Appalachian Trail Challenges

*Warning Endless Hyperlinks Below

Day 34 of the #VirginiaTomatoChallenge and Yes, I carved it into the tomatoes

Day 34 of the #VirginiaTomatoChallenge and
Yes, I carved it into the tomatoes

The Appalachian Trail is a challenging thing to hike. That’s not an opinion, this is an indisputable fact. Placing one foot in front of the other five million times is an impressive thought. Now add to that thought that during those five million steps the hiker will gain and lose over 515,000 feet of elevation. In that same bowl add the freezing cold nights, sweltering summer days, humidity so thick you can taste it, creepy hobos encountered, wildlife, and the occasional lack of water. The contents of that bowl start to look like a monstrous Sweeney Todd creation. So why would anyone want to make it harder on themselves?

For me, it was the same reason I hiked the Appalachian trail: to say “I did that, I pushed myself and I survived”. Just as some people at an overlook walk over to see the view, I accepted challenges because that was a part of the thru hiking culture I wanted to be a part of.

Going into my AT hike I never heard about these “challenges”, but somewhere in New Hampshire about a month in I heard about the “Four State Challenge”. The four state challenge requires the hiker to “hike” a span of 44 miles in 4 states in a 24 hour period. The states are PA,MD,WV and VA.

The first time I heard of the four state challenge it sounded crazy. I was like “that sounds like fun…if your other hobbies include hating yourself and imagining how much better life would be with nubs instead of feet, but it’s not for me”. Then as always, I thought more, and decided without a doubt I would do it, just to see if I could.

Now in reality you aren’t hiking too much or at all really in PA or VA, as most people start right on the edge and finish right over the border, but the point is you walked in 4 states in one day and it wasn’t some LAME four corners bullhonkey (IM CALLING YOU OUT CO, NM, AZ, UT). What does one “get” for finishing the four state challenge you ask? For me it was a sense of accomplishment, and very sore feet. Nothing too tangible though, just another thing to “enhance” you’re experience and make it your hike.

If you brag about walking into 4 states here, I shall scoff

44 miles in a day not your cup of tea you say? Well here are some other challenges I heard about.

A List of Challenges

*this is by no means an extensive list and is just me trying to list the ones I remember

4 State Challenge: Hike 44 miles from PA border, through MD and WV, to the VA border in 24 hours (My Four State Challenge Video)

Connecticut Challenge: Hike all 52 miles of Connecticut in one day (My favorite post from my Connecticut Challenge) (Full Connecticut Challenge Playlist)

Snickers Bag Challenge: Hike all the way through “The Whites” only carrying a 5 pound bag of Snickers bars. Challenger relies on hut system and yogiing from day hikers.

Mount Moosalaki dress challenge: hike Mount Moosalaki in a dress

Fire Tower Challenge: Go to and climb every fire tower listed in AWOL guide (*when possible)

Marathon Week Challenge: Average at least 26.2 miles for a week straight

The 7 second challenge: Ride a Grayson Highlands Pony for 7 seconds (*Not saying you should do this, just stating that it exists)

The 24/24/24 Challenge: Hike 24 miles, Drink 24 beers, in 24 Hours

Presidential Challenge: Hike over the “Presidential” mountains that the AT skirts around.

M.Y.O.C. (Make Your Own Challenges)

Don’t stop there however, make your own challenges. One day I was sitting, a month into my hike, thinking of the monstrous state of Virginia and its famed duration of 540 miles. Then a dumb idea popped into my head “what if every day in Virginia a person had to eat a fruit”. This idea pin-balled back and forth in my mind every day as I refined my idea. I thought what food would be difficult to eat AND carry for about a month straight. Tomatoes became my fruit of choice as I realized that they are ridiculous to carry because of their 1.high water weight 2. Extremely fragile nature and 3. The fact that they do not taste very good. That is how the Virginia Tomato Challenge was born.

Virginia tomato challenge

The Virginia Tomato (fruit) Challenge:

Step 1: Eat 1 tomato each day the hiker is in Virginia

Step 2: On the last day in Virginia the challenger must eat as many Tomatoes as days spent in Virginia.


Day 6 of the #Virginiatomatochallenge


The other challenge I made up was in reaction to all the things I had heard about the shelters in Georgia. There were 2 consensus of the Georgia AT shelters: They are some of the furthest off trail of all AT shelters, and the water sources are too far away. In reaction, I created the Georgia Shelter Challenge.

Georgia Shelter Challenge: Spend the night in all 12 A.T shelters in Georgia. (Georgia Shelter Challenge Pictures)


Blood Mountain Shelter during the Georgia Shelter Challenge

My point is, if you don’t like the existing challenges, make your own. I wanted an eating challenge, that’s why I created the #virginiatomatochallenge.

For you naysayers, someone on my AT blog ( once detracted from my MYOC challenges by saying “the tomato challenge, shelter challenge, those are and were in your head, those don’t exist.” To them I say even the famous Four State Challenge was just a thought in someone’s head until they did it.So if you feel like 2185 miles isn’t challenging enough, make your own challenge. If you see a gap in existing challenges, make a challenge in response to that. And if you feel like carrying tomatoes on your back for 25 days, do the #VIRGINIATOMATOCHALLENGE

Know one I did not mention? Comment below and tell the world!

Day 15 of the Virginia Tomato Challenge at the James River Footbridge

Day 15 of the Virginia Tomato Challenge at the James River Footbridge

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Comments 6

  • SoniaButton : Feb 24th

    I’m going to accept some of these challenges, and raise the one tomato a day to two.

  • Shawn Carlson : Feb 25th

    I believe your ability to cut tomatoes in different shapes is impressive enough

  • Dan Thornton : Feb 28th

    A thru-hiker last year told me he was doing the Waynesboro challenge. He explained it was to hike the 250 miles from Waynesboro, VA, to Waynesboro, PA, with no resupply.

    • Christopher LeBlanc : Mar 1st

      I like this, thats SO good

  • Eric Batson : Mar 30th

    Going to combine the 4 state with 24/24/24… so a 4/24/24. Maybe not as healthy as tomatoes but I’m willing to bet after 43 miles and 24 beers I won’t care


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