Hi Outdoorwanderer - what an incredible adventure you've had. I'm jealous. And I enjoyed reading about the beginning of your journey.
I have a few suggestions having read these first two chapters:
I would consider making your opening paragraph more impactful and inviting for the reader. Rather than opening with 'My story starts 10 years ago...' which is a bit flat, you could start by describing the view from the Mt. Katahdin. Suck the reader in with the fabulous view, then back track to the fact this was ten year ago and was what started you on your quest. Share the moment with the reader.
This is something I feel you could apply throughout the story. Show don't tell. For me it feels a little too factual at the moment, when what I want to be doing is experiencing what you saw and felt. There's going to be moments when you need to fast forward (I thought this was very well done: The next day was pretty uneventful. Eat, sleep, hike, poop, and be sore as hell. Like no joke, “Embrace the suck” is the mantra of the trail.) But for the rest of the time try and show us this experience a little more.
I'd also suggest trying to think of each chapter as a mini story in itself. Work out what were the highs and lows of that leg of the journey, and concentrate on them. I think that will help to lose the tone of 'then I did this, then I did this...' And will help you to weed out some of the unnecessary and not so interesting detail. (Have to say, I really wanted to know what that canoe trip across the river was like, but you just jumped across to the other side and to a shop.)
I hope the above thoughts might be helpful, but ignore if the don't tie in with the tone you're going for. Good luck with the editing.