When I was younger I wanted to be a hobo. I loved Louis L’Amour’s Education of a Wandering Man and thought I could do something similar by traveling across the United States, working as I went. It never happened, but the thought never entirely left me either…So, here is an ode to something that has never been and likely never will be, but still captures my imagination.

Hobo Convention

The Hobo Convention is held annually in Britt, Iowa. The convention has been occurring for over a hundred years and draws many hobos together on an annual basis – though numbers have been dwindling with the passing of time.1Vice did a fascinating documentary video about the difficulties of being a modern hobo and attending the hobo convention.

Today’s Hobos

  • Nora Dunn has been traveling worldwide since 2006. She runs “The Professional Hobo” and shares how she has made traveling an integral part of her lifestyle and how others can do so too.
  • Chad and LeeAnn Lawie are “hobo sailors.” They began sailing (or at least Chad did) in 2003.
  • While your children might hate you, you could try being a hobo family like Lightnin’ Lauren O’Wayne and Crackerdog Sam (and their two little ones: Miko Lint Picker and Alrik Irontrousers the Land Pirate). Lauren blogs at hobomama.

Being a Hobo

  • There is a lot that goes into being a hobo and doing it at least semi-comfortably/safely. A good place to start is wikiHow’s aptly titled, “How to Become a Hobo” which is beautifully illustrated.
  • wikiHow has another useful article entitled “How to Ride Your Bike Across the Country.”
  • See the “Equipping to Be a Hobo” section at the end of this article for my theoretical choice of equipment if I were a hobo.
  • Not something you think of every day, but the question of relieving oneself – especially number two – is an important one. My always helpful sister (Anne) shared this fairly extensive article with me.


Equipping to Be a Hobo


  • Sleeping Bag – I’d plan on sleeping outside most nights, and traveling cross-country things could get a bit cold. I’d want something that can handle very low temperatures, is water resistant, has good durability, and is relatively small (remember, everything going with you has to fit on your back).2REI has some excellent articles on sleeping bags including “Sleeping Bags for Camping: How to Choose” and “Sleeping Bags for Backpacking: How to Choose.”
  • Tent – You could sleep out in the elements or build your own shelter at every stop, but I’d rather bring a compact, pliable, water proof tent.
  • Toilet Paper – Yes, I want some of the comforts of home. I figure one roll should be sufficient – can pick up additional rolls as necessary along the way.
  • Hand Sanitizer – I wouldn’t bring regular hand soap or shampoo, etc., expecting to be able to pick this up in towns as I went, but a small container of hand sanitizer would be helpful from the start.3I figure I would take showers at public pools, public universities, or if someone opened their house.
  • Plastic Bag (2x) – One for placing wet/dirty clothing in, the other to put around the sleeping bag to prevent it from getting damp when sleeping.4There may be some sort of “cover” for sleeping bags I am not aware of that would better fulfill this purpose…



  • Smartphone – Wait? You are going to bring a smartphone? Of course. It provides the ability to call for help in an emergency, help me get directions if I am lost, and so on.
  • Laptop – Yes. A hobo works – and I’ll be willing to work as a farm hand, painter, or any of a number of other trades…but it also makes sense to do some IT work on the road – building websites, fixing computers, etc. It will also allow me to blog my travels.7That said, my laptop will probably be quite small – selected for its size and weight rather than speed. I’d also consider using a bluetooth keyboard and mouse with my smartphone.


  • Bicycle – Technically, you don’t need a bicycle…in fact, I’ve been up in the air about it. The nice part of a bicycle is it makes travel more speedy (though not too speedy) and provides extra storage. The negatives are that it requires maintenance and will make taking a friendly car ride more difficult (or impossible).
    • Some electric bikes look especially interesting…I know, some might consider that cheating, but I don’t. If one could combine an electric bike and a collapsible bike, that would be the bomb.8Do I actually talk like that? Probably not.
    • If using a bicycle, you’d definitely want safety lights, the Blaze looks interesting (but too expensive).
    • It would also be great if I could find a way to harness the electricity being generated by the bicycle to recharge my electronics – especially the smartphone and laptop.
  • Cover – I’ll need some sort of cover for the bicycle for when the elements are nasty (rain, snow) to keep it in good operating condition.
  • Lock – Unfortunately, I’ll also need to take a lock of some sort along.
  • Spare Parts  – An extra set of bike tubes (2x), maybe an extra chain (1x), extra set of brakes (1x).


