Hiking That Feels Like Home
For San Francisco based hiker Hugo Allen, better known as The All Day Hiker, an “ideal” hike isn’t about the biggest peak or the longest day. Instead, it’s about returning to Oʻahu, his old stomping grounds.
His trail of choice? Mt. Kaʻala, a strenuous climb that doesn’t even need to end at the summit. For Hugo, it’s enough to get high above the rainforest, soaking in endless green, reddish dirt, and the Pacific horizon. The essentials? A quiet spot, a hardcover book tucked into a makeshift brown-bag bookcover, and a little nostalgia.
Mt. Kaʻala: a hike that reads like a memory
Ask Hugo for his ideal hike and you won’t get a summit checklist. You’ll get a postcard.
“It’s a strenuous hike, but I wouldn’t need to finish it. I’ll get somewhere high enough to enjoy the solitude, with the tropical rainforest and its never-ending greenery with reddish dirt, and the horizon overlooking Waiʻanae and the Pacific ocean. I’d bring a hardcover book in a makeshift brown-bag cover, like old times from school. Blissfully stubborn nostalgia.”
That line “blissfully stubborn nostalgia” nails the difference between adventure performed for an audience and adventure lived as a refuge. For Hugo, the trail is a place to remember who he was and who he wants to be, with no algorithm to please.
The trail taught him humility (and how to notice)
Hugo’s biggest lessons come from scarcity and small kindnesses. He remembers a hike when water ran frighteningly low and he had to slow to a crawl, rationing every sip. A stranger offered half a litre, enough to finish the route and make it back to camp.
“A hiker gave me half a liter of water, enough to finish my hike. That reminded me of the goodness in people.”
It’s the type of moment that reshapes behavior off-trail: he’s more attentive to people’s tiny signals now, the same way he reads subtle cues from the forest, a sudden avian lift, a silence where wind should be. Those quiet observations translate into everyday empathy.
Weather, DNFs, and the humility of being underprepared
Experience doesn’t mean invincibility. Hugo doesn’t romanticize DNFs; he owns them.
“DNF on account of the weather, and I wasn’t appropriately dressed for it… Getting caught underprepared is humbling because nature won’t be bending to my shortcuts.”
That honesty matters. It’s a reminder that lightpacks and “minimalist” flexes are only useful when the basics are respected: extra layer, headlamp, water filter. Hugo’s pack is his ‘backpacker cosplay’ essential gear fused with identity, but he’ll never gamble on the non-negotiables.
What he shares (and what he keeps quiet)
Hugo draws a line between what the public sees and what he keeps for himself. He cuts certain footage because it makes him self-conscious; he avoids public callouts that would only inflame trail politics. But when he does speak up, he does it with intention.
“Sometimes that means calling out tone police adjacent attitudes when hikers shame others for carrying safety gear or talking honestly about poop logistics.”
That blunt, funny honesty part heart, part trail-counsel gives his content weight. He’s not content with performative humility; he wants useful conversations: safety without shaming, care without virtue signalling.
A story never posted: recklessness that becomes your risk
There’s a memory Hugo hasn’t shared online: scrambling at night with someone dangerously impaired. He remembers yelling “I’m slipping,” and the other person, high out of their mind, mumbling. The panic was real, the responsibility shared.
“That moment tied into how someone else’s impairment can become your risk, too.”
It’s not moralizing. It’s a recognition that trail culture contains contradictions: people escape into nature, sometimes recklessly. Those moments stay with you and ask uncomfortable questions about responsibility.
What’s Next: Half Dome Awaits
This September, Hugo is setting his sights on one of Yosemite’s most iconic challenges: Half Dome. Equal parts excitement and nerves fuel his upcoming climb.
“Both excited and nervous,” he admits. “Yeeeeee! …and yaaaayyyy!”
Half Dome is a bucket-list goal for countless hikers, but for Hugo, it’s just another step in the lifelong rhythm of testing limits, finding humility, and laughing along the way.
Why We Love Hugo’s Story
Hugo isn’t telling you to summit everything. He’s reminding us to notice the in-between: the water passed between strangers, the slow steps when energy thins, the humor that keeps us human. At Wyld Peak, those stories sit next to big expeditions and legendary explorers because courage has many sizes. Sometimes it’s a life lived on the trail with honesty, humility, and a brown-bag covered book.
Related reads:
🔹 Percy Fawcett: The Lost Explorer Who Inspired Legends
🔹 Ernest Shackleton: Endurance and the Power of Leadership
Want more Hugo? Follow him at @thealldayhiker, and if his story struck you, share the hike that feels like home in the comments.
Planning your own Half Dome or California adventure? Check out our hiking safety checklists and gear-ready patches to keep your pack light, practical, and personal.