Trail Stories - Will Roquemore

About the Guest Will Roquemore — trail name Last Strap — is a fourth-generation Idahoan, PCT class of 2025 finisher, part-time Arizona Trail hiker, and full-time nomad living in a converted 2016 Toyota Prius V wagon. He has been on the road since 2020, produces hiking content on his YouTube channel Sucker for Side Quests, and is currently based in Boise, Idaho, editing his PCT footage and spending time with family. He hiked the first 50 miles of the Arizona Trail in March before tapping out due to record heat and a body not yet recovered from the PCT. Episode Highlights The Trail Name Last Strap is a pre-trail name given to Will by his longtime backpacking friend Chris, who instituted the rule after watching Will fail to leave camp on too many occasions due to having too much fun before the pack was packed. The rule: no extracurricular fun until the last strap is fastened. The name was already established among his Idaho and Colorado crew before the PCT. He considered getting a new one. Nobody else has it. He kept it. The Prius — A Philosophy of Freedom During COVID, Last Strap was renting cars to drive between Colorado Springs and Boise to see family. He rabbit-holed into the Prius nomad YouTube community, found a 2016 Toyota Prius V wagon — the station wagon model, only made for three years — and bought it. When his landlord raised the rent during lockdown, a friend asked why he needed all his stuff anyway. He sold it, gave it away, donated it, or threw it away until everything he owned fit in the Prius. He quotes Fight Club: the things you own end up owning you. He cannot stop using the word freedom. The Prius forces the discipline and provides the mobility — including great gas mileage that makes cross-country drives cost $90 instead of $800. Origin Story — Jimmy Smith Lake Last Strap grew up fishing and camping in Idaho with a mother who took her kids outdoors before they could walk. In his late 20s he hiked to Trinity Lakes with a friend, kept going alone when she turned back, and knew immediately he had found his thing. He and his bass player Chris drove through the night after a metal concert, hiked into a snowstorm at 2 a.m., set up tents in a field of cow pies, got a fire going — and the saturated rocks started exploding and shooting hot shrapnel at them. They stayed, caught fish, ate them on the mountain, and have been close friends ever since. Chris later became the world's best PCT resupplier. Getting to the PCT Last Strap heard about the PCT in the early 2000s and immediately classified it as impossible for him. He kept backpacking for years. About five years ago a retinal detachment and subsequent surgery led to a hard year of mental health recovery. His partner at the time encouraged him to look into actually doing the PCT. He kept refreshing the permit system until he got one. Once the permit was real, the hike was real. Legendary Mode — The Breakup Last Strap's biggest fear going into the PCT was something bad happening to someone he loved — especially his partner of two years. She broke up with him five days in. He hiked the remaining 2,650 miles broken-hearted, not sleeping, not eating, rage-hiking 20-mile days before he had trail legs, losing approximately 20 pounds by Idyllwild. He calls it hiking on legendary mode. He is grateful to every member of his early tramily who gave him space to trauma dump and overshare — without them, he could not have finished. Shout out Drizzle. The Hot Take — Thru-Hiking Is Not Therapy Last Strap's counterintuitive position: thru-hiking is not a healthy place to process trauma. Miles of solo processing produced assumptions rather than insight. He didn't have the tools to ask himself the right questions. The emotions festered. It was professional therapy after the trail that actually helped. He is not saying don't go — he believes nature heals in many ways — but he would not expect a thru-hike alone to fix what professional help is needed for. Doc notes this sits in direct contrast with many Dark Miles guests. Last Strap acknowledges it is a hot take. The Best Hitch — Gunner the Chihuahua Near Trout Lake on the PCT, Last Strap flagged down a logging semi with a handmade sign reading Hiker to Town. The driver — described as super hillbilly, with a Don't Tread On Me hat on the dash and a deep Southern accent — had a Chihuahua named Gunner in his lap. Last Strap got in, pulled out his GoPro, did a little interview, and made the driver take a photo with him in the cab. He considers it one of the great hitches of his life. He thinks the driver regretted it, if anything, because of the smell. Dad Strap — Harts Pass Last Strap and his father have not had a particularly close relationship in their adult lives. Hi