About Kenny

Hey everyone! I'm Kenny Flannery, I started traveling in 2007, I've been living out of my backpack ever since, hitchhiking around the US and the rest of the world. I started HoboLifestyle.com to share my stories and advice, then later started the Freestyle Travel Show, a free podcast for people who want to listen to stories and advice as I'm on the go.

PayPal: HoboLifestyle@gmail.com (for those wishing to leave a tip or encourage my travels).
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Meet Kenny: This is a form for anyone who'd like to host me if I come through their town, grab a beer, offer a ride or anything like that.

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Questions I'm asked regularly

Where are you from?

I grew up bouncing between Connecticut and New York, mostly Connecticut. There were a couple stints of Utah and Maine thrown in there. After high school I moved near Orlando to go to an audio school, then back up to New York City, then eventually got bored with being stationary and started traveling.

How long have you been traveling?

Since the summer of 2007.

This whole time?

Yes. The longest I've been in one place in this time is just over a month.

How do you afford to travel?

It doesn't cost much, in fact it's more expensive to stay in one place, rent and whatnot.

OK, but how do you make money, do you have it saved up?

I don't make a lot of money, some odd jobs here and there.

Then how do you support yourself?

My lifestyle doesn't require much cash. I eat cheaply and travel freely, meet generous people and never turn down a good meal or a beer. Student loans can throw me a curve ball sometimes, but I work them out one way or another. Once I had $20 in Vegas and a video roulette machine turned it into $240, barely enough, but that paid the loan that month. Other times odd jobs have presented themselves, anything from an hour digging a hole to a few weeks helping with harvest.

You can read my post Spending and Making Money During Extended Travel to dig into that some more.

How do you afford to get around?

Most of the time I hitchhike.

Isn't hitchhiking dangerous?

There's a better chance of getting into a car accident then getting picked up by a serial killer or some such, hitchhiking's good times.

Do any weirdos pick you up?

That's what I look forward to, but they're only weirdos until you get to know them. Most of the time, though, the people picking me up are just generous good spirited people. Some used to hitchhike "back in the day", others have never picked up a hitchhiker before and wanted to give it a shot. Some are just looking for someone to talk to on a long drive, some people go out of there way to help a hitchhiker get to a better spot.

I write a lot about hitchhiking, but you check out my hitchhiking page to get started on tips, info and links to stories and videos.

Where do you sleep?

Wherever seems to be the place to be. Sometimes camping, sometimes with friends or family, new friends or I use couchsurfing. I also wrote a post called Where to Sleep While Traveling.

What's couchsurfing?

CouchSurfing.com, it's a website that let's you find locals who will let you crash on their couch or spare bedroom for a night or three. It's all free, you meet someone awesome most of the time and there's millions of people doing it across the globe. There's also new sites like TrustRoots.org that function in a similar way.

I have a whole episode about hospitality networks on my podcast you can listen to.

Isn't that scary, strangers and stuff?

No. It's awesome. It's safe. Have a good time!

What do you carry?

Clothes, a sleeping bag, some camping stuff... I wrote an insanely detailed post about this if you're really interested, Ultralight Packing Guide for Freestyle Travel.

What's your favorite place?

Depends on my mood, time of year, who I'm with, bla bla and yes. Flagstaff is a great town, Zion (southern Utah) is incredible to see, Chico is a cool community, New York City is always a happening place with good friends, Philadelphia has great food and bars, Las Vegas is a clusterfuck of insanity, Alaska is wide open, Vancouver has a lot of flavor and options, Savannah let's you drink on the streets, Jackson Hole is raw beauty, Belgium's got tasty beer, so does a lot of the USA these days, New Zealand is a traveler's paradise and there's plenty of other great places.

Are you hungry?


You want a beer?

Of course, thanks!

When are you gonna stop traveling?

I haven't thought that far ahead.

Those are the typical questions I'm asked. I love this lifestyle. The travel, the hitchhiking, the empty calendar that can be filled with endless anythings - it's all good. It's not about any one of those aspects entirely, it's about going with what's going, just loving it all. I meet people all the time with the spirit, more and more, some travel heaps, some not at all. They all got it. Life is good.

Tip jar, choose your generosity:
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  1. What happened to all the old stories ? Really interesting stuff and you have that writing style that makes the reader feel like they are there. Stay safe and keep living life to the fullest.

