The objective? Get to the summit of Haleakala (10,000 ft / 3,048 m) from sea level.
My journey begins some 63 mi / 101 km from the trailhead in Kaupo (located on the far east side of Maui), and I estimate it will take me two days to get there on foot. I think I will try my luck at hitchhiking.
For those who know nothing of Maui’s geography here is a crash course: Maui is composed of two volcanoes, connected by an isthmus – Haleakala in the east, and Mauna Kahalawai in the west. The town of Hana is the main attraction in East Maui, and is accessible via a long and winding coastal “highway” (the act of driving the road is a tourist attraction in itself).
This is the road I need to follow to the trailhead.

The sun is not up yet, but if I am going to end up walking the entire way I want plenty of daylight to do so. I expect that the traffic headed to Hana will be mostly tourists, and so I am thinking a hitch to take some time (nobody wants a strange man ruining their scenic coastal drive).
Today is Saturday (good for traffic), but it is also overcast with intermittent rain (not good for traffic).
I make my way through the town of Makawao, and continue down the road until the sidewalk shrinks into a shoulder, and the shoulder shrinks into nothingness. The road turns every which way, and practically every corner is blind. Getting hit by a car would be a terrible inconvenience (but possibly a good shot at a ride?).
After a few miles of treacherous road walking the morning’s drizzle becomes steadier and heavier – time to equip rain gear. I suit up and decide to try my luck at a few cars (perhaps I will be pitied in the rain?). Fifteen minutes and only three cars later I conclude I am not on the best road for hitching. I continue walking.
As I walk, I hear a car approaching from behind me. As I step to the opposite side of the road to avoid being run over, I lazily stick out my thumb and continue to walk without turning to face the driver. I am shocked when a large truck pulls to a stop in front of me. Huzaa!

I toss my pack in the back, hop in the passenger seat, and meet Mike, a Hawaiian home builder heading towards Hana for work. Turns out that Mike drives the road to Hana almost daily, and he is an expert as navigating its twists and turns (aka he is a madman behind the wheel).
We barrel down the road, passing every tour van and rental car failing to yield to Mike’s massive truck. Despite the road being wet from rain and our driving taking place primarily on the wrong side of the road, I feel oddly safe in the care of Mr. Mike. Much faster than I could have guessed, I am already halfway to Hana.
However, Mike has business further back, and he brought me to the halfway point as a courtesy (there is a small parking lot, convenience stand, and benches here).
“You have a knife?” Mike asks.
“Nope, couldn’t carry it onto the plane.”
“Here, I have some extra machetes. Take one, you are going to need it,” he tells me.
Although confident that I will not be needing a five-pound machete, I decide to take it anyways. How am I going to turn down a giant machete? Maybe I will get to do battle with a wild boar in the jungle. I hope this doesn’t hurt my chances of getting another ride.
I thank Mike for all his help and step out into the rain once more.

Here the cars are more frequent, but sadly, so is the rejection (I swear, this machete is to be used only for good).
After about an hour I am still without a ride, and it begins pouring rain. I buy some chips, drink some water, and take shelter under a leaky thatched roof. Every car that passes I see as missed ride opportunity, but it is still early and I am already farther than anticipated. I leisurely eat my chips and wait for the rain to let up.
Resuming ride solicitation and growing increasingly impatient I begin experimenting with new strategies. Dancing, waving, singing, winking, feigning injury, anything to get drivers’ attention. I consider walking, but am legitimately afraid of being hit by a vehicle. Hitchhiking requires patience, and so I remain on the shoulder with my thumb in the air.
Eventually a vacationing couple from San Francisco pulls up and invites me into their car. They are driving around the entire island, and so not only will they get me to Hana (the town that most people turn around in), but they will also get me all the way to Kaupo (where the trailhead is).
Rob and Emily (a fellow writer of words on the internet – check her out at EmilyStyle) turned out to be fantastic companions. Along the Hana Highway we made stops at the Kahanu Garden, in the town of Hana for lunch, and even took a 4 mi / 6.4 km hike down the island’s Seven Sacred Pools trail for some waterfall action.


Past Hana the road becomes narrow and unpaved in places. Rental car companies discourage (or even prohibit) renters from driving their cars past Hana, but I say go for it (but you should definitely never listen to anything I tell you).
We slowly make our way over the Hana Highway’s many bridges, and before long we arrive at the Kaupo General Store. It is now almost five o’clock. My companions drop me off and continue their adventure around Maui, short a hitchhiker.
I head into the store to find out how ridiculously priced their beer is. At two dollars a bottle I am happy with what I find. I buy myself some much-needed beverages and candy bars.


Making myself comfortable on the porch I hear a terrible clicking noise coming from down the road. The noise draws closer and soon I can see a minivan limping its way down the road. The wounded van pulls up in front of the store and is joined by two other cars.
A large family from Illinois emerges from the cars, and long story short: they stand around for almost three hours attempting to find a tow (why they didn’t just leave one person with the broken car, I do not know).
Turns out that a tow costs $500 and they ultimately decide to just leave the car. I guess they should have listened to the rental car company.

The store’s owner tells me that I can sleep in front of the store, and invites me to hang out with the employees and neighbors as they drink and smoke on the porch.
A few hours after dark everyone heads home. I make my bed on the porch as the owner takes what feels like an hour to close up shop. Eventually she bids me goodnight and leaves me to sleep. I finally doze.
My slumber is short-lived. I am soon awoken by someone coming up onto the porch. I look up and see a child with a flashlight. They do not notice me, and I say nothing to alert them to my presence. What they are doing? I have no idea.
I close my eyes and ignore them, but am soon startled by a terrified scream and the sound of footsteps fleeing the scene. Guess they saw me.
“Sorry” they yell from afar.
“That’s alright,” I lie, as I once again drift off dreamland.
Apparently this kid was not sorry, because now, fully aware that I am sleeping on the porch, he proceeds to set off fireworks in the parking lot with his dad and a friend. This goes on for literally almost two hours.
Am I being intentionally tortured? Is this retribution for my scaring them? I should have just walked a mile down the road and slept on the peninsula jutting out into the ocean. The spectacle eventually comes to a close, and again, I slowly find sleep.

But what’s this?
A rumbling noise approaching the store, and soon a car pulling into the parking space in front of me. A tow truck is here to rescue the abandoned minivan. Fantastic. I am no towing expert, but these guys take an incredibly long time to get this car out of here. A solid forty minutes at least. However, they do an amazing job of being extra loud throughout the entire process.
I have no idea what time it is, but I am certain that I will not be getting as much sleep as I would like to have before my hike tomorrow morning.
Now, finally, mosquitos humming in my ears, I can, and finally do, fall asleep and stay asleep.
THE FUTURE: Haleakala Day 2: Up The Kaupo Gap Trail
THE FUTURER: Haleakala Day 3: Sliding Sands, Summits, & Swiss