Summary: In 2018 I quit my job, and walked 1500 miles from the Atlantic Ocean on the coast of Delaware, home to Iowa. I roughly followed a trail called the American Discovery Trail which goes coast to coast. In the spring I will be continuing from where I left off to walk to San Francisco. In the meantime I am creating artwork based on my experiences. I was in a creative slump as an artist, and so the adventure began. Ask me anything!


More proof to show I am the same hobo:

Comments: 957 • Responses: 57  • Date: 

TomIsNotATurtle740 karma

Do your feet hurt?

TheTrailArtist959 karma

Haha, they did. I’ve been off trail since October so they’re fine now, but my feet definitely took a beating. Blisters are one thing, and your feet tend to swell with that much use. As a result I went through 4 pairs of shoes.

flyingsaucerinvasion232 karma

Do you mean each pair bigger than the last?

TheTrailArtist401 karma

For the most part. My first pair was a set of trail runners I walked to from Lewes DE to Washington DC, by then I already needed a half size larger and switched. When I made it halfway through WV, they were too tight so I switched again to extra wide shoes. And my soles were wearing through into Iowa so I switched to another pair the same size.

temporarycreature24 karma

Why not a good pair of rucking boots? I highly recommend Go Ruck's new boots. I can sprint in them. They're fantastic and made for long distance walking with weight on your back (this is what rucking is). Boots, in general, are better for walking in because of the ankle support they provide.

TheTrailArtist37 karma

I will look into that. Shoes did okay for me, I wanted something that would dry quickly, but yeah I’m thinking of switching to boots for those Colorado mountains.

nessager699 karma

What item did you forget to bring?

TheTrailArtist901 karma

Hahaha sunscreen. Big mistake the first few days..

deepmonstertrance636 karma

Do you ever get songs stuck in your head and sing them to yourself for days at a time? What songs?

TheTrailArtist1527 karma

But I would walk 500 miles.. and I would walk 500 more just to be the man who DA DA DA DA DA DA DA DA DA

PoopsicleMan431 karma

Did you do any kind of prepping for this (ex: taking long walks, exercising at the gym, etc) or did you just get up and start doing it one day ala Forrest Gump? .

Bonus Question: How much weight have you lost?

TheTrailArtist433 karma

Honestly not as much prep as you might expect. I was working at a window factory which was very physically demanding, moving heavy things and being on my feet 50+ hours a week. I think that for sure helped build my stamina. And I would do long walks when I could on my days off. The biggest thing is slowly building up your miles when you first start your hike.

And surprisingly my weight stayed about the same give or take 10lbs depending on my last fill up on chicken nuggets.

LordSpud74295 karma

Have you ever thought about leaving small pieces of art behind for people to find, and documenting hints about it or posting it on social media, kinda like a scavenger hunt? I feel like a lot of people would jump on and follow this, I know I would be excited to see if you came anywhere locally

TheTrailArtist302 karma

That’s a really cool idea actually. Thank you. I’ll brainstorm some logistics about that

Gimmegimmegunshots290 karma

How many times have you been approached by police officers?

TheTrailArtist959 karma

About half a dozen. I expected more to be honest! The were mostly nice. For a section of my hike I pushed a baby stroller to carry more food and water and I had an officer respond to a cal because “a man is pushing a baby on the highway!!!” On another instance, there was nowhere to stealth camp in a small town so I flagged down a cop and was straight with him that I just needed a place to set up my tent. The cop was surprised but let me sleep in a park and even gave me his business card Incase other cops hassled me up the road.

Dmak641236 karma

My Grandfather used to travel like this. I highly doubt you can still do this, but he would sometimes ask to sleep in the county jail house overnight. And when he couldn't do that, he would camp in the cemetery. He told me the grass was much softer there.

TheTrailArtist91 karma

Haha might be a social experiment for me to try with the jail house.. and I have set up my tent at the edge of some cemeteries, they are usually good hiding places.

KaBar2272 karma

Do you meet other tramps on your journey? Because IMHO, you get major hobo points, and I think you need to hike yourself out to the National Hobo Convention in Britt, Iowa this coming summer.

