his back. We never met another horseback rider, but ahead of me were several slow moving cows going my way that would not move out of the trail or cow patch to permit me to pass.
This horse had carried the mails twice a week for a man who delivered the mails to another man on horseback at half way on the mountain between Lahaina and Wailuku. Here the mail pouches were exchanged, the Lahaina pouch to Wailuku and via verse.
At eleven o’clock we arrived at Ma‘alaea Bay, known as McGregor’s Landing. This place has a small shelter and was a station for passengers awaiting the arrival and departure of steamers. Here I gave my horse a two-hours rest, food and water. A sandwich with a layer of ham and eggs and a bottle of Wadsworth’s soda water satisfied me. We were only seven miles from Wailuku where we arrived at three o’clock. I do not know which one of us was more tired, the horse, or I. . . .
My friends when issuing the invitation did not expect that I had sufficient courage to venture a horseback ride of twenty-five miles over an old ancient, rough mountain trail just for a dance. But I did it!
If Waal’s story is any indication, the Lahaina Pali Trail’s undulating, switchback curves and uneven, rocky slopes haven’t changed much in the last hundred years. The trail fell out of use in 1900 when prison laborers constructed a one-way dirt road for carriages along the base of the pali (cliff). Eleven years later, a three-ton truck was the first vehicle to negotiate that lower road—and met 115 scary hairpin turns along the way. The road was widened and straightened several times until 1951, when the Honoapi‘ilani Highway and tunnel were built as a permanent alternative.
But you can still experience the ol’ pali trail the same way Waal did. The only difference? Hiking instead of horseback riding. And you do it purely for fun. Looking for an adventure one Friday afternoon, some friends and I decide to suit up our hiking boots, smear on the sunscreen, and tug on our trucker hats for the trek.
“It’s interesting to think about what Native Hawaiians wore when they hiked the pali some 200 ago,” I say, driving. “I imagine they had much less on.” Clad in loose kapa (bark cloth), with only woven ti leaf sandals or their bare feet, they used the pali to travel from one ahupua‘a (land division) to the next as part of the alaloa (long road), or King’s Trail that once circled Maui. Hawaiian tradition says it was built during the time of the ali‘i (chief) Kiha-a-Pi‘ilani, who ruled the island about 400 years ago. Back then people traveled along the coast where it was passable, and swam around sea cliffs where it was not.
The pali is a monument to both the ancient Hawaiians’ and Waal’s way of life, but time and automotive technology have contributed to obscuring it, making the trail fairly hard to find unless you know where it’s at. To complicate matters, we wanted to hike it backwards, to experience the magic of an orangey sunset as we descended the slope of Kealaloloa Ridge, the southern shoulder of the West Maui Mountains.
