Eddie O'LearyComment

Days 104-109

Eddie O'LearyComment
Days 104-109

Feeling energized from my time off trail with Mike, I was eager to return to the trail. Mike dropped me back off in North Adams on a refreshingly cool day. I was particularly excited because at the top of the climb lay the Vermont border!

The first 100 miles or so of Vermont coincide with another trail called The Long Trail. In fact, a hike of the Long Trail way back in the 1920's inspired Benton MacKaye to develop plans for the Appalachian Trail. Since I was actually hiking two trails simultaneously, I met quite a few people hiking the Long Trail.

Vermont proved to be everything I expected and more. Bigger mountains, dense pine forests, and pristine beaver ponds filled the landscape. A couple fire towers climbed above the tops of the pines, providing spectacular views of the surrounding mountains. Much of this time, a thick fog or drizzle encompassed the woods, creating a somber and almost magical atmosphere. Everything was so calm and still. 

My first couple of days in Vermont, though, were spent trying to catch up to Tiny Tim and the rest of my trail family. I hiked out ahead of them in Great Barrington hoping they would catch up when I took time off at Mike's. My first night back on the trail, I learned that they were only 4 or 5 miles ahead of me. I figured I'd be able to catch them the next day or so.

I hiked hard the next 2 days and still didn't catch up to Tiny Tim. I briefly caught up to him on top of Bromley Mountain and learned that he was pushing big miles to pick up cold weather gear before the post office would be closed for Labor Day weekend. I wanted to hike at a slower pace to enjoy the Vermont woods. Everyone else was spread out along the trail, so I remained solo. 

The weather had started to cool down significantly so I was ready to pick up my cold weather gear in Rutland, about 3 days away. Before I got to town though, I experienced one of the coldest days on trail so far. The night before I got to Rutland, the temperature dropped to the low 30s. I only had a 40 degree bag and no insulating jacket! Surprisingly, I slept pretty well and didn't get too cold. In the morning, I climbed Mt. Killington amidst some ridiculous winds. Again, I wasn't too cold because I was moving. My hands however, were pretty cold and I resorted to using an extra pair of socks for gloves.

At the top of the mountain, I met a group of ladies who took another trail to the summit. Mt Killington is another ski slope and there's a lodge with food and, most importantly, hot beverages at the top. I helped these ladies find the lodge, and as a way of thanking me bought me coffee and gave me some homemade cookies!

From the lodge, I could look over mountainous landscape and just make out Mt. Washington looming on the horizon. The White Mountains lay so close! At that moment, something within me seemed to shift. It was hard to believe I had fewer than 500 miles of trail left on this incredible adventure and I wasn't ready for it to end. I was eager to explore the Whites, yet each step brought me closer to a departure of a life I had grown to love, to call home. Each step now took on such significance. Perhaps they always carried more meaning than mere motion. Perhaps they always do. Tentatively, I descended down the mountain, where a foray into the town of Rutland awaited...


I am a filmmaker. I am an adventurer. I believe in children. My friends are obsessed with my beard. I am obsessed with beer. I want to embrace and fully live this life I’m blessed with. I want to be known as someone who loves deeply.

On May 16, 2017 I set out on my dream, the adventure of a lifetime: a 2,189.8 mile trek of the Appalachian Trail. I want to push people to live their dreams and pursue their passions.