Today on the Free Outside Podcast, I talk with Connor “Jackrabbit” Chapdelaine, who’s attempting the Calendar Year Triple Crown—thru-hiking the Appalachian Trail, Pacific Crest Trail, and Continental Divide Trail all in a single year. We break down how the idea got planted during a hike on the AT, what it takes to train for 8,000 miles, and why he’s bringing a pillow, a stove, and maybe even a thermos.

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Connor shares his strategy for navigating snow in the Sierra, reroutes on the PCT, and fires on the CDT—plus his plan to survive town stops without spending his entire budget. We also get into ultralight gear hacks, and his favorite trail meals. Connor breaks down his food tier list (spoiler: mushroom Knorr = trail exile) and how his dad is helping run the back-end logistics with a label maker and full “dad command center.”

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If you’ve ever been curious about the logistics, gear, food, and mindset needed to thru-hike the PCT, CDT, and AT in one year, this episode is packed with real insight and ridiculous stories—including tuna and peanut butter wraps, dry-scooped coffee, and a thru-hiker potluck that no one asked for.

Chapters

04:00 The Aspiration of the Calendar Year Triple Crown

10:30 Overcoming Obstacles in the Journey

13:51 Planning and Timing for Success

19:25 Budgeting for the Adventure

24:20 Family Support and Logistics

25:12 Training for High Mileage

31:29 Food Choices on the Trail

37:58 The Quirks of Trail Humor

38:51 Trail Food Favorites and Disasters

40:56 Resupply Strategies and Bargain Finds

41:59 The Art of Coffee on the Trail

43:46 The Triple Crown Experience

45:38 Friendships Formed on the Trail

47:59 The Emotional Connection to Hiking

50:04 Gear Essentials for Long Trails

56:14 The Importance of Comfort Items

59:34 Post-Hike Plans and Future Goals

01:05:15 Memorable Trail Names and Their Stories

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