  • Water FilterLifeStraw Personal Water Filter ($20).
  • Clif Bars – These hold up over time, don’t need to be refrigerated, provide decent nutrition and energy, and are fairly reasonably priced.
  • Soylent – A powder that only requires water and has a long shelf life before mixed, provides complete basic nutrition.


  • Small Shovel/Hoe – Probably military issue. Will be useful for numerous tasks – such as digging holes for bodily waste or making fire pits.
  • Baseball Bat – For use as a defensive measure.9Can’t take a pistol across state borders without a permit for each state; imagine there are various laws about large knives…still need to look into it, but I’m guessing *most* places it is legal to carry a baseball bat (I think I’d affix it to the bicycle). Both human and animal issues could arise.

Places To Go, People To See

If I was hobo’ing, here are some of the sights I’d consider taking in along the journey.

(Bolded indicated I’d almost definitely go to these locations, regular font equals, I would if it fits into travel plans).

See the separate international page for information on countries I’d like to visit.


I’d be interested in hearing about opportunities.

  • Especially in short-term, volunteer work with various non-profit organizations/churches.
  • I work in Information Technology on everything from workstations to servers to storage arrays to web-based site/application development.
  • I enjoy cleaning and organizing and brainstorming and I’ve done a good variety of manual labor – from being a farmhand to field stone masonry.


  • Burning Man – Nevada – Something weird.
  • National Hobo Convention – Britt, Iowa – B/c how could one be a hobo w/out attending the hobo convention?
  • Cirque du Soleil – Nevada – Probably wait till I reached Las Vegas to go to one.
  • CiviDay – These occur throughout the world, they are group endeavors to move forward the excellent open source CiviCRM project – I’d love to drop in and be part of one.
  • SXSW Interactive – Austin, Texas.
  • TED Conference – Monterey, California.
  • Pop!Tech – Camden, Maine.


  • St. Vincent Archabbey – Latrobe, Pennsylvania – The oldest Benedictine monastery in the US, also one of only two archabbeys in the US.
  • The Community of Jesus – Orleans, Massachusetts.
  • Portsmouth Abbey – Portsmouth, Rhode Island.
  • Weston Priory – Weston, Vermont – Known for their contributions to contemporary Catholic songs.
  • St. Anselm Abbey – Goffstown, New Hampshire – Also has an associated college.
  • St. Leo Abbey – St. Leo, Florida.
  • St. Joseph Abbey – St. Benedict, Louisiana – Also home to a seminary.
  • St. Louis Abbey – Missouri.
  • Conception Abbey – Missouri – Has an associated seminary.
  • Subiaco Abbey – Arkansas.
  • Monastery of Christ in the Desert – Sante Fe, New Mexico – Built by George Nakashima.
  • St. Meinrad Archabbey – Indiana – One of only nine archabbeys worldwide, one of only two in the US. Also home to a seminary and the Abbey Press.
  • St. Gregory’s Abbey – Shawnee, Oklahoma.
  • St. Gregory’s Abbey – Three Rivers, Michigan – An Episcopalian male community following the rules of St. Benedict.
  • St. John’s Abbey – Collegeville, Minnesota – Second largest Benedictine monastery in Western Hemisphere.
  • Christ the King Abbey – Schuyler, Nebraska.
  • Assumption Abbey – Richardton, North Dakota.
  • Abbey of Our Lady of the Holy Trinity – Huntsville, Utah.
  • Mt. Angel Abbey – Mt. Angel, Oregon – Has an associated seminary and museum.
  • Silicon Valley – Southern San Francisco Bay Area, California – The heartland of technology innovation.
  • Intentional Communities – I’d like to stop at a number of intentional communities – secular and religious.
  • Couch Surfing – I’d like to do a good bit of couch surfing as well, and while this may not be a “community” in the sense that individuals are together at a geographical location, it is a “community” in the sense of common shared culture/values (the practice of opening one’s home to strangers, etc.).
  • RV Parks and Campgrounds – These sort of areas also form their own sort of communities. I mean the ones where there are “long-timers” who live there over the summer, returning each year, perhaps a few who stay year-long, and so on.


