Chasing the Calendar Year Triple Crown
Meet Connor "Jackrabbit" — an ambitious thruhiker taking on America’s three longest trails in one calendar year. We’re following his journey.
Connor Chapdelaine (he/him)Naperville, ILAT Class of 2021, PCT Class of 2022@jackrabbithikes
"Jackrabbit" is no stranger to taking challenges head-on. An avid ultrarunner and thruhiker, he’s competed (and succeeded) in big-name races and trails—from placing 26th in The Javelina Jundred on the heels of seasoned pros in 2023 to setting the Fastest Known Time (FKT) of Eagle Rock Loop in Arkansas in four and a half hours in 2025.
IfeelthemostawakeandawarewhenI'mhiking.
Going after the unknown, especially when that unknown is hidden deep in the remote wilderness, comes second nature. "It's like this natural progression of seeing what's possible, seeing what you can do," explains Jackrabbit, who earned his trail name hiking the Appalachian Trail in 2021.
This year, he’s eyeing a monumental feat—completion of a Calendar Year Triple Crown (CYTC)—which requires hiking the Appalachian Trail (AT), Pacific Crest Trail (PCT), and Continental Divide Trail (CDT) all within one calendar year. And he’ll attempt to do so in record time.
The nearly 8,000-mile route follows America's most iconic long-distance trails. Starting April 22nd, he'll embark northbound on the PCT before transferring to the CDT, and ending with the AT. He will need to average nearly 33 miles daily to attempt the fastest known time (FKT), which is currently 233 days. Doing so, he’ll cross over the finish line near December 8th, 2025.
Jackrabbit hopes to claim this FKT title as his own.
Calendar Year Triple Crown Itinerary
A Challenge Unlike Any Other
Unlike many CYTC attempts that begin in January, Jackrabbit’s strategic late-April start is designed to help him achieve something few others have managed: staying on each trail to completion without having to hop between trails to avoid seasonal challenges.
"A lot of people try to start in January, but what happens? They'll start on the AT, run into New England, and it's super frozen over in March. Then they've got to hop trails," Jackrabbit explains. His carefully timed approach gives him the best chance to navigate notoriously difficult sections like the Sierras, Colorado, and New Hampshire without weather complications forcing trail switches.
For Jackrabbit, this challenge represents more than just impressive mileage. It combines two of his greatest passions: the complete freedom of thruhiking with the structure of competitive racing. However, the only competitors he’s facing are himself—and the clock, of course.
"Thruhiking has always been this vacation period of absolute freedom—nowhere to be, nothing to do. If you want to take a zero, you take a zero. Racing is not that way. You need to be doing specific things or you'll fall behind," he says. "This is like a combination of those two things."
Behind his attempt lies a significant personal sacrifice. Jackrabbit left his highest-paying job ever, ended a meaningful relationship, and lived in a basement for six months to finance this adventure. When asked if he feels grief about these sacrifices, he admits: "A little bit, but the draw of getting out there is still bigger. I don't want to wait anymore years."
Mind Over Matter
Jackrabbit doesn't believe the physical demand of hiking 30+ mile days will be his greatest challenge. Instead, he worries about maintaining consistency over eight grueling months and the isolation that comes with moving at record pace.
I'llprobablybethefastestpersononeverytrailunlesssomeone'sgoingforsomethingelseIdon’tknowof.It'sgoingtobealotoflonelymilesandcampingbymyself.
This represents a significant departure from the typical thruhiking experience, where trail communities or "trail families" often become crucial support systems. The camaraderie of shared struggle has always given him strength on previous hikes, yet it’s something he’s willing to forgo for the glory of stepping over the finish line.
When confronting inevitable low moments, Jackrabbit admits that fear of public failure provides motivation—he's intentionally public about his goals to create "self-made pressure." Yet he recognizes this isn't enough.
Idon'twanttopinitonvalidation,butthereissomeelementtothat.Ineedmyreasonthisyeartobegreaterthanthat.IthinkI'mstillsearchingforwhatthatisrightnow.
For Jackrabbit, this journey isn't about superhuman abilities. He emphasizes that people who complete such feats aren't exceptional—"they're not Superman, they're not millionaires with all the muscles and time...it's the cashier at Walmart."
As his start date approaches, Jackrabbit remains focused on his core goals: completing the PCT, CDT, and AT by the end of 2025—and potentially setting a new speed record while making thruhiking history.
This story is one in a series following Jackrabbit’s 2025 CYTC attempt. Follow along his journey on the Build A Pack blog, where we’ll continue to update you on his progress. For more adventure stories like this, check out our Community Stories.