Second weekend in August, every year, at Britt, Iowa. People start arriving about a week or so early. (Don't try to ride a train in--the bulls are all over Mason City yards and the Britt siding during the Convention. You'd just wind up in jail and miss the Convention.) Free camping, lots of activities, a small-town carnival celebration, a parade, hobo memorial service out at the National Hobo Cemetery, "election" of new King and Queen of Hobos, etc. The current king, Dutchman, has been riding trains for over fifty years. The current queen, Crash, is the daughter of former hobo queen, Half Track, and the step-daughter of "Preacher Steve" Stewart, who rode for over twenty-five years. You'd fit right in, bro.

TheTrailArtist106 karma

Haha I’ve heard of this convention but I’ve never been. I’d love to go, but I’ll probably be on the road by then so it will have to be another year. And yeah I meet all kinds of characters, I love hearing stories from other travelers. I’ve met a couple people that ride the rails, and some retired travelers love to reminisce about their hitchhiking days with me.

cacatua242248 karma

How do you pay for food, where do you sleep?

TheTrailArtist637 karma

I am pretty frugal with this walk. I saved up a good sum that I won’t starve, but I mostly eat dry food like trail mix, salami, and ramen noodles soaked in cold water. I also pig out at a fast food place once in a while. I sleep in my tent almost every night, which means “stealth camping” when I’m not in the woods. This often means hiding my tent behind a church, playground, or soccer field. On occasion complete strangers invited me to camp in their yard or even in their house, which adds an amazing layer to the trip. I stayed in an abandoned house once that was falling apart, and also squatted in a shed at a ski resort. I only stayed in a motel room once so far, because all my clothes were soaked and I needed a dry place.

14thismustbetheplace196 karma

What’s your plan on getting through the desert? That place changed me. It’s a kind of beautiful I had never experienced before.

TheTrailArtist237 karma

I plan to use a jogging stroller of some sort to carry more water. That’s my biggest concern. I did use a baby stroller to push more supplies for a part of my walk, and it has its pros and cons but yeah definitely need to carry a lot of water.

RAWR_time177 karma

What has been your scariest/most dangerous encounter thus far?

TheTrailArtist332 karma

Thunderstorms are something to be taken very seriously. Especially after I met someone that had survived a lightning strike and warned me to watch the clouds. A copperhead snake also fell out of a tree in front of me... and aggressive country dogs are not to be trifled with.

FuChunjian153 karma

What possessions do you travel with?

TheTrailArtist266 karma

The 3 main basics are of course tent, backpack, and sleeping bag. Besides that lots of little things like knife, a small first aid kit, journal, GoPro for documenting, trekking poles, water filter.. I don’t have an exact list because it tends to bounce around. My gear list is always changing.

mehtotheworld132 karma

how many miles do you average a day?

TheTrailArtist225 karma

When I first started it was 10-15, then 15-20, then 20-25 on really good days. I’m not sure of my exact average because I took a fair amount of “zero” days in between when I would walk to spend time with distant relatives or friends, and hang around a few days.

Superbeanietoon112 karma

Are you happy with your decision to leave your job and do this? What has been the most rewarding part? What do you think you’ll do once you finish?

Thanks for the AMA!

TheTrailArtist203 karma

I’m absolutely happy I quit. I was at a window factory which was decent pay, but long hours and very intensive labor. As I result I was totally sapped of creative energy when I would get home each day. The most rewarding part to me is feeling in control of my own life. It took me a long time to even convince myself to take the plunge, I feel more certain of myself and my decisions, I’m more goal oriented, and happier overall. Once I finish I definitely want to pursue more creative outlets. I’ve started a book and documentary which I don’t expect to make me rich, but it’s sparking my passions back up which I’m very thankful for.


What's the most beautiful thing you've seen on your journey?

TheTrailArtist398 karma

My girlfriend when I finally made it home.

rrwins124 karma

What???? I mean hwhatt!! I assumed you were single and needed this time to clear your head and find your soul mate and you had a gf this whole time?! How did she take it when you told her about your plans! You blew my mind bud. I'm in awe of what you do and thank you for doing this Ama. Wish you the best. Very fking cool.

TheTrailArtist179 karma

Hi again. I know some people probably think I’m selfish, and I don’t blame them. I actually warned her I was planning it before we even started dating. It was not an easy decision though. She has been my greatest source of strength throughout this. And though I’m doing this walk for personal reasons, I want to become the best version of myself I can for her. It was a great motivator to know every step I took was closer to her, but it’s gonna be very painful to leave again. She is my anchor though and I promised I won’t do any extensive traveling for a while after my walk.

lowtoiletsitter100 karma


Since it hasn’t been said, I guess I’ll be the asshole that asks because I know someone will:

How much money did you have before you started saving? Not many people can afford to quit a job because they feel like it and travel across the country without some sort of financial and/or social security system.