  • Woodland Hills Church – St. Paul, Minnesota – Greg Boyd is the pastor here. Boyd is a controversial evangelical figure who advocates open theism, holds unpopular political views, believes in annihilationism, and contributes to the controversial BioLogos Foundation which discusses the intersection of Christianity and science.10His book Letters to a Skeptic, which I read as a young teenager, was influential in encouraging my faith.
  • Bethlehem Baptist Church – Minneapolis, Minnesota – John Piper was long the pastor here. His work Desiring God was influential in my spiritual development. If I could meet with Piper, I’d make an extra effort to get here.

Educational Institutions

  • Massachusetts Institute of Technology – Hugely influential center for technology/sciences – where to even begin with their alumni’s influence on the world? – Maybe this Wikipedia article.
  • Harvard University – Cambridge, Massachusetts.
  • Yale University – New Haven, Connecticut.
  • Johns Hopkins University – Baltimore, Maryland.
  • Washington and Lee University – Virginia – Robert E. Lee was president here.
  • University of Virginia – Virginia – I hosted an online interview with Patricia Click, author of Time Full of Trial, back in the day (err, right before or after the dot com crash) and I’d love to meet her in person.
  • Baylor University – Waco, Texas – They are a Christian educational institution and have an accredited medical school.
  • Cedarville University – Ohio – I almost went there for my undergraduate education.
  • Oberlin College – Ohio – Charles Finney was president here.
  • University of Notre Dame – Notre Dame, Indiana.
  • Wheaton College – Wheaton, Illinois – I wanted to go here as an undergraduate, it was my first pick. I received an acceptance letter…11but was informed I was on the waiting list. It seemed like every few days I received a postcard informing me x number of students had dropped out so x number on the waiting list could enter – but the entire time I was on the waiting list only women dropped out…not a single man… One of the premier Christian institutions of higher education.
    • Home to the Marion E. Wade Center, “a major research collection of materials by and about seven British authors…” which include G.K. Chesterton, C.S. Lewis, Dorothy L. Sayers, J.R.R. Tolkien, and (most important to me) George MacDonald.
    • Rolland Hein, an expert on all things MacDonald, was also a professor there and is now Professor Emeritus of English, maybe I could arrange a chat.
    • There are numerous other luminous minds there like Andrew Hill, Daniel Block, Douglas Moo, Leland Ryken, and John Walton.  Of course, I’d also want to visit the Archaeology Museum.
  • Calvin College – Michigan – I love the CCEL and would love to meet Harry Plantinga in person.
  • Colorado Christian University – Lakewood, Colorado – Formerly home to Dr. Larry Crabb, a leading Christian psychologist.
  • Brigham Young University – Utah – Because I’m fascinated by Mormonism.
  • Fuller Theological Seminary – Pasadena, California – One of the most widely respected Christian seminaries – but also a bit controversial as some of its faculty have strayed outside the realm of what many evangelicals consider core orthodox beliefs. I’d love to meet David Augsburger (counseling), John Goldingay (OT), Archibald D. Hart (psychology), J.R. Daniel Kirk (NT, whom I currently know only digitally), Richard J. Mouw (formerly President of the Seminary), Kara E. Powell (a lead innovator in youth ministry).
  • Biola University – La Mirada, California – Another of the premier higher education institutions within Christianity.
    • I’d love to meet Clinton E. Arnold (Powers of Darkness), William Lane Craig (one of the foremost Christian philosophers of our day), John H. Coe (spiritual formation), J.P. Moreland (prolific author for IVP, philosopher), and Bruce S. Narramore (one of the early and core Christian counselors).
    • They are at the leading edge when it comes to innovative education, imho, with endeavors like Open Biola…and I suppose it would make sense to swing by the Art Gallery if I’m there.
  • University of California (Davis) – Davis, California.
  • University of California (Los Angeles) – Los Angeles, California.
  • University of California (Berkeley) – Berkeley, California.
  • Stanford University – Stanford, California.
  • Singularity University – NASA Research Park, Moffett Field, California.
  • I’d also consider swinging by Liberty12Founded by Jerry Falwell, one of the largest Christian universities. (VA), ORU13Mark Rutland served as president. (OK), George Fox University14Richard Foster’s alma mater. (OR), and/or Master’s College and Seminary15John MacArthur founded. (CA) if they happened to be nearby.


