Massachusetts And A Series of (Un)Fortunate Events

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The first day of Massachusetts, or “Mass” as people call it (and I adopted because I think it makes me sound cool) was full of surprises. As previously mentioned, the mud that had been very prevalent in Vermont, suddenly vanished in Mass. Well that was a lie. It was just as muddy, only a different kind of mud. Where as the Vermont mud was deep and dense, the Mass mud was slippery and treacherous.

A possible future residence

Anyway, after trudging through the mud for a while I came upon another southbounder, Dirty Dan. A Minnesotan canoe paddler turned thru hiker. Together we walked into North Adams. Or the outskirts of it. Half a mile from the road crossing was a grocery store. With the promise of fresh food, we headed in that direction.

I walked through the store for what must have been 2 hours, trying to decide on what to get for resupply and for shoving my face immediately. Sometimes the options of a well stocked store is overwhelming, seeing that you’re only able to buy what you’re willing to carry. In the end, I decided on getting too much food.

I sat outside the store with Dirty Dan, Spirit and Sun Chaser, among several northbounders who came and left. Eventually, after eating big dent into the food supply I’d just gotten, it started to rain. Just another reason to postpone hiking out. As we were sitting there, several people came up and wished us good luck.

Here’s where it gets interesting. After a while of sitting outside the store, a friendly looking man comes up to us, stops to ponder for a moment before going: “So here’s what I’m going to do, I’m gonna go in, get groceries for dinner, take you all back to my house and make you dinner. You can stay the night and in the morning I’ll make you breakfast before driving you back to trail. How does that sound?” Naturally we couldn’t refuse an offer like that, so we accepted, gladly. John, as the man was named, gave me $20 dollars to go into the liquor store and get us all drinks for the night.

We packed John’s car and drove back to his house in the next town over, South Williamstown. John’s house was located on a large property with a good view of the surrounding mountains. But get this, the house is from 1760! That’s older than the United States! In awe over the house and the entire situation, we unloaded the car and carried everything in.

In preparation for dinner at John’s

At John’s we met Drop Bear, from Australia, who’s here to hike a bunch of cool trails. She Hiked the AT in 2015

I helped prepare dinner, chopping veggies that John had grown in his garden. We all got to shower before dinner and borrow clean clothes while Drop Bear washed ours.

Clean and happy, we all sat down to have dinner. Beans, bread, veggies, burgers, wine, beer. All of it. We ate until we couldn’t anymore and then we just sat, having more wine, talking about the trail and future hiking. We asked John why he was doing this, helping complete strangers, and he replied: “I have lived a wonderful life, have three beautiful children and now I just want to give back”. I considered myself lucky.

The next morning we woke up from John knocking on the door, calling us down for breakfast. We had blueberry pancakes with real maple syrup and, of course, coffee. When we were full it was time to head out. We said our thanks and goodbyes to John and Drop Bear. Drop Bear then took us back to the trail. Spirit wasn’t feeling well and stayed another day.

Sun Chaser, John, Dreamer (me) and Dirty Dan standing in front of John’s house

We began going up towards Mount Greylock, the highest point in Massachusetts. The trail was still muddy and a lot of the walking was not as much walking as it was slipping. Some way or another we made it to the top. In the lodge Sun Chaser and I spent several hours charging things and sitting in real chairs, feeling almost like normal people.We started walking again just before it started raining heavily. Determined to not let it get us down, we sang songs and splashed in the puddles as we walked. Having a shelter to dry out in after the rain was also helpful.

Well in the shelter there was a man who was well in on a bottle of rum. He later finished his bottle and passed out. As everyone in the shelter was falling asleep, we heard a gushing sound standing out from the monotonous tapping off the rain. The drunk man was peeing in the shelter. Luckily it was one with bunks and he was on the lower one. So it didn’t directly… affect anyone. Thankfully those sort of thing are mostly unheard of otherwise.

The following day we made it into Dalton, another town that the trail goes right through. I picked up a pair of sandals to try to hike in, seeing that I hadn’t been fully satisfied with my shoes. Only miles will tell how well they work.

