Day 105 – Great Barrington HERO (2026)

On day 105 of the hike, the hiker embarks on a journey through the Great Barrington section of the trail, a stretch known for its hot, humid, and buggy conditions. The day begins with an early start, aiming to be on the trail by 6 am. The initial hike is a quick and easy 3.5-mile trek to a road crossing, where the hiker hitchhikes into Great Barrington. The hiker expresses a sense of relief at the trail magic, including a cooler of trail magic and a ride from a kind driver. The grocery store resupply and breakfast at the Great Barrington Bagel Company provide a much-needed boost, and the hiker is back on the trail by 10:30 am, feeling energized and ready to tackle the day's challenges.

The trail then leads the hiker along the Housatonic River for a flat mile before the first significant climb of the day. The hiker notes the high humidity and the presence of gnats, which become a persistent nuisance throughout the day. The climb is steep and challenging, but the hiker perseveres, reaching the top and enjoying the views along the ridge. A quick break is taken before the hiker encounters Ice Gulch, a unique geological feature along the trail.

The hiker then embarks on the second large climb of the day, which is over several miles and offers a few decent views. However, the hiker is more focused on the swarming gnats and other bugs that accompany the climb. A surprising encounter with a medium-sized black bear adds an element of excitement to the day, and the hiker manages to capture a photo at a safe distance.

After the bear encounter, the hiker continues on the trail, filling up water sources and navigating through a pine forest. The hiker then descends towards the Shaker Campsite, where they receive a text from Shooter and Birdie, indicating that they are pushing on. The hiker decides to follow suit, embarking on the final few miles of the day, which include a 500-foot climb up Tyringham Cobble.

The descent down goes quickly, but the hiker must navigate through bog boards, which are slippery due to sprinkles. The day ends with the hiker hiking in the dark, a common occurrence on the trail. The hiker reflects on the day's challenges, including the hot and humid conditions, the persistent gnats, and the unexpected encounters with wildlife. The hiker also notes the importance of trail magic and the kindness of fellow hikers, which help to make the journey more enjoyable and memorable.

In my opinion, the hiker's experience on day 105 highlights the challenges and rewards of hiking the trail. The hot and humid conditions, combined with the presence of gnats and other bugs, make for a difficult day, but the hiker's determination and resilience shine through. The unexpected encounters with wildlife, such as the black bear, add an element of excitement and adventure to the journey. The hiker's appreciation for trail magic and the kindness of fellow hikers is a testament to the sense of community and camaraderie that exists on the trail. Overall, the hiker's experience on day 105 is a reminder of the importance of perseverance, adaptability, and a positive attitude when facing the challenges of the trail.

Day 105 – Great Barrington HERO (2026)
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