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Kalaupapa Trail-- A beautiful and historic trail on Moloka'i

Updated: May 27

Moloka'i Sea Cliffs on Kalaupapa Peninsula

This part tour/part self-guided hike combines beauty with history in a unique adventure on Moloaka'i, one of Hawaii's least visited islands. Descend twenty-six switchbacks along the gorgeous coastline, arriving at the the preserved Kalaupapa Settlement, a place originally established by King Kamehameha for Hawaiians with Hansen's ("lepur") disease. Finish your tour with a view of Moloka'i's northern sea cliffs, before climbing up those beautiful swtichbacks one more time. Whether it is the history lesson or the beauty of the area, there's sure to be something to interest or excite you on this journey.

Note that as of writing this, tours to the Kalaupapa Settlement and access to the trail are suspended until further notice. This National Park page provides the most up to date information of when tours may resume. As of now, there is no legal way to access this trail.


Trail Info

Kalaupapa Trail Hike Information Table

Know before you go

  • **Accessing this trail requires you to join a tour. While it is a "self-guided" hike you are required to meet a tour group at the Kalaupapa Settlement where you will meet with other hikers, mule-riders, or people who flew directly to the peninsula. Tours can be booked through Father Damien Tours website.

The different tour options

There are three different ways to get to Kalaupapa, with costs outlined below:

Kalaupapa Tour Options Table

*Note these numbers are based on 2019, before the tours were suspended. The costs will almost certainly change if the tours are restarted.


The Trail

Check in for tours starts early, around 8am. After checking in at the Mule Barn, signing some paperwork, and getting a trail briefing, it's hiking time.

Phallic Rock on Molokai

But first, a quick detour. I have to highlight a few of the other sights in the area. A few minutes on the road past the start of the trail are two additional landmarks worth visiting. The first is the aptly named Phallic Rock. If you go to enough places with rock formations, you'll realize that the obsession with phalluses spans cultures and time. However, the features of this particular phallus were more defined than anything I've seen.

And if you can ignore the 12 year old giggling in your head, this rock does have a place of significance in Hawaiian culture. It is known as Kaule o Nanahoa, or the Fertility Rock, where women who want conceive bring offerings, pray, and spend the night.

Kalaupapa Lookout on Molokai

The other landmark nearby is the Kalaupapa Lookout. This will give you a preview of where we are going. The settlement is down there on the peninsula. So let's get down there.

Kalaupapa Trail on Molokai

After entering the trailhead and following a level trail for a bit, you will begin the twenty-six switchbacks that will take you down to sea level. The footing on this trail is a bit uneven, but overall the terrain is tame--it's the hike back up that gets hard. So on that ascent just turn around every so often to admire this stunning view.

Kalaupapa Trail on Molokai

Given that it's all downhill, the descent seems to fly by. So take your time and admire some of those cliffs.

Kalaupapa Trail on Molokai

Once you get to sea level, the trail follows an obvious path along the beach that will lead you to the settlement and the meetup point. Note, during my tour we were told during our pre-hike briefing that going on the beach is prohibited. That means no mid-hike swims unfortunately.

Kalaupapa Peninsula on Molokai

The trail leads to a wide open field where you will see some bleachers that serve as the meetup point. This is where hikers, mule riders, and individuals flying in will meet up to begin part two of the adventure.

Kalaupapa Peninsula on Molokai

From here, the adventure turns into a more traditional tour. You will load up into a bus and be driven to various sites around the settlement. I won't get into the details, but it was interesting to hear the history of why this place exists and how it has been preserved for so many years.

Moloka'i Sea Cliffs on Kalaupapa Peninsula

The highlight of the tour, in my opinion, is when you are taken to the far side of the peninsula to get a view of the gorgeous sea cliffs. Did you know that Moloka'i is home to the largest sea cliffs in the world? Standing at this point looking out, you can see exactly what "tallest in the world" means. And unless you have a boat or plane, there's no other way to really see these cliffs. This really is a special place.

Moloka'i Sea Cliffs on Kalaupapa Peninsula

And with one more pic, it was time to load up on the bus, so I could hike all 26 of those switchbacks back to my car to continue on my Moloka'i adventure.


SS Hot Takes

Unless you live in Hawaii or are make it a goal to see every accessible island, it is unlikely visiting Moloka'i will make it on your radar. There's so much beauty on each of the islands, and with only so much time (and money) we have to prioritize where to visit. Given the tourist infrastructure and sheer volume of activities on islands like Maui, the Big Island, Oahu, and Kaua'i, it makes sense that those should be first.

But if you do get the chance to make it to the "Friendly Isle", this activity should make the list. It's amazing to see something with such rich history and so beautiful in a preserved place that so few others have set foot on. To me, that's what makes this adventure truly special.

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DISCLAIMER: This website is for entertainment purposes only. The web designer and contributors are not liable for any injuries, accidents, or damages resulting from the use of information provided. Trail data, including trail statistics such as mileage and difficulty ratings, are provided as estimates based on the best available data at the time of publication and may not be 100% accurate. Conditions on trails can change; users should verify information with local authorities or  other reliable sources before embarking on any hiking or outdoor adventure. Hiking is a high-risk activity; individuals should know their limits, take precautions, and prioritize safety. By using this site, you acknowledge and accept these risks; the web designer and contributors are not legally responsible for any consequences.

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