Hiking Mount Greylock: A 1600-Mile Journey and Entering Vermont (2026)

On day 108 of my journey, I found myself at Mount Greylock, a towering peak in Massachusetts, marking 1600 miles into my adventure. The morning struggle, a familiar foe, was particularly challenging due to the recent heat and humidity. But, with a decent breakfast fueling me, I embarked on the ascent, determined to conquer the mountain.

The climb up Mount Greylock was a gradual challenge, offering leveled-out spots to catch my breath. After almost 3000 feet of elevation gain, I reached the summit, greeted by a lodge and a breathtaking monument. The monument, adorned with inspiring quotes, provided a moment of reflection and a chance to recharge with a cold beverage.

The descent was a test of endurance, with the heat and humidity sapping my energy. Yet, I pushed through, knocking out the miles with a sense of determination. The trail magic in Greylock, with coolers full of snacks and water, was a pleasant surprise, offering much-needed sustenance and a chance to socialize.

As I ventured into Vermont, the 1600-mile mark was a significant milestone. The climb to the Vermont border was a test of my endurance, and I was relieved to catch up with Shooter, my hiking companion. However, a minor setback occurred when I realized my ear buds were missing, forcing me to backtrack and adding an extra 0.6 miles to my day.

Despite the challenges, I persevered, and the warm welcome from Becca at the road was a much-needed boost. We shared a meal and a cold beer, and I said goodbye to Birdie, as our paths diverged for the 4th of July. I headed to Bennington with Shooter, looking forward to a night's rest at the Catamount Inn.

This day was a testament to the resilience and determination required in long-distance hiking. The struggles, the surprises, and the camaraderie all played a part in shaping my journey. As I reflect on this day, I realize that the challenges faced on the trail are not just physical but also mental and emotional. It is a constant battle against the elements, fatigue, and self-doubt, and it is these struggles that make the triumphs all the more meaningful.

Hiking Mount Greylock: A 1600-Mile Journey and Entering Vermont (2026)
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