Hiking Mount Greylock to Vermont - 1600 Miles of Adventure (2026)

Day 108: A Journey Continues

The morning struggles persist, but today's adventure begins with a hearty breakfast at a decent hotel. We hit the trail later than planned, around 9 am, and embark on a challenging climb up Mount Greylock, Massachusetts' tallest peak. The ascent is manageable, offering a gradual path with resting spots, and I finally reach the summit after a 3000-foot elevation gain over 7+ miles.

The top reveals a lodge with refreshments and a monument with inspiring quotes. Descending, the heat and humidity take their toll, but I power through, reaching the bottom in Greylock. A pleasant surprise awaits as we encounter trail magic—a treasure trove of snacks, water, and cold drinks.

As we bid farewell to Massachusetts and enter Vermont, the 1600-mile mark is celebrated. The trail continues with a steep climb, and I reunite with Shooter at the Vermont border. A minor setback occurs when I lose my ear buds, adding stress and miles to the day, but I eventually reach the road, where Becca greets us with fast food and cold beers.

We bid farewell to Birdie, heading to Bennington with Becca. The Catamount Inn awaits, but a phone screen issue adds to the day's challenges. Despite the setbacks, the journey continues, and I reflect on the day's struggles and triumphs, grateful for the support of fellow hikers and the beauty of nature.

Day 108 Stats:
- 21 miles
- 5,751' ascent, 4,432' descent
- MA Route 8 to Catamount Inn via County Road
- 0 DSLC
- Stove used 14 times

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Hiking Mount Greylock to Vermont - 1600 Miles of Adventure (2026)
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