What if sticking out your thumb on the side of the road turned into one of the most life-changing experiences of your journey? After completing the Great Divide Trail, Jada set out to hitchhike 500 miles back to Montana—and along the way, she discovered the power of trust, the kindness of strangers, and the unexpected magic that happens when you leave room for it. In this continuation of her story, Jada shares unforgettable encounters with trail angels, surprising meals with strangers, and the lessons that only long-distance hiking can teach. From trail magic to her mantra of “live so hard, it hurts,” Part 2 of our conversation will inspire you to lean into life, embrace the unknown, and seek out your own adventure.

Resources:

• Follow Jada on Instagram: @whereisjadaa
• FarOut Guides
• Read Wild by Cheryl Strayed
• Please follow the show, leave a 5-star review if you love it, and share with your travel buddies
• Don’t miss Jackie’s behind-the-scenes communications - hop on our email list at TravelingJackie.com

Massive thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!

Produced by NOVA

What if the accident that nearly ended you became the spark that set your life on fire? A snowboarding crash left Jada “Flo” bedridden—until she turned recovery into an 800-mile trek across Arizona that launched her into the world of long-distance trails. In this episode, we trace her journey from deserts to the Canadian Rockies and the lessons she’s learned about resilience, simplicity, and giving yourself permission to pivot. Part two (Ep. 194) continues with trail angels, hitchhiking, and the kindness of strangers.

Resources:

• Follow Jada on Instagram: @whereisjadaa
• FarOut Guides
• Read Wild by Cheryl Strayed
• Please follow the show, leave a 5-star review if you love it, and share with your travel buddies
• Don’t miss Jackie’s behind-the-scenes communications - hop on our email list at TravelingJackie.com

Massive thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!

Produced by NOVA

What if the biggest party on two wheels was happening in the middle of Iowa every summer—and you were invited? Cyclist Eric Whalen joins Jackie to share the magic of RAGBRAI, the week-long ride across the state that’s equal parts endurance, community, and carnival. From pies and slip-n-slides to costumes and late-night music, Eric reveals how this ride became a father-son tradition and why it’s one of the most joyful cycling adventures in the country.

Resources:

• Learn more about RAGBRAI: Register’s Annual Great Bicycle Ride Across Iowa
• Check out Pork Belly Ventures for charter services and added comfort on the ride
• Join the conversation on the RAGBRAI Subreddit
• Follow Eric on Instagram: @whaylen
• Please follow the show, leave a 5-star review if you love it, and share with your travel buddies
• Don’t miss Jackie’s behind-the-scenes communications - hop on our email list at TravelingJackie.com
• Be part of the conversation! Watch the video version by subscribing to our YouTube channel today
• Massive thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!

Produced by NOVA