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Thursday, September 7 Next

To the trailhead

I begin on an inauspicious note—by missing my train to Pittsfield! I’m delayed on my way to the station, and arrive five minutes late. The train’s gone. Fortunately for me, there’s a Greyhound bus leaving for Pittsfield only an hour later, so I buy my ticket and settle in to wait. It occurs to me that in spite of being an avid Amtrak rider for years, this is somehow the first time I’ve ever missed a train.

I feel strangely empty after all the running and scrambling to try and make the train and then book the bus ticket. I somehow am finding it difficult to picture the trip ahead of me, maybe because I’m still in the flow of “regular life”. Doing mundane things like futzing around on my phone while waiting for the bus. I just can’t imagine what it will be like to be out there, and I don’t really feel the nervousness or excitement that I expected too.

It’s supposed to rain a lot in the first few days. That’s Vermont I guess! I’m a little worried my gear is too heavy and I should have bought trail runners instead of boots1. We’ll see.

The bus arrives, right on time, and I throw my pack underneath and get on. I feel somewhat naked without it. I’m conscious of the fact that if it were to get stolen or lost I’d be in a real bind. I listen to music while the hours slip by, and we arrive at Pittsfield Transportation Center in the early evening. I grab my pack and step out onto North Street. Pittsfield is a cute enough town, but very sleepy on a random Thursday. There’s almost no one on the street. After wandering around for a while I eat dinner at a burrito place, and then start the one mile walk to my AirBnB. I arrive and am greeted by the host, an older woman named Susan who has a spare room she rents out and an adorable dog whose name I’ve forgotten. She’s an artist and has lived in the house for 20 years, so it’s piled with knickknacks, memorabilia, etc. Kind of a grandmother’s attic vibe. Charming, but you also feel like with every step you might crush some priceless relic.

She shows me to my room, and I lay down and stare into space, not having much else to do. My phone charger just broke, so I want to conserve battery. It’s old and was acting flaky before I left, and I knew I should have replaced it before leaving but didn’t get around to it. I know I’ll probably be able to get a new one at a pharmacy in the morning, but it’s nerve-wracking to be out here all alone and be so dependent on it, especially since I don’t have a map and compass2.

As I while away the time, it starts to rain, and then to thunderstorm—hard. The house is so old and the storm so fierce that you can feel the walls shake and vibrate every time the thunder strikes. I’m also realizing my plan for getting to the trailhead won’t work. I had hoped to take an Uber or Lyft, but checking the apps there’s just no cars around here. The Berkshires has a bus system that should get me there, but I’m kicking myself because I’ll have to walk all the way back to the transportation center to get a ticket, rather than just getting on the bus stop right by Susan’s house.

At this point between the phone charger, the storm, and my transportation worries, I’m feeling pretty nervous. I’m thinking about how tough it would be to be out on the trail right now in the storm, and how muddy it’s going to be tomorrow. Before I left I read a couple posts online from people who dropped out soon after starting with packs about as heavy as mine, which makes me feel like I should have sprung for lighter gear. And in general it’s just hard to be out here on my own and not know if I have the right stuff or if I’ll be able to get it. I think I’m already finding the solitude tougher than I expected. When you’re doing something hard and have doubts, it’s worth a lot to have someone there just to support you emotionally and to be doing it together. I may be alone now, but I can think about my friends and family, who are supporting me from far away, and I can try to make friends on the trail. Remember that—the people you meet aren’t just a fun extra, they’re a big piece of support to help you get through it. Be open to connection.

This is the first time in a while that I’ve really had a goal. And it’s a hard goal at that. It’s scary to contemplate failure. Somehow it didn’t really occur to me that I might not finish until I was out here staring it in the face. But I’m glad I went for it anyway. If I had thought too much about failing and what that would feel like before I left, I might not have come at all. I don’t know if I will make it to the end of the trail or not. But I believe I can do it. I have the fitness, the focus, the perseverance. I have the backpacking skills and background deep within me, more so that a lot of people who start the trail. I just have to trust them, don’t give up, and be optimistic and outgoing. I believe in me, I got this ❤️

  1. When I started backpacking in the 2000s, everyone wore heavy, waterproof, ankle-high boots. Times have changed though, and now everyone wears lightweight mesh trail running shoes instead. You can read more about this on Cam Honan’s site. I chose to go against the prevailing wisdom and hike in my trusty old Lowa boots, partially out of thrift (I’d have to buy trail runners and I already had the boots) and partially out of stubbornness. ↩︎

  2. Another “back in my day”: a map and compass used to be the only way to navigate when backpacking. Nowadays most thru-hikers just bring their phone plus an external power bank and use an app called FarOut to navigate, recharging their batteries every few days when they stop in town. ↩︎