Travel freely, spontaneously and indefinitely. These stories, interviews and discussions are tailor-made for hitchhikers, backpackers, couchsurfers and all who love to travel.
Starting his 20th year on the road, Kenny hitchhikes from Colorado to Wyoming, then takes a gamble through Nevada to Arizona.
Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com (https://www.triphopping.com/)
====
Support the show and Kenny's other projects while getting some bonuses here: https://www.patreon.com/kennyflannery (https://www.patreon.com/kennyflannery)
Kenny's written two books available on Amazon in paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm (https://amzn.to/2IynlFm)
"Nomadic Moonlight": https://amzn.to/40NjWc4 (https://amzn.to/40NjWc4)
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com (http://www.freestyletravelgear.com/)
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping (https://www.youtube.com/Hopping)
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com (http://www.hobolifestyle.com/)
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery (https://mailchi.mp/73c728259c7a/kennyflannery)
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend (https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend)
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8 (http://www.airbnb.com/c/kflannery16?s=8)
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931 (https://ripstopbytheroll.com/?rfsn=6483074.61c931)
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com (http://www.freestyletravelshow.com/).
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428 (https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428)
http://www.twitter.com/freetravelshow (http://www.twitter.com/freetravelshow)
http://www.facebook.com/freestyletravelshow (http://www.facebook.com/freestyletravelshow)
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss (https://anchor.fm/s/ddb5efa4/podcast/rss)
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
21 Jun 2026
#132 - Hitchhiking from North Carolina to Colorado
Kenny hitchhikes from North Carolina to Colorado via Indiana, Michigan, Minnesota, Iowa, and Kansas City. Catch up with friends, stealth camp, deal with police, drink some beers, and take the ride.
Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com (https://www.triphopping.com/)
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform (https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform)
====
Support the show and Kenny's other projects while getting some bonuses here: https://www.patreon.com/kennyflannery (https://www.patreon.com/kennyflannery)
Kenny's written two books available on Amazon in paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm (https://amzn.to/2IynlFm)
"Nomadic Moonlight": https://amzn.to/40NjWc4 (https://amzn.to/40NjWc4)
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com (http://www.freestyletravelgear.com/)
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping (https://www.youtube.com/Hopping)
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com (http://www.hobolifestyle.com/)
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery (https://mailchi.mp/73c728259c7a/kennyflannery)
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend (https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend)
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8 (http://www.airbnb.com/c/kflannery16?s=8)
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931 (https://ripstopbytheroll.com/?rfsn=6483074.61c931)
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com (http://www.freestyletravelshow.com/).
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428 (https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428)
http://www.twitter.com/freetravelshow (http://www.twitter.com/freetravelshow)
http://www.facebook.com/freestyletravelshow (http://www.facebook.com/freestyletravelshow)
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss (https://anchor.fm/s/ddb5efa4/podcast/rss)
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
7 May 2026
#131 - On The Road With Christian Cronin
Kenny talks to a friend and previous guest, Christian Cronin, as they cruise out of Mississippi on a little road trip. After, Kenny catches you up getting from Peru to Florida, a casino fail, doing bike deliveries, and hitchhiking to Mississippi to make his latest backpack.
Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com (https://www.triphopping.com/)
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform (https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform)
====
Support the show and Kenny's other projects while getting some bonuses here: https://www.patreon.com/kennyflannery (https://www.patreon.com/kennyflannery)
Kenny's written two books available on Amazon in paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm (https://amzn.to/2IynlFm)
"Nomadic Moonlight": https://amzn.to/40NjWc4 (https://amzn.to/40NjWc4)
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com (http://www.freestyletravelgear.com/)
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping (https://www.youtube.com/Hopping)
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com (http://www.hobolifestyle.com/)
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery (https://mailchi.mp/73c728259c7a/kennyflannery)
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend (https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend)
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8 (http://www.airbnb.com/c/kflannery16?s=8)
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931 (https://ripstopbytheroll.com/?rfsn=6483074.61c931)
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com (http://www.freestyletravelshow.com/).
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428 (https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428)
http://www.twitter.com/freetravelshow (http://www.twitter.com/freetravelshow)
http://www.facebook.com/freestyletravelshow (http://www.facebook.com/freestyletravelshow)
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss (https://anchor.fm/s/ddb5efa4/podcast/rss)
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
64,965
Score snapshot 15 Sept 2025
Apple Podcasts (US)
4.9 / 5
17 ratings
Spotify
5.0 / 5
5 ratings
Podcast Authority Score: 69 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
83
Social presence
0
YouTube
85
Engagement
51
Contact Freestyle Travel Show
Guest appearances
Books guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Host of Freestyle Travel Show?
Claim your podcast to manage its listing and keep your show details accurate.
Pod Engine is an independent podcast discovery and analytics service and is not affiliated with or endorsed by this podcast. Artwork and show content belong to their owners. Full legal notice.
Explore this show Podcast research with Pod Engine