Now that’s out of the way...what I think what you’re doing is amazing! I’m glad you had the idea of just going with what you felt would make you happy and inspired. Safe travels!

TheTrailArtist130 karma

A lot of people want to know about money which I think is a fair question- for some backstory I graduated college in 2016 with a buttload of student debt. But there were no jobs with my majors (art and psych) hiring in my small town, so window factory it was. Through a lot of overtime, taking a side job at Walmart, selling a lot of my possessions I managed to pay ahead my on my student loans to keep the jackals at bay and save up.

It took a lot of hard work to save up to do this, and I funded myself. I know I am in a more privileged position than others as I have less responsibilities, no kids, no car payments, no house payment, ect. But I want others to know it is absolutely possible to make things like this happen, though obstacles are different for each person. The obstacles to start my walk were in some ways harder than the walk itself. I left for my walk with a little over 6k in my bank, which is more than enough as I don’t sleep in hotels and my main expense is just food.

famousforbeingfamous96 karma

Which state was the most surprising/different from your expectations?

TheTrailArtist290 karma

I’ll be real here- West Virginia. I try not to be prejudice but I did have some conceptions that I’d be seeing hillbillies making moonshine in their pickup trucks. But the people there were so good to me. I had strangers invite me to stay in their homes. I met so many amazing people. Not to mention the landscape was stunning.

itslenny95 karma

Awesome! I quit my job and did the Pacific Crest Trail 2 years ago, but the American Discovery Trail was what sparked my dream of doing a cross country hike in the first place. I chose the PCT because it's much shorter and a much more well established trail with less boring bits.

So, question... How do you cope with the long expanses of the midwest? Also, are you hitching much or trying to stick to purely walking?

(No hate for the midwest. I'm from Chicago, and love the midwest, but I also spent 2 years road tripping and it gets old even in a car)

TheTrailArtist78 karma

Awesome! The pct is definitely on my bucket list. That’s a fair question. One thing that helps is that I’m originally from the midwest, so I have some friends and relatives scattered across those states which I’ve been able to coordinate to walk to. It adds a cool layer to the adventure to catch up with people I haven’t seen in a long time.

Also I am hiking every step, not of the ADT per say but the goal is to hike every step from ocean to ocean.

Nebraska might not be the most exciting but it’ll be a good warmup for sweet sweet Colorado once I set off again.

Frawitz62 karma

How many buildings have you peed on?

TheTrailArtist126 karma

Nice try FBI. Haha really though; I had to “stealth pee” A LOT. I tried to be as respectful as I could though and not mark my territory on too many buildings..

3fjn3t60 karma

Which direction are you planning to turn in Albuquerque?

TheTrailArtist34 karma

Honestly I have not totally mapped out my route westward. I tend to wing it for the most part, as long as I know a water source is available. But when I near the desert that’s gonna be a lot more important.

CraazyGamerz55 karma

So, uhm where do you charge your phone and who's wifi you stealing?

TheTrailArtist65 karma

I keep a power bank and top off the charge every time I eat at a fast food place haha. And Starbucks, libraries mostly.

ghostofdevinbrown54 karma

Get laid on the road?

bubblanasty38 karma

Lot lizard

olfilol33 karma

Split me open like a coconut

barben41622 karma

Just open the slot, and put whatever you want, inside.

TheTrailArtist185 karma

When you walk 25 miles a day, the last thing you think about is bangin’ hoors

kjfdlhs39 karma

I see a lot of your pictures are on the side of highways. One thing I would be concerned with if I had to walk long distances is the amount of time you'd have to spend on roads without sidewalks next to cars that are going very fast. How often are you on big roads as opposed to small roads and trails? Do you ever feel unsafe on big roads?

TheTrailArtist22 karma

I try to be on quieter country roads, or nature trails as often as I can. But sometimes I do end up on the busier roads. I always walk against traffic so you can see the cars coming. People are generally helpful too to recommend better roads for me to walk on if I ask. For a while I pushed a baby stroller of supplies which made things even trickier on bad roads. But overall, just gotta use your best judgment.

