Hiking down Stratton Mountain I felt elated and completely at peace. A couple miles from the summit I saw a couple hikers setting up hammocks just off the trail. Enjoying the relaxing pace I had adopted this evening I sat down for a minute to check my mileages on my phone and ask them about the trail conditions down the hill. As was becoming the norm they couldn’t believe I was camping with such a tiny pack. Both engineers from Boston, they asked where I was from. I told them Richmond and one of them said he was dating a girl in Richmond. I found out she went to a rival high school and graduated a year before me. Simple things like that bring back little pieces of home and made the trip much more bearable. It was a cool little reminder of the connectedness in this world. In my loneliest moments, I always found there was a little bit of home everywhere, whether in some familiar looking woods, or in a phone call home, in a stranger’s friendliness, or in a crazy connection.

I continued another couple miles, hoping to camp just above the mosquito infested marsh all the way at the base. But I hiked too far and felt the brunt of the biting bastards as I tried to go to sleep under a darkening sky. I covered my hands with Deet, wore my wind jacket, and with my headnet on tried to ignore the constant buzzing in my ears. One of the catches of carrying only 3.5 pounds of gear is that I had to pick my campsite with tremendous caution and consideration. It would never be perfect, but I always ensured it wasn’t going to be dangerously cold, wet, or horrendously uncomfortable. Tonight I let my tarp stay in my pack and camped under the stars. But I was asleep before they appeared.

I felt it again in the middle of the night. I woke up and grabbed my stomach, crippled from the cramps that radiated all over my abdomen. The entire day had been without a hitch but the nausea that plagued me last night had returned. I had deliberately not eaten when I arrived at camp for fear that my indulgence last night was what caused the illness. But apparently that wasn’t it. Tonight, however, I feared for losing more calories, and truly couldn’t afford to expel them, even at the expense of losing some more sleep to have my stomach settle down on its own. It took over an hour but eventually it did. I had suppressed the gagging and fell back asleep, uncomfortable, but tired enough to ignore it.

The nausea didn’t return and I suspect I’ll never know what caused it. I woke at sunrise, and with no tarp to break down was hiking within minutes. The coolness of the night had put the mosquitoes to rest so I had enjoyable, easy hiking to start the day. My goal was to make it to Williamstown, Massachusetts to resupply and hopefully get a night in a bed.

By late morning I was on the summit of Glastenbury Mountain with crowds of section and day hikers, a stark reminder that the weekend had begun. I had rolled into the shelter just past the summit of this mountain in 2009 late in the day before my first exceptionally chilly night of the trip. Temperatures dropped into the teens and snow fell throughout the night. Today on the other hand I was dripping sweat in the summer heat. It reinforced how dramatic the difference between two hikers experience’s can be. Even individuals hiking together see the trail in a different light, look at different things, experience different moods, hold different biases. Since I began these fastpacking adventures after my failed winter thru-hike attempt in 2009, I have struggled to understand my enjoyment of this style over the traditional distances most backpackers hike. But no two hikes are the same, and no two hikers come to the woods for the same reasons. It is an intensely personal endeavor to attempt a thru-hike and I try to not be critical of anyone’s reasons to come out into the backcountry.

Later in the day I realized that any minute now I’d be running into Scott Jurek, the runner battling for the supported record who was heading northbound. I had no idea when I would see him but I knew it was soon. Down in the valley I crossed a road and began working my way back up the ridge. The climb was extremely steep but nothing exceptional after dealing with south Maine and the White Mountains. With sweat dripping from my brow, I exchanged greetings with a nice family taking a rest halfway up the climb.

Up on the top I came upon an older man likely out for a section hike, and I honestly think he was the first sincerely grumpy person I’ve met out in the woods. He asked me if I knew how far back Harmon Hill was. I told him I was unsure what that was but he apparently didn’t like my answer. I told him I came up a steep climb a couple miles back and that might be it. He looked at me, took a step closer, getting his face within a foot of mine, and enunciated each syllable “HAR-MON HILL” treating my like I was deaf or dumb instead of someone who possibly has better things to do than memorize the name of every bump on the Appalachian Trail.

