Reader Essays: My First, Worst Trip

New to hiking? Brian Simpson 
has a foolproof plan for doing
it all wrong. 

On a hot summer weekend about five years ago, my college buddy, Joe, and I decided to backpack the Knobstone Trail in southern Indiana. Well, it was my idea actually, so I’ll take 90 percent of the credit … er, blame. I know southern Indiana isn’t exactly the first (or even tenth) thing that comes to mind when you think of difficult hikes, but trust me—this one is hilly. The route goes up and down (and up and down) the Knobstone Escarpment. I suggested we do all 50 miles in two days, and Joe agreed since he didn’t know any better.

I woke Joe up at 3 a.m. and we hiked by headlamp for a while. I didn’t want us to take long rest breaks, since we needed to hike at least 25 miles before nightfall, so I kept us moving. This quickly earned me the nickname Drill Sergeant Simpson. I should mention that this was Joe’s first real backpacking trip, so, in retrospect, 50 miles in two days in hot weather maybe wasn’t the best idea. Neither was Joe’s trail diet of Skittles and dry pasta (you pack it in your cheek like chewing tobacco). It caught up with him at about 20 miles. That’s when I heard a loud WHAM! behind me. It was the sound of Joe’s body hitting the dirt face-first.

We quickly determined that we needed to hike to the road and hitch a ride ASAP; Joe was done hiking. It was three miles to the next trailhead. Joe tore off like a rocket and I had trouble keeping up. I caught up with him when he blazed to the top of this hill that required handholds to get up. When I finally got to the top, Joe was there sitting on a stump. He asked me how I was doing, and then he promptly threw up, producing a stream of red Gatorade-colored liquid that jetted approximately 56 feet. 
We eventually reached the trailhead, where I called for a ride and Joe passed out. Two dogs from the nearby farmhouse waited with us; they licked Joe every 15 minutes or so, when he’d wake up, roll over, and get sick. 
Joe ended up spending several days in the hospital due to severe dehydration. I felt bad, but being the all-around good guy that he is, Joe readily forgave me. In fact, he has actually joined me on many more hiking trips. He even conquered the Knobstone Trail—without feeding the dogs. 

Simpson lives in Sebastian, FL. Favorite hike: Sliding Sands Trail in Haleakala National Park, HI.