Eddie O'LearyComment

Days 98-101

Eddie O'LearyComment
Days 98-101

    After crossing into Massachusetts, I stopped into Great Barrington, a touristy town with some tasty food choices and of course, ice cream! Great Barrington also has a community center which allows hikers to camp there, free of charge. So that’s where I, Tiny Tim, Songbird, Footprints, Ringo, Young Buck, and a few others spent the night. Tucked away in the trees, we stayed up way too late chatting and drinking beer. In the morning, everyone decided to take a zero day, but I headed out. I was meeting my friend Mike in a few days, and hoped that by hiking ahead a bit, I would meet back up with everyone later. True to AT form, I couldn’t head out of town without an unexpected, bizarre experience.

    I was showering in the community center when I heard my name. It was some random guy who I had never met before. He came over to my shower (mind you I was naked) and asked if I could help him set up a tent for 25 bucks and lunch. Sure! Sounded simple enough. Ringo and Young Buck came along as well. We figured it wouldn’t take too long. I could hit the trail with plenty of daylight left. 

    Nope! Forty minutes on a rugged, dirty road later we wondered if we were going to survive. This 60 year old guy hit on every girl that breathed, acted like a 16 year old boy, told cringe-worthy dirty jokes, and bragged about tales of bar fights. “I’ve been in over 350 fights in my life. Don’t worry only 50 of them were street fights.” Sure seemed like a perfect set up for a horror film. There were three of us, so we weren’t really to concerned. But we did exchange knowing looks. 

    We finally arrived expecting to set up what we thought would be a party tent or something similar. Nope!  It was a gigantic mess of canvas that looked like a circus tent. Turns out this guy plans on living in this tent. It was so awkwardly designed that it took the four of us 45 minutes to get it set up. Oh yea, and look out for the hornet’s nest in the ground! (Thankfully only crazy guy got stung.)

    Forty minutes back to town and a lunch later, it was early afternoon. Later than I had wanted to start, but still not too bad. I tell crazy guy to drop me off, and before I could grab my pack out of the bed of the pickup, he drives away! Literally everything but my phone and wallet were in that truck. Everything! Holy shit. That could be the end of my hike.

    So what does one do when someone drives off with your pack and you have no clue how to get it back? You go to the coffee shop, get some cold brew, and think. Coffee in hand, I ran through my options. Ringo was going back to the community center. Maybe he would notice my pack and grab it. I didn’t have his number, but I could walk back and see. That was about the only thing I could do. So I embarked on a 2.5 mile road walk to the community center on a hope and prayer. Along the way I stopped at a donut shop. Next I stopped and grabbed a pizza, because why not. One donut and one pizza later, I arrived at the center. Ringo was there… and so was my pack!

    Crisis averted, I did the only thing that seemed logical. Grabbed a beer at the brewery next door with Tiny Tim. I still wanted to hike out, but by now it was late afternoon. I would need to find a ride back to the trail, which could take some time. Luckily, Tiny Tim had the number of a trail angel. I called him, and he gave me a ride back! I was so happy to be back on the trail.

    The first few miles of Massachusetts were some of the best in a long time. The trail finally started to feel like mountains again, reaching over 2,000 feet for the first time since probably Virginia. I stayed at Upper Goose Pond Cabin, a rustic cabin on a lake, now an official shelter. I sat on the dock that night, spellbound by the stars. In the morning caretakers, Paul and Wendy, made a a bountiful pancake breakfast.

    Fueled by all the carbs, I raced in Dalton to get to the post office before it closed where my friend Chris had mailed me a care package. Some bad storms were headed my way, so I decided to stay in town. I had heard that a man named Tom sometimes lets hikers stay in his yard. I found his house and sure enough, a couple other hikers were tented already. Since the winds and rain were pretty severe, Tom actually let me sleep on his porch!

    The next day was a big one. Day 100! To mark this milestone, I would climb Mt. Greylock, the highest point in Massachusetts. The trail was quite muddy from the previous night’s rain storm. At times, the trail seemed more waterfall than walking path, but I loved this climb. The previous 700 miles had very few real climbs, and I would be at over 3,000 feet. It felt good to feel the burn in my legs after sustained climbing. I reached the top to discover a brilliant surprise. That evening there would be a bag pipe concert! Seriously? Bagpipes on a mountain top? I could not miss this.

    While waiting for the bagpipes to start, I popped open a couple of beers that Chris had sent me, basking in the glorious sunshine and chatting with some other hikers I had just met. I also talked with a lady who seemed super interested in my endeavor.

    At 6:00 the, show started. Hearing bagpipes play on an open mountain top, the wind blowing through your hair, the sun setting in the valley, is magical. Something stirred within me, like wild calling to wild, as if to join my spirit with those notes and, together, to rush down the mountain igniting wildfires of passionate life.

    As the final notes evaporated into the permanency of time, the lady I was talking with earlier came up to me and asked where I was staying for the night. I told her I wasn’t sure yet. She then offered to take me back to her place with her husband and son. Seriously? This incredibly day kept getting better!

    At the Casey’s place, I showered, did laundry (ending my streak of no clean clothes at 35 days), hot tubbed, and ate so much food. In the morning they fixed me breakfast and took me back to the top of Greylock. 

    I have been blown away by people’s generosity and kindness. In a world where so much of what we hear is bad, there is so much more good. It’s all around you, but no one’s saying anything about it. Be open to those around you and be encouraged that little things go a long way. You’ll never know how you might change someone’s life.



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.