Great Barrington Hike: Day 105 Adventure on the Trail (2026)

Day 105 of the Appalachian Trail: A HERO's Journey

Today, I awoke at 5 am, eager to hit the trail by 6 am. It's been a challenging journey so far, and I needed a good night's sleep to prepare for the upcoming challenges. The trail has been a test of endurance, and I'm determined to make the most of it.

The morning hike to Great Barrington was a breeze. We covered 3.5 miles of flat terrain, alternating between pine trees and open fields. The humidity and bugs were relentless, but we persevered. We arrived at the road crossing at 7:15 am, and to our delight, we found trail magic in the form of a cooler of canned coffee drinks. We refueled and hitched a ride into Great Barrington, thanks to a kind soul named Riley.

In Great Barrington, we resupplied our packs and indulged in a delicious breakfast at the Great Barrington Bagel Company. I treated myself to a bacon, sausage, egg, and cheese bagel sandwich, paired with a cinnamon roll. We stayed a bit too long, but the experience was worth it. As we prepared to leave, we extended our thumbs for a hitch back to the trail. Within minutes, a friendly blue pickup truck arrived, and we were on our way again.

Back on the trail, we followed the Housatonic River for a mile before embarking on a steep climb. The humidity was oppressive, and I quickly found myself drenched in sweat. As I ascended, I narrowly avoided stepping on a snake that slithered off the trail. I reached a road crossing and encountered Pokey, who offered me a Gatorade and a snack. He shared valuable information about the upcoming trail sections.

The climb continued, and I battled a swarm of gnats that flew around my face. Despite the annoyance, I persevered and reached the top. I walked along the ridge for several miles before taking a break at 10 miles. The gnats persisted, but I pushed on.

One of the most intriguing features of the day was Ice Gulch, a narrow canyon that ran alongside the trail. I continued hiking, passing by a small beaver pond with two industrious beavers. The trail then led me to my second significant climb of the day, which lasted several miles. I had a few decent views, but the primary focus was on battling the bugs and my own sweat.

As I descended, I surprised a medium-sized black bear sprinting away. I managed to capture a glimpse of him before he turned around and gave me a look. I continued down the trail, still mobbed by gnats, until I reached a water source. I filled up my water jug and prepared for the final stretch.

The trail led me through a pine forest, and I descended towards the Shaker Campsite. I received a text from Shooter, informing me that he and Birdie were moving on. I decided to follow suit, knowing I had a mile of easy hiking ahead before a 500-foot climb up Tyringham Cobble.

The climb was easier than anticipated, and I reached the top without much difficulty. The views were limited, but I felt a sense of accomplishment. The descent was swift, but I had to navigate bog boards, which were slippery due to the sprinkles. As the sun began to set, I slipped off two of the boards, adding another chapter to my hiking in the dark adventures.

Day 105 Stats:
- 23.1 miles covered
- 4,541 feet of ascent, 4,344 feet of descent

I ended the day with a sense of satisfaction, knowing that I had conquered another challenging section of the Appalachian Trail. The HERO in me was proud, and I looked forward to the adventures that lay ahead.

Great Barrington Hike: Day 105 Adventure on the Trail (2026)
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