Trip report by site editor Rick McCharles.
I did an unpopular route listed in Maui Trails by Kathy Morey, but not in any other hiking guidebook.
She calls this the “Kaupo to Halekala Park Boundary“, an awkward moniker it seemed to me.

A far more common use of this trail is as the Kaupo Gap exit from the volcanic crater above. I was walking it backwards, uphill rather than downhill.
On the bright side, it’s well signed.
I suspect many hikers in the past arrived at remote Kaupō Ranch in rough shape from the 6000ft+ descent.
From GORP:
… Kaupo Trail can be an experience in misery: blistered feet, tortured knees, intense sun or torrential rain, and no available drinking water. The steep, rocky terrain in Kaupo Gap makes it essential that you be in good physical condition. Weak knees, bad backs, and new boots are not compatible with this trail. …
Actually, crossing a working cattle ranch was interesting.
Wild pigs are a bit of a pest. I saw many.

Here’s a working trap, set to capture the bacon.
I stepped on over ripe avocados.
There were no signs any other hikers had ever been on this trail. Only myself, a few farm hands, and these onlookers.
Views back to the wild Kahikinui coast were nice.
But for me the biggest attraction of this walk was that it felt an authentic Hawaiian experience, not a standard tourist cattle trail.
I recommend it.
See the rest of my Kaupo to Halekala Park Boundary pics.







As a twenty year old in 74′ I spent Halloween night in the 8 sided observatory on Haleakala’s rim. At sunrise the next morning I walked down Sliding Sands trail & across the floor of the crater in a matter of a few hours. That was a descent of about 3000 ft. – approximately 7 miles long. The next 11 miles were grueling. About 8 miles down hill I found myself grabbing my knees to keep them from knocking & setting goals like the next major bend or large tree. I was carrying a thirty pound pack, little water & then I lost the trail in a broad pasture. Luckily for me the local rancher allowed me to pass through his property using his driveway while keeping his pitbull at bay. Needless to say, I slept like a baby that night on Nick Soon’s porch, aka Kaupo Store. The next morning I could barely walk but the experience, pictures & memories of that epic hike I’ll cherish always.
Aloha,
Mike