Arriving into the Kaupo area, you will notice how the tropical vegetation stops and the landscape becomes barren and dry. Here Haleakala’s rain shadow creates an environment of yellow grassland, dotted with volcanic rock. Almost immediately after leaving Kaupo village the dirt road becomes a beaten up, potholed, patchwork of driving treachery that meanders along the coastline far below. It is a completely opposite experience from our journey on the road to Hana along the northern coast. Most car rental companies forbid you to take their rentals down this route and in the past it has been closed due to problems maintaining the road as it is subject to landslides and other natural occurrences.
The Kaupo Store
The Kaupo store is found on the south end of Kaupo along the road towards Kula. The quaint little store has a variety of little snacks, drinks and antiques. The locals invite you to sit on the porch and listen to them “talk story”. Here you can feel time slowing down and the Paniolo, (cowboy), past comes alive when locals ride up and hitch their horse to the post out in front of the store.
Kaupo Trail & Gap
The area has a long history which is told in Hawaiian mythology. The plants and trees all have a story similar to those of ancient Greece. Legends told among the old Hawaiians living in Kaupo center around superstitions about the practice of throwing babies umbilical cords into the bottomless pit up at Haleakala crater. It was said that tossing the cord into the pit would make the child strong, but if the parents abstained from the ritual then the child would be prone to thievery. Getting to the bottomless pit entails following the steep Kaupo Trail up through the gap and into the center of Haleakala crater.
The bottomless pit is said to drop all the way down to ocean level, but it seems to be only 60 to 70 feet deep when looking down into it. During times of volcanic activity it functions as a vent for gas, and possibly lava, similar to vents on Mauna Loa or Kilauea.
The Kaupo Trail is very different than the Oheo Gulch hike. Kaupo’s very steep trail does not have the same lushness, waterfalls or swimming spots found at the Pools at Oheo Gulch . The Kaupo Trail meets up with other trails once in the crater and is quite exposed. Going up into the gap is a tough climb, so most people choose to start at the summit and travel their way down. It takes a good two days to complete the full hike. There are cabins available in the crater but you’ll need to book those well in advance. The hike takes you through a Koa forest and has spectacular views when looking towards the Big Island.
The Kaupo Gap is seen high up on Haleakala. Many people believe it was caused by a volcanic eruption similar to what happened at Mount St. Helens in Washington but really this was mother nature at work using her wind and rain. Erosion caused this gap in the crater wall. It is also home to a small moth which only lives up in the gap at about the 3,400 foot level. They feed on live lichens, which grow on the rocks.
Kaupo, Maui section of our island tour shows that Maui is also very desert-like and similar to some western regions of the mainland USA. The Kaupo area has historically been used for cattle farming and still is today. Often you need to be careful of cattle wandering onto the road, especially when driving at night. Kaupo is unspoiled Paniolo, “cowboy”, country in it’s original state. You can easily imagine the Paniolos roaming these wild and windy ranges.
Kaupo’s wind, because it is exposed to the trade winds coming out of the northeast, is perhaps the strongest and most consistent on Maui. It is certainly worth a stop to get out and stretch your legs, but more so just to feel the wind and experience the raw environment of the east slopes of Haleakala while on your tour back from Hana.














