Adventures in Maui

At first glance, a non-surfing trip to Maui doesn’t seem like it would offer a ton of adventure. You’re surrounded by the newlywed and nearly dead, the island appears to be totally tourism-based, and many people go there to stagnate on the beach.

But then, there’s Haleakala. The massive ~10,000 ft volcano dominates the island, and to my delight, it ensures there’s plenty of adventure for land enthusiasts. These are my top favourite adventures thanks to this amazing volcano…


Exploring waterfalls fed by Haleakala

I thought we had mighty waterfalls in Squamish, but the waterfalls in the southeast and eastern side of Maui were insane. With water flowing 10,000 feet from the top of Haleakala, there are tons of waterfall adventures. One day, we hiked along the Pipiwai Trail at the base of Haleakala, which was beautiful. Taking the questionable advice of another hiker to venture off-trail, we scrambled up a waterfall’s lower pools, and a few minutes later we found ourselves staring up at a private, 300-ft waterfall in the middle of nowhere. (Note this can be super dangerous, due to rocks falling from the waterfall, and sudden flash floods.)



This was super dangerous, in retrospect. I get some adrenaline just looking at this pic of Julien so close to it!

We got super close to the waterfall base for about 30 seconds before beelining back to safety, fearful of watermelon-sized rocks falling from the falls or from the canyon surrounding us. Still, those 30 seconds were incredible. Looking at Strava’s global heatmap off the island’s south/east Hana Road, you can tell there are tons of crazy hikes like this that only a few people do, swim-hiking up waterfall pools. I stayed up late one night reading tons of crazy stories, as these type of hikes often result in rescues, injuries and deaths because flash floods are so sudden, with the water flow from Haleakala at 10,000 ft. suddenly changing. Definitely a lot more adventure than I expected!


Driving the back road to Hana

The Road to Hana is already infamously windy, blind, and rollercoastery. Most people take the northern route from Pa’ia Town, then return the same way they came. If you look though, you can take this interesting back road, on the south side of Haleakala through Kaupo. On the maps they give you at rental car companies, there’s a big asterisk on that section of the road with font in red which says “Do not come between these points. Driving on unauthorized roads violates rental car contracts.” This of course only made us more curious. If they’re telling tourists not to go there, doesn’t that mean it will be way less busy, and more fun? We did some research, checked that there were no landslides or other highway warnings, and decided to go for it.

The road was beautiful, taking us pretty high on the side of Haleakala from Kula, and then back down to sea level near Kaupo, where the road precariously curved around cliffs right next to the ocean. As promised, many corners were totally blind, and in between those, uncut grasses and hills caused stretches of total blindness. We honked the horn sometimes, but thankfully it wasn’t busy, and generally the other drivers were being cautious and chill. It was so fun, like being on a rollercoaster ride. At one point, there was a pullout in the middle of a giant U-shaped curve in the road, which happened to be a black sand beach with a waterfall in the middle. It felt like total paradise. Since this section of the road is often un-advised in many blogs online, it was way less busy than the main road to Hana. Not for everyone, but if you’re up for an adventurous drive, it was tons of fun.

This is what the back road to Hana looks like.

Venturing into the Haleakala crater

Best of all adventures was the Haleakala crater. I got Julien to drop me off at the Halemauu Trailhead which is near 8,000 ft., and then he continued to meet me at the crater summit, which is just over 10,000 ft. From the Halemauu Trailhead, I ran along and then joined the Sliding Sands trail to the top, which made for a super-fun 11-mile trail run. Haleakala is a National Park, plus it’s on every Maui “must do on your trip” list, so I figured it would be busy. Boy was I surprised and delighted! I experienced miles of total wilderness!

Starting at the Halemauu Trailhead, the trail took me down a 400 meter cliff-lined descent down a winding rocky technical trail, which was super slick from the fog and winter rains. It was super fun and intense, and I really had to be cautious because of the combo of slick mud and cliffside. Was not expecting challenging terrain! It felt a bit like running down into the Grand Canyon from the South Rim, it was that special.

The trail descended from that little mountain in the foreground.

From there, the trail traversed a grassy arid area near this beautifully remote-feeling Hōlua Cabin. After the first 3k, I didn’t see a soul! The trail eventually led me deeper and deeper into the crater, with giant sand mountains rising in the misty fog in gray, black and red. Being totally alone in there with the atmosphere of the dark, foggy rain, it felt extremely wild and desolate. It sort of felt like the sand-mountains could suddenly slide and bury me, or that the fog could intensify and cause a whiteout-type situation. It made me feel so small and vulnerable, which was exactly the experience I was craving. I felt excited, like I wanted to run to safety. The run ended in a punishing mostly-runnable climb of about 950 meters at altitude, topping out at the summit close to 10,000 ft. That was tough! I would definitely do that run again, it’s one of my favourites I’ve ever done.

Total wilderness inside the crater.

Next trip, I definitely want to do the same route again, and I also want to try the longer adventure from sea level, up the Kaupo Trail and into the crater. (To get there, it means we get to drive part of the back road to Hana again!)


These adventures surprised me, showing me that there’s a ton of true wilderness to be found and explored in Maui. I can’t wait until the next trip!