Hiking Mount Greylock to Vermont: 1600 Miles and Counting! (2026)

Today, I want to take you on a journey through the experiences and reflections of a hiker on their 108th day of an epic adventure. This is a story of perseverance, unexpected pleasures, and the beauty of nature's challenges.

The Daily Grind

The struggle to get going in the morning is a familiar battle for many, especially when faced with the physical demands of hiking. The heat and humidity add an extra layer of difficulty, sapping energy and motivation. It's a testament to the hiker's determination that they continue pushing forward, day after day.

Scaling Mount Greylock

Mount Greylock, the tallest peak in Massachusetts, presented a gradual yet rewarding climb. The ascent, though long, offered opportunities to catch one's breath and admire the surroundings. Reaching the summit, the hiker was greeted by a lodge, a welcome respite with its cold beverages and a much-needed bathroom break. The monument at the top provided a unique perspective and some inspiring quotes to reflect upon.

Descending with Determination

The descent from Mount Greylock was a mix of steep sections and more manageable terrain. Despite the heat, the hiker persevered, occasionally pausing to take in the views. It's a testament to the power of human endurance and the mind's ability to push through physical discomfort.

Trail Magic and Tired Travelers

Arriving in the city of Greylock, the hiker and their companions were met with a pleasant surprise - trail magic! Coolers filled with snacks, water, and cold drinks provided a much-needed boost of energy and morale. This act of kindness from strangers is a beautiful aspect of the hiking community, offering support and encouragement to weary travelers.

Crossing State Lines

As the hikers ventured into Vermont, they passed the 1600-mile mark, a significant milestone in their journey. The transition from Massachusetts to Vermont marked not only a new state but also the beginning of the Long Trail, a renowned hiking route. It's a reminder of the diverse landscapes and experiences that await on the trail.

Border Crossing and Bonus Miles

Reaching the Vermont border sign, the hikers celebrated the completion of their 11th state and the start of a new adventure in their 12th. However, a small setback occurred when one of the hikers realized their earbuds were missing, adding an unexpected 0.6 miles to their journey. It's a reminder that even the most well-planned adventures can have unexpected twists.

A Warm Welcome and Parting Ways

The day's hike concluded with a warm welcome from Becca, who greeted the hikers with cold beers and fast food. It was here that one of the hikers, Birdie, parted ways with the group, each with their own Fourth of July plans. The remaining hikers, Shooter and the narrator, headed to Bennington with Becca, looking forward to a well-deserved rest at the Catamount Inn.

Technical Difficulties and Thunderstorms

As they made their way to the inn, the hikers encountered technical difficulties with a phone screen malfunction. Despite the annoyance, the phone remained usable. The journey was further challenged by thunderstorms, with lightning flashing all around. It's a reminder of the unpredictable nature of outdoor adventures and the need to remain adaptable.

Day 108 Recap

In summary, Day 108 was a day of contrasts - the struggle to get going, the rewarding climb of Mount Greylock, the kindness of strangers on the trail, and the excitement of crossing state lines. It's a day that showcases the physical and mental challenges of long-distance hiking, as well as the beauty and support found along the way.

Final Thoughts

Hiking is a journey of self-discovery and resilience. It's a testament to the human spirit's ability to overcome challenges and find joy in the simplest of pleasures. Each day on the trail presents a new adventure, a new lesson, and a deeper connection with nature. So, let's continue to embrace the journey, one step at a time.

Hiking Mount Greylock to Vermont: 1600 Miles and Counting! (2026)
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