  2. I'll prefix this by saying interesting life choice.
    But certainly not a hobos life. Hobos rode
    rails and didn't take buses , hitchhike or stay
    in hotels. To that you do a discredit to poor
    people who's only method to travel was rails.
    I'd suggest that a more appropriate title would
    be travelerlifestyle.
    I've watched roughly 25 or so of your videos
    and find them convoluted as far as the order
    they appear. And length for a trip from LA to
    NYC in a ten to fifteen minute video seems
    way to short. I would also suggest that on
    trips you make part 1,part 2 etc. Not I was in
    Miami and now NYC. Theirs no depth in the
    story. Plus, what about weirdos, homosexual
    offers for money, loose women, drunks, really
    drunk drivers, crimminals on the lam, drug
    addicts,dangerous people. All who pick up
    hitchhikers. I know these people are picking
    you up as well. You act like its a carefree life,
    but we both know it isn't. And what about
    them guilable 20 somethings who see your
    videos and think its all fun and games, but
    because they see your videos , end up in the
    wrong car and killed or tortured then killed.
    Like your going off with a stranger who just
    gave you a ride to sleep at his house. The
    knife you carry won't win in a gun fight!
    What about hours under a wet bridge for a
    day or more with no rides , no food or water?
    Or that kid that stuck in El Paso heading out
    to Houston with 745 miles of desert between
    them, stuck for days and unlike you doesn't
    have parents to pay for a bus? For a hobo you
    ride a train & bus and sometimes planes a lot!
    Dude your not a hobo.
    You claim you do odd jobs, lets see that! I
    suspect your parents are subsidising you , thus
    you broke one minute and have money the
    next , plus all your many city bus, bus, train
    and plane travel. As well numerous hotels you
    stay in.
    You may not know it, but in a way your
    responsible for people who think traveling by
    thumb is a breeze and get hurt, killed or are
    distressed by experience. You should do a
    video on dangers & hardships of hiking.
    Now I dont down you on monetizing hiking
    or website , videos are entertainment, and
    has a intrinsic value. Plus it offers more videos.
    The market will see if demand means

    How do I know of all this -
    I hitched from 1975 to 1986 - 1995 to 1997.
    I was a little 18 year old dude from Florida
    when I started .
    The only bus or plane I took was given to me
    by a old man from WI , who gave me a ride one
    rainy night from Rockford Il to Lincoln, NE.
    then flew me on comuter plane to Denver, Co
    Plus a bus ride by family from Aurora, CO to
    Fl. Different trips in greater Denver.
    Yes, theirs so mighty good people out there, but
    also many people who would hurt you or me in
    a second and really feel nothing about it.
    Dangerous people.
    I hope you took this in the spirit it was intended
    as! Helpfull advice.
    One final suggestion, I would look up
    stobethehobo on youtube and look at the way he
    edits and length of shot "cinematography " and
    music to videos. Sorry, but much better layed
    out then yours. He actually played classic rock
    on piano for videos. Sadly Jim " stobe the hobo "
    die in a freight train accident riding the rails
    outside Baltimore, Md.
    Nov 8th 2017.
    R.I.P Stobe
    You should try Madison WI, home of University
    of Wisconson. College town, state street is main
    drag! Very layed back, cops are waaaaay cool.
    If you want to comment back email is -

    Good luck and have fun, lifes to short not
    to , but utmost, be safe out there man!

    1. Heyo! Didn't see this comment until now. Not really worried about the semantics with the word "hobo", the site is what it is and I am whoever I am, named the site over ten years ago. You're right on with the videos, that's why I stopped doing them for the most part. Shooting them and even editing them was interrupting the good times themselves. They would have been better if I filmed the people who gave me rides as well, but that rarely seemed like a good move in the moment. For all the stories you're looking for (drunks, wet nights, long walks, getting hit on, murder admissions, coyotes, meth head truckers, etc) you'd have to read through the actual blog posts, it's all in there, as are the descriptions of various odd jobs and money grabs (bottling beer, cali pot harvest, contests, projects etc). Better yet there's the podcast (Freestyle Travel Show) which has all my up to date stories whereas the blog has a three year lag at the moment. Lastly the weed stashing (not sure which story your referencing but I'm sure there's many) I'm just not a big smoker, so usually for a rainy day or a friend. Shoot me an email if you want, could always do a podcast episode as it sounds like you've got some stories yourself. Cheers.

    And dude whats with you getting a joint and then
    saying you stashed it for another day? For what
    months, years later? Or that for your parents sake
    you said that?
    Here's a hint from a old school pot smoker & hitch
    ( your waistband )
    On the "inside" top seem where the button for jeans
    or shorts are, cut a small 1/4 to 1/2 inch slit . It
    should be hollow. If joint ,wrap in thin card
    board and then plastic. Both can be found roadside,
    If loose weed, bundle in soft plastic and stuff in
    slit. For bigger amounts bindle into grams and
    repeat slit on both left and right side.
    Did that and was stopped mamy times and never


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