  • Nashville, Tennessee – Not on the top of my list – but from a contemporary music perspective could be interesting.
  • Asheville, North Carolina.
  • Orlando, Florida.
  • Portland, Oregon.
  • Denver, Colorado – No, not b/c it has legal marijuana.
  • Boulder, Colorado – College town.
  • Colorado Springs, Colorado – A hot spot for evangelicals – headquarters for organizations like Christian and Missionary Alliance, Compassion International, David C. Cook, Focus on the Family, The Navigators, and Young Life are all there.
  • San Diego, California.
  • Seattle, Washington.
  • New Orleans, Louisiana.


I’ve begun moving places to go onto a separate places to go page here.


I suppose if I’m going to be going through a number of states, I should plan on doing some skiing – though unfortunately that means that I’d have to travel to the state during the winter – which will likely be rather cold.

  • Jackson Hole Mountain Resort – Jackson Hole, Wyoming.
  • Alta or Snowbird Resort – Alta/Snowbird, Utah.
  • Telluride – Telluride, Colorado.
  • Vail – Vail, Colorado.
  • Park City/Deer Valley/The Canyons – Utah.
  • Snowbird – Snowbird, Utah.
  • Squaw Valley, California.
  • Mammoth Mountain, California.


  • Grand Canyon – If I’m in Las Vegas, I might as well.
  • Ashfall Fossil Beds State Historical Park – Royal Nebraska – Bill Nye mentioned it in his debate with Ken Ham, looks pretty amazing – fossils preserved by ash still in their original locations.


  • Eugene Peterson – Montana – Peterson is one of those Pastors I look to for guidance – not in person, but through his books and articles. I’d love to meet him in person, if he’d be willing to meet for an hour or two with this traveler.
  • Frederick Buechner – Vermont – I’m not sure if Buechner is still in Vermont, but wherever he is, I’d like to visit him. His book Sermons in the Dark served as balm to my soul as I struggled with my own faith.
  • Malcolm Boyd – Los Angeles, California – Malcolm Boyd wrote the excellent book of prayers, Are You Running with Me, Jesus? He was an activist during the civil rights movement, but is best known now for his embrace of the homosexual lifestyle. I’d like to hear about his struggle to come to this decision.
  • Kenneth Boa – Atlanta, Georgia – Boa’s books are amazing in their depth and scope. I am reading Conformed to His Image now, I was fascinated by his doctoral thesis, and so on. I’d love the opportunity to chat with him.
  • Mark Rutland – His book Streams of Mercy has been one of the most influential books in my life.
  • Larry Crabb – Silverthorne, Colorado.
  • Henry Cloud – Irvine, California.
  • John Townsend – Irvine, California.
  • Gary R. Collins – Libertyville, Illinois.
  • David Allen.
  • Daniel Amen.
  • John Eldredge.
  • Max Lucado.
  • Rick Warren.
  • Neil T. Anderson.
  • Richard Foster.
  • Richard Swenson.
  • Joseph Girzone.
  • Mark Noll.

Some Help From Quora

These are questions I have posted on Quora related to being a hobo that have provided insightful answers.

Related Terms

  • Loosely Related (Neutral/Positive): hitchhiker, couchsurfer, frugal traveler, vagabond, drifter, backpacker, trekking, nomad, digital nomad, peripatetic, king (or queen) of the road, rambler, rolling stone, wanderer, hippies, journeyman, adventurer, bohemianism, romani, gypsy.
  • Incorrectly Associated (Negative): vagrant, tramp, bum.