Preston & Steve®

The famous Appalachian Trail is 2,190+ miles of scenic views, freezing nights, and sweltering hot days. The path runs between Springer Mountain in Georgia and Mount Katahdin in Maine. From south to north, the trail passes through a total of states: Georgia, North Carolina, Tennessee, Virginia, West Virginia, Maryland, Pennsylvania, New Jersey, New York, Connecticut, Massachusetts, Vermont, New Hampshire, and Maine.

The Trail is free to walk along, although it does pass through a few parks which charge fees or require permits to camp out.

A recent article in Philadelphia Inquirer got us talking about infamous journey that thousands of people embark on every year. The newspaper’s feature was about the tough terrain hikers endure during the stretch of trail through Pennsylvania.  The 229 miles through PA have been nicknamed “Rocksylvania,” a.k.a. “hell,” “the meat grinder,” “the ankle roller,” a place where hiking boots go to die.”

But there is a positive spin to this nightmare! We learned that to conquer the nearly six-month adventure, true trail connoisseurs also partake in a series of different silly challenges. 

MMR listeners told us about one challenge that takes place along the most dreaded section of trail in Pennsylvania. After hearing about this challenge, it made us interested in what other dares accompany the trail. 

Some are sanctioned challenges, and some are only word of mouth (or word of Reddit, blogs, etc.) Read on and maybe get inspired.

  • Half-Gallon Challenge

    The “Half-Gallon” Challenge namely takes place at the halfway point of the trail, which falls at The Pine Grove Furnace General Store in Pennsylvania. 

    The rules of the challenge? Simple, eat a half gallon of Hershey’s ice cream. The challenge originated in 1980, but it is still one of the many quests the trail offers. 

  • Snicker Bag challenge

    Many Appalachian trail hikers recommend Snickers as a trail treat. But this challenge tasks you with carrying only a 5-pound bag of Snickers all the way through the White Mountains of the trail. 

  • 24 X 24 X 24 challenge

    If the trail wasn’t difficult enough for you, try doing it drunk. The mission of this challenge is to drink 24 beers while hiking 24 miles in 24 hours. There are multiple different strategies to beat this challenge, from drinking it all in one sitting to pacing yourself throughout the day. But is there really a winner with this challenge? 

  • Four State challenge

    Four states, 24 hours. Sounds fun, right? The greatest difficulty with this is the mileage you need to cover to complete the challenge. That is 42.6 miles to be exact. The terrain apparently makes it not too difficult, but 40+ miles in one day does not sound pleasant to us.  

    The Four State Challenge travels across the borders of Virginia, West Virginia, Maryland, and Pennsylvania.

  • Mount Moosilauke dress challenge

    This challenge is quite self-explanatory. Hikers are contested to wear dresses as the hike up Mount Moosilauke.

Sign me up for the MMR VIP email newsletter!

Get the good stuff sent straight to your inbox, and be the first to know: concert presales, exclusive contests, and behind the scenes photos and video.

By clicking "Subscribe" I agree to the website's terms of Service and Privacy Policy. I understand I can unsubscribe at any time.