The Legendary Simba


A man named Tom lets hikers set up camp in his yard in Dalton. He’s been doing it for 39 years! There are no toilets in the area however (this will be relevant in a little bit). So we set up our things and sat for a while before Simba showed up. Simba who I hadn’t seen since Washington on the PCT last year! He drove 6 hours from Pennsylvania to come visit me. Simba, Sun Chaser and I spent the evening eating pizza and talking about everything hiking. Spirit showed up later and we all did a late resupply run to Walmart. It got late and we went back to Tom’s backyard and fell asleep. At least everyone else did.

If you’re sensitive to poop stories, stop reading now… I couldn’t fall asleep because of intestinal… gases. After trying for hours to fall asleep, I finally gave up and went for a walk. At 2am. In an unfamiliar town. I found a semi secluded spot and managed to dodge an accident last minute. I went back to bed and got probably two hours of sleep.

In the morning Tom got donuts for everyone. Simba, Sun Chaser, Spirit and I went for coffee before saying goodbye to Simba and hiking on.

What followed was the most strenuous day of hiking I’ve ever had. Not because of the terrain and not because of the mileage. Because of my stomach and whatever was going on in there. We started hiking at 11 and slowly but surely my stomach got more and more… unstable. I fell behind the others, having to stop every other hour, having less and less energy with each passing minute. In the afternoon I had to get my trekking pole (I only have one) and use it with both hands to get up hills. It was some of the slowest walking ever. Somehow, despite the unfortunate day, I made it 20 miles to Upper Goose Pond Shelter right before sundown. It’s a legendary place because it is housed by caretakers who often make food for the hikers. There was none left when I arrived and I don’t think I could eat anyway. I struggled to set up my tarp and went to bed, finally.

Upper Goose Pond Shelter

In the morning I surprisingly felt great. For the first time on the AT I slept through the night. I guess the mishaps and hardships of the previous day were due to food poisoning.

The trail went through pastures and fields for the next few days. A field is almost as good as getting a view, because it’s a break from the thick forest cover. Or as they call it on the trail, the green tunnel. Although it can get tiring with the constant cover, the trail is ever changing. You just have to make sure you look. Often it is the sort of beauty that doesn’t simply appear, but rather, has to be noticed. It requires a practice of appreciation that sometimes evades even the best of us. When we do look however, and especially when we see, so many spectacular things are discovered. This is something I’m working on and something that’s usually easier to remember in hindsight.

A field

The green tunnel

Oh and I saw a bear!!

The green tunnel, but different

Spirit, Sun Chaser and I all went in to Great Barrington, a popular tourist town in southern Mass and the last one southbounders can access from the AT. Sun Chaser and I hit up the Rec Center for showers and charging. Spirit had her mom visit and we didn’t see her. After spending many hours in the Rec Center, we ate at the brewery. The beer was good, but the food was meh… You know, if you ever happen to be in Great Barrington.

We slept behind the Center on wooden platforms in the forest. The next morning we procrastinated and didn’t leave as early as we should have. Sun Chaser left before me however. When I finally left I caught up to Spirit and her mom. I continued alone to a campsite by a fresh little spring, about 5 miles from the Massachusetts/Connecticut border. After watching netflix on my phone (a bad habit that’s easy to pick up when you’re in the woods for too long) I fell asleep. Early the next morning I crossed the border and entered state number 5.

Mass treated me well. It was probably my favorite state so far. I said the same things about all previous states, which means I can consider myself lucky. To have the best moment be the present one is an art and often a struggle. In a world where it’s so easy to get carried away, being able to say, and mean, that you wouldn’t want to have it any other way, is a gift.

Massachusetts was a mix of fortunate and unfortunate events and I wouldn’t have it any other way.


  1. Nick Welch says

    Nick you express everything so well I feel I’m sharing the moment. I like the point about looking and seeing and noticing, it’s a rare skill, keep honing it and reap the rich rewards it offers.
    As always take care


    • Thank you. Writing about it makes me feel like I’m experiencing everything twice, and it helps with trying to take it all in.


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