Kalaupapa Trail: A Beautiful and Historic Trail on Moloka'i

Moloka'i Sea Cliffs on Kalaupapa Peninsula

This part-tour, part self-guided hike combines stunning scenery with deep historical significance. On this unique Molokaʻi adventure, you’ll descend 26 switchbacks along the island’s dramatic north coast and arrive at the Kalaupapa Settlement—a preserved community originally established for individuals with Hansen’s disease (leprosy). The journey ends with a panoramic view of Molokaʻi’s towering sea cliffs before heading back up the switchbacks. Whether it’s the beauty or the historical gravity of the place, there’s something unforgettable about this trek.

Note: As of writing, tours and trail access to Kalaupapa are suspended indefinitely. Check the National Park page for the latest information. Currently, there is no legal way to access this trail.

Trail Info

Trailhead Name	Kalaupapa Trail
Distance	7 miles / 11.3 km (out and back)
Estimated time	7-8 hours (including tour)
Elevation gain	1,600 ft / 500 m
Highest point	1,600 ft / 500 m (Start of trail)
Permits / fees	Yes — requires a paid tour
Parking	Paved lot
Toilets?	Trailhead and at Kalaupapa Settlement
Dog friendly?	No (prohibited)

Know before you go

Tours are required. Although the trail itself is self-guided, access is only granted if you’re booked on an official tour. These typically include hikers, mule riders, and folks flying into the peninsula. Tours used to be booked through Father Damien Tours (currently suspended).

Tour Options (as of 2019):

Tour Type	Cost*
Self-guided hike	$100
Guided mule ride	$200
Fly-in from topside	$300

*Prices are outdated and will likely change when/if the tours restart.

The Trail

Check-in starts early, around 8 a.m. After checking in at the Mule Barn, signing a few forms, and getting a safety briefing, it’s time to hit the trail.

But first, a couple of worthy detours near the trailhead. Just a few minutes down the road, you’ll find two unique landmarks. First up: Phallic Rock. Let’s be honest, if you’ve traveled enough, you’ve probably seen a few suggestive rock formations. But this one? The resemblance is... unmistakable.

uvenile giggles aside, this rock, known as Kaule o Nanahoa, has a place of cultural significance. Known as the Fertility Rock, local women have brought offerings and prayers here for generations, hoping to conceive. Some even spend the night.

The second nearby landmark is the Kalaupapa Lookout. From here, you’ll get a striking preview of your destination—the peninsula far below, surrounded by ocean on three sides and hemmed in by Molokaʻi’s massive cliffs. Let’s go get down there.

Once you enter the trailhead, it starts off relatively flat. But soon enough, the 26 switchbacks begin, zigzagging their way down toward sea level. The footing is uneven in places, but manageable. It’s the return trip that’s the real workout. Be sure to turn around now and then to appreciate the view as you descend.

The downhill section goes by surprisingly fast, so take your time and soak in the coastline. Those cliffs are jaw-dropping.

At sea level, the trail continues along a clear path just above the beach toward the Kalaupapa Settlement. Important note: during our tour briefing, we were told that going onto the beach is prohibited, so sadly, no mid-hike swims.

Eventually you’ll reach a large open field with some bleachers. This is the meeting point for hikers, mule riders, and fly-in visitors. Time to shift gears from solo hiking to guided exploring.

The next part of the journey is by bus. You’ll be driven around the settlement, stopping at different historical and cultural sites. I won’t spoil all the details here, but it’s a moving and informative look at the people who lived here and the efforts to preserve this community.

he highlight for me? The stop at the sea cliff overlook on the far side of the peninsula. Did you know Molokaʻi is home to the tallest sea cliffs in the world? From here, you’ll see exactly what that means. Unless you’ve got a boat or plane, this is one of the only ways to witness them up close. It’s a powerful, almost humbling sight.

One last photo, and it’s back on the bus to return to the trailhead. And yes, you’ll hike up all 26 switchbacks back to the top. One more leg of the journey before calling it a day.

SS Reflections

Unless you live in Hawaiʻi or are determined to visit every island, Molokaʻi may not be high on your list. With less tourist infrastructure and fewer attractions than its sister islands, it’s easy to see why.

But if you do make it to the Friendly Isle, this hike should be on your radar. Kalaupapa is a rare place. It is rich in history, deeply human, and stunningly beautiful. It feels untouched, preserved in a way few other places in Hawaiʻi are.

That mix of isolation, meaning, and scenery is what made this adventure truly special for me.

Other helpful resources

Trailing Away's writeup of this hike
Official Kalaupapa NPS page with details and updates about the area