FUUUDGE39 karma

What are some of the highlights of strangers that you have come across?

TheTrailArtist221 karma

A dumpster diving woman gave me a protein shake which I drank. I stayed with a beekeeper. A complete stranger broke into tears in front of me after I explained my walk- I know that sounds over dramatic but they were an older gentleman that had just lost someone to cancer and they were really happy to hear me, a young man, living life to the fullest. It was one of the purest human connections I’ve had with a stranger, and I hope they’re doing okay if they’re reading this.

sandersism38 karma

What do you think it is that defines you as an "artist"?

I'm not being sarcastic, or critical.

Does the act of making any sort of art making you an artist? In that case, is everyone an artist? Does quality matter? Do you make a distinction between amateur artist and professional artist? If so, which one are you?

TheTrailArtist50 karma

Really good question, but honestly these are questions I struggle with myself. For a long time I was hesitant to even call myself an artist because I didn’t know what it meant. I think art is always evolving and so are each of our lives, so the definition of art itself is fluid since it’s a big reflection of society.

I don’t really make a distinction between amateur and professional. I think that’s a slippery slope if you compare to each other’s too much. We all create art of some kind when we are young but a lot of people stop one reason or another. So I want to encourage every artist to create things if that’s what brings them joy.

Dubjunke30 karma

I have a buddy that's making the same walk. He just passed the Rocky Mountains. Have you seen his story or followed anyone else making the walk?

TheTrailArtist46 karma

I am familiar with him! I see posts about him on the ADT Facebook page occasionally. I was lucky to meet one ADT hiker, Colleen, as we both started walking around the same time. She kept going and has since finished while I chose to winter in Iowa.

cualina28 karma

Do you think this improved your imagination when it comes to art?

TheTrailArtist46 karma

Absolutely. My art style bounces from realism, expressionism, and surrealism. But being out in nature and experiencing the landscapes, wildlife, and people is amazing creative fuel. I also have a lot time left to my own thoughts and daydreams.

The_Girdle_of_Kirk27 karma

do you realize, statistically speaking, when you reach the west coast, you will be hit by a car?

TheTrailArtist19 karma

I know that’s a risk, but there’s risks in everyday life too. I try to use my best judgment.

DuppyBrando1924 karma

Why walk? You could do it a lot faster if you ran

TheTrailArtist17 karma

I’ve never been much of a runner, and I carry too much weight to reasonable run unless I really switched things up and had a support vehicle or something.

HackinBritBlythe21 karma

Has anything weird, creepy, or unsettling happened to you?

TheTrailArtist63 karma

I stumbled upon a falling down house in the middle of West Virginia. There was a huge thunderstorm that night and I was nervous about black bears, so I took a chance and spent a night in that place. After making sure there were no other squatters or meth labs, I looked around, curious for clues about who used to live there. The only possessions in the entire house were shoes, but no pairs. About a dozen shoes, all different sizes, including baby shoes. Besides that there was a single page of the Bible covered in dust. It was kind of unsettling sleeping there, but hey I survived.

brieslew18 karma

Do you travel armed?

TheTrailArtist22 karma

Just bearspray and a camping knife. To each their own, but that suits my needs!

snorlz18 karma

have you always looked like a dad or is that a result of the walking?

TheTrailArtist46 karma

Hi hungry, I’m dad

HurricaneMagen14 karma

What do you miss most?

TheTrailArtist55 karma

My girlfriend. We make it work and she supports my endeavors, but i won’t pretend that part is easy.

Shub740914 karma

Do you have any plans for visiting any other nation?

TheTrailArtist31 karma

Absolutely! All depends on budget, but I’d love to continue traveling. Besides the USA I did visit Canada for about a week via greyhound bus which was rewarding in its own way. I’ll have to decompress after this journey but I’d love to see where else my feet can take me.

EarlvinJohnson12 karma

Have you lost a lot of weight??

TheTrailArtist13 karma

Surprisingly I stayed just about even!

DongleNocker12 karma

What is your favorite shoe insert?

TheTrailArtist6 karma

I’ve used a few cheap ones from Walmart but honestly don’t even remember the brands!

BattleFarter10 karma

Have you almost found yourself in a serious accident/mugging/overall dangerous situation/etc?

