Even for Maui locals, the hiking trails of Moloka‘i are shrouded in mystery. Often the trails require either four-wheel drive access or permission from private landowners, although there are still a number that are accessible to the public. You’re rewarded for your effort with sweeping views of the entire island.

Bathed in the scent of eucalyptus and pine, the “topside” of central Moloka‘i is where you truly feel as if you’re in the mountains.

Bathed in the scent of eucalyptus and pine, the “topside” of central Moloka‘i is where you truly feel as if you’re in the mountains. Photo © Dr. Colleen Morgan, licensed Creative Commons Attribution.

Topside Moloka‘i

Bathed in the scent of eucalyptus and pine, the “topside” of central Moloka‘i is where you truly feel as if you’re in the mountains. With trails ranging in elevation from 1,500 to 4,000 feet, the air is cooler up here, and once you enter the Kamakou Preserve, the weather turns wetter and the surroundings lush. Songs of the native i‘iwi birds ring from the treetops while mists hang in the silence of deeply carved valleys.

Kalaupapa Overlook

The easiest walk is the 1,500-foot paved walkway leading to the Kalaupapa Overlook starting at the end of the road in Pala‘au State Park. Take Highway 470 past the mule barn for the Kalaupapa trail rides and continue until it dead-ends in a parking lot. Here you’ll find some basic restrooms but no potable water. Be prepared for high winds that can blow your hat off, and get your camera ready for a view of the Kalaupapa Peninsula which is the best you’re going to find short of actually hiking down there.

Kalaupapa Trail

The Kalaupapa Trail is the most popular hike on Moloka‘i. Descending over 1,700 vertical feet over the course of 3.2 miles and 26 switchbacking turns, this trail was hand-carved into the mountain in 1886 by Portuguese immigrant Manuel Farinha as a way to establish a land connection with the residents living topside. The trail today remains in good shape, although you do need to be physically fit and keep a keen eye out for the “presents” left on the trail by mules. Since this is part of the National Historic Park, reservations are required to tour the peninsula, and those who try to sneak into Kalaupapa could end up facing possible prosecution. Those wanting to hike the trail instead of riding a mule can contact Damien Tours (808/567-6171), which, for the cost of $50/person, will meet hikers at the bottom of the trail at 10am and provide a four-hour guided tour of the Kalaupapa Peninsula. To reach the trailhead, drive 200 yards past the mule barn on Highway 470 and park on the right side of the road.

Pepe‘opae Bog

Constantly shrouded in cloud cover and dripping in every color of green imaginable, if ever there were a place to visualize Hawaii before the arrival of humans, then that spot is the Pepe‘opae Bog. Ninety-eight percent of the plant species here are indigenous to the island of Moloka‘i, and 219 of the species in this preserve are found nowhere else on earth. Following Highway 460 from Kaunakakai, make a right before the bridge at the Homelani Cemetery sign and follow the dirt road for 10 miles all the way to the parking area at Waikolu Overlook. Even making it this far in a two-wheel-drive vehicle requires high clearance and the best road conditions. Trying to go any further will just get you stuck. Those with four-wheel drive can knock 2.6 miles one-way off the journey by continuing to the trailhead, but even this is precarious at best and the driver needs to know what they’re doing behind the wheel.

Look for the signs for Pepe‘opae Bog and follow them. Once the trail begins, it’s imperative you stay on the metal boardwalk. If you accidentally step off, you can expect to sink shin-deep into the soggy moss and mud. The boardwalk runs for 1.5 miles through some of the most pristine rainforest left in the state. Hikers who make it to the end are rewarded with a view into Pelekunu Valley which plunges 4,000 feet through the uninhabited, untouched wilderness below. Hikers are free to attempt the climb on their own, or the Nature Conservancy (808/553-5236) leads hikes into Pepe‘opae once per month, March-October. Make advance reservations.

Pu‘u Kolekole

On the same 4WD road leading to the Pepe‘opae trailhead, hikers who take the fork to the right will instead reach the start of the Pu‘u Kolekole trail. This two-mile trail leads you to the 3,951-foot summit of Pu‘u Kolekole. From here the view overlooks the southern shoreline and fringing reef to offer the best view of southern Moloka‘i.

At Halawa, the trail can only be accessed by going through a local company.

At Halawa, the trail can only be accessed by going through a local company. Photo © Andrew K. Smith, licensed Creative Commons Attribution.

Halawa Valley

At Halawa, the trail can only be accessed by going through a local company and paying to hire a local guide. Bookings to hike into Halawa Valley can be made through either Moloka‘i Outdoors (808/553-4477) or Moloka‘i Fish and Dive (61 Ala Malama Ave., 808/553-5926).

West Moloka‘i

Given the lack of mountains in western Moloka‘i, most of the hikes on this side of the island follow the coastline.


A nice walk from the condo complexes of Kaluakoi is to follow either the coastline or a dusty dirt road to the secluded beauty of Kawakiu Nui Beach. From Maunaloa Highway (Hwy. 460) take the Kalukaoi Road exit and follow it to the bottom of the hill before making a right on Kaka‘ako Road. Finally, a left on Lio Place brings you to the Paniolo Hale parking lot, where you can follow the signs for the beach, crossing over the fairway of the old golf course before you reach the shoreline. Make a right, and 45 minutes of walking along the coastline will bring you to Kawakiu. Or, if the tide or surf is too high to walk along the coastline, turn inland past Make Horse Beach. After a few minutes you’ll meet up with a dirt road which leads north and deposits you at Kawakiu. About 100 yards before the road drops onto the sand at Kawakiu, there’s an ancient Hawaiian heiau out on the rocky point.

East Moloka‘i

Deeply carved down from the 4,961-foot summit of Kamakou, the valleys of eastern Moloka‘i beckon to be explored. Despite being beautiful, forested and laden with waterfalls, many of the valleys are cut off from public use. Liability concerns have forced landowners to restrict access to many valley trails, although some are still available by taking part in a guided tour.

Excerpted from the First Edition of Moon Hawaiian Islands.