We DO NOT recommend hitchhiking—Just had to get that piece of advice out of the way.
Thumbing a ride is a mode of transportation that has slipped into legend for most places in the U.S. While we know plenty of people that successfully got around without much incident in years past, (back int he 1900s as our kids refer to it), hitchhiking is generally considered too risky to attempt in the modern era. Besides, in a world with ride share services like Uber and Lyft, it really takes the guess work out whether you’ll be picked up or not. (Though we’re told that was always part of the adventure.)
The Islands of Hawai‘i are a place that is just rural enough, just small enough, and just friendly enough, that you may still encounter hitchhikers. At least in some areas, such as the more laid-back, surfer and farming communities. But even in the place that invented Aloha, you should think twice about stopping to pick up a hitchhiker. An old legend on Maui gives warning of why you should be wary of stopping for hitchhikers along a certain stretch of the island.
Highway 30 on Maui is a modern, two-lane highway. In the old days (which anthropologists define as any time before TVs had remote controls) there was a narrow, winding road along West Maui. Parts are still visible in places, such as near the tunnel on Highway 30. It’s possible to awkwardly scramble up to the old road and walk along it (if you’re so inclined). You get an idea of how something as “permanent” as a road can be quickly consumed by nature, even on this dry side of the island. This part of West Maui is called the Pali (cliffs) and soon gives way to a shoreline highway.
In ancient times there was a legendary female robber named Kaiaupe. She would lure men to get friendly with her at the edge of the pali, then kick them over the cliff and rifle their body for valuables (a practice that was named Ka-ai-a-Kaiaupe in her honor). So if you see a woman hitchhiker with a big K embroidered on her clothes… you might want to pass.
While we hope you don’t run into Kaiaupe, you can explore the roadway she is said to have frequented by hiking the Lahaina Pali Trail. This trail starts near Ma‘alaea and ends at Ukumehame Beach, with views of the central valley and offshore islands being the highlight of the trek. It follows part of the historic road that was used even before the old road seen next to the highway. It’s hot, dry and zig-zagging switch backs make this one of Maui’s more strenuous hikes. Be sure to start early and bring plenty of water.
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