In disbelief I kept my politeness and told him, “I’m sure that is it, just up the trail,” as he stormed off without acknowledging I was continuing to answer his question. I couldn’t tell you what it was exactly that pissed him off so much but I was in total shock. I happened to be in a good mood though so I shook it off and kept hiking. In any case, meeting an ass in the woods was the least of my worries. The biggest challenges on the trip were not the things out of my control but the issues I actually had to deal with. I put it to my mom that someone could throw a softball at my face as hard as they could and I wouldn’t care one bit. But running out of food and having to hike 15 miles on an empty stomach, or meticulously pitching my tarp in the rain for comfort rather than rushing it to lay down sooner; those were the challenges that overwhelmed me.

Late in the evening I was approaching the Vermont-Massachusetts state line and in another episode of Grayson-naivete, let my phone battery die rocking out to The Glitch Mob on my headphones. I had already looked to see which direction I needed to turn down in the valley to go resupply but still would have prefered had my phone to double check. I always checked about 10 times which way I needed to walk down a road to get to the hotel or restaurant or resupply. With some of the walks nearly a mile long, that would be absolutely devastating to my sensitive and exhausted self to walk the wrong way and have to turn around.

After crossing on to the Massachusetts Appalachian Trail section, I started my descent down toward the town of Williamstown. As I was heading down I could hear noise in the valley, definitely a festival or concert of some sort. I heard sirens and the distant sound of cheers and music too faint to make out. It would come and go as I dipped in and out of little valleys and over small ridges. But as I got closer and closer the sounds became definite and with it my realization of what that meant for my hopes of sleeping in a bed tonight. For the next few miles I hoped and I hoped that something within walking distance would have a place for me to stay. The clouds were rapidly rolling in and I knew persisting rain was about to start.

A mile out from the road the rain began to fall and I donned my homeless man outfit to keep me warm. At the road I headed west, and asked a guy approaching on a walk with his dog if I was headed the right direction to get to the Papa Johns. My legs ached and tibialis anterior tendinitis had locked out my right leg.

I gimped into town and headed over to the closest hotel to see if they had any rooms. Totally booked. As with all the rest of them within walking distance. I’ve had a lot of demoralizing moments on my adventures, and this trip was no different. To hike a 42 mile day to sleep in a bed and dream of setting a 16″ pizza down and watching trashy TV with a pint of Ben and Jerry’s for dessert only to find I’ve happened to arrive during a huge semi-annual Wilco music festival is about as demoralizing as it gets. Like an attentive mom I kept checking in with myself. I was keeping it together for the moment but I thought any minute a less composed side of me may just throw my trekking poles, start kicking the ground, and having an adult temper tantrum like the world has never seen.

I walked away from the motel, rain creeping in through the sides of my poncho, no clue of where I would spend the night and certainly no desire to walk all the way back to the trail and then have to hike even further to find a campsite. I headed for the Papa Johns and neighboring grocery store right across the street. I continued checking in, “Are you okay Grayson?” and in a tremendous fit of denial kept acting like I was totally okay. I ordered a 16″ pizza and cheesesticks and went shopping for my resupply while I waited. When my pizza was ready I sat on the small bench inside where most normal people may sit for a couple minutes waiting for their pizza to be ready. But I ate, and unpacked my trash, and charged my phone, and packed up my new food. By the time I was done it was nearly 10pm and I was so exhausted I wasn’t sure I could make it out of town without collapsing and falling asleep.

I’m not exactly sure if my blank emotions were the result of a hardened man or a broken one, but either way I was still out here, still moving.

But I put my poncho back on, grabbed a pint of Ben and Jerrys from the grocery store, and walked out of town, winds raging, throwing water right through my poncho and soaking my down jacket beneath, trekking poles strapped to the top of my pack, eating a pint of ice cream. The road walk out of town dragged but gave me ample opportunity to finish my dessert and throw away the trash in an elementary school dumpster before entering back into the woods. The trail was slick soaking wet clay and I slipped and slided on the gentle climbs and nearly fell on the descents. I didn’t make it far, and most people would never have considered where I slept a campsite. I had a large root under my right hip, the ground wasn’t even close to flat, and the watery mud beneath me was sure to get all my gear disgustingly dirty.

I lost a stake while setting up camp but kept my composure long enough to build a solid tarp. I made myself as comfortable as possible and was asleep within minutes. It ended up being my longest day, at over 44 miles including the walk to the resupply, but only 42.3 trail miles. Wet, cold, covered in mud, and bitterly unhappy, I had kept myself together despite a seriously disappointing night. I’m not exactly sure if my blank emotions were the result of a hardened man or a broken one, but either way I was still out here, still moving.

Continue reading: Day 20