TheTrailArtist17 karma

I’ve had some situations that made my hair stand on end, and I try to listen to my instincts. I had a guy who kept slowly driving past offering me rides after I clearly explained I wasn’t hitchhiking... I had a stalker on the trail for about a week... mostly people have been super friendly though. The biggest overall dangers have been storms, and aggressive off leash dogs. I carry pepper spray usually, or bear spray when I’m in bear territory.

cocainebubbles5 karma

On trail for a whole week?

TheTrailArtist20 karma

Yep. On the c&o canal towpath. It is a developed trail with a primitive campsite every 10 miles or so. So someone camping next to you isn’t that unusual. But it is unusual when a man on a bicycle that should be able to cover a lot more miles than someone on foot shows up every night out of nowhere to rant about strange things and gives you food poisoning. I had to ditch him through a detour and never looked back haha.

amandapanda61110 karma

Have you done the Camino de Santiago, or is that a goal?

TheTrailArtist20 karma

It’s absolutely on my bucket list. But nope, this is my first stint of long distance hiking!

kurtmaia7 karma

Do you expect the next part to be harder or easier?

TheTrailArtist5 karma

I think a bit of both. Harder terrain for sure compared to these fast Midwest states. But on the other hand I already have my routines down and know what to expect, and the first half has made me a bit wiser on how to deal with the weather, navigate, and important skills like those.

CatTattoosOnBoobs7 karma

Do you have a website? I'll buy one of your pieces after that trek

TheTrailArtist6 karma

Hey there! Feel free to follow along my Facebook or Instagram linked above.


Why did you decide to start in Delaware?

TheTrailArtist27 karma

Hey there- so I was roughly following the American Discovery Trail which goes from Cape Henlopen Delaware to San Francisco CA. I wanted to make it coast to coast for a full experience. I decided to go east to west so I could face some flatter states to build up my legs before facing the Rocky Mountains.

diatonicnerds4 karma

Compared to your perception from before you started, does the country seem bigger to you now that you are experiencing every step of its width? Or does it seem smaller knowing that you can walk across it?

TheTrailArtist11 karma

I feel both at once, it’s a really weird feeling.

FarragoSanManta4 karma

I have always wanted to do this myself but could never find information nor the courage.

If one were to decide to do this, where would you tell them to go/look to get all the info they would need and be prepared for such a journey?

TheTrailArtist6 karma

There are lots of good YouTube videos and blogs to look at! That’s exactly how I started researching when I started to feel the call. In fact it was an AMA from another hiker that really gave me confidence before I started my hike. If anyone is serious about doing a long distance hike and has more questions feel free to send me a personal message.

Cookingrawmeat4 karma

What makes you different than the dozen+ people who did it before you?

TheTrailArtist16 karma

Just because something has been done before, doesn’t mean it’s not worth doing again. This is just something my life really needed, and I want to be a spokesperson to other dreamers that ordinary people can break out of routine and follow through with their goals.

Kooper2084 karma

Is this what you thought being an artist would be like?

TheTrailArtist6 karma

I think every artist has their own story, and for whatever reason this is mine. Exploring nature and creating things have always been my passions, and this is my way of bridging those.

PettyLikeTom3 karma


TheTrailArtist12 karma

It’s really hard to pinpoint a best thing. But as far as friends, I’d like to think so! I made amazing connections with some people I still stay in touch with. Amazingly I met a woman doing the same walk with her dog, and we walked together for about a week.

Cometstarlight2 karma

Have you seen many animals?

TheTrailArtist4 karma

You betcha! Plenty of deer, turkey, coyotes, foxes, turtles, salamanders, snakes, raccoons ect. I’m looking forward to more wildlife out west.

My favorite wildlife encounter was a fox sniffing his nose right outside my tent, pushing his noise against the fabric.

Angel_Avenger2 karma

With all that walking, do u play pokemon go? If not, Im sure you could find interesting stuff on the way.

TheTrailArtist6 karma

Haha I do admit I played on occasion, but it was a drain on battery which is precious when your phone is your map, camera, and connection to loved ones.


How are you getting home?

TheTrailArtist2 karma

Hitchhiking or bus probably, depends on my remaining budget at that point and how adventurous I’m feeling haha. Flying might be too expensive because it’s hard to predict too far in advance when I’ll reach my destination.