Mount Greylock Summit via Cheshire Harbor Trail and the Appalachian Trail

Six Pack of Peaks: New England – Mount Greylock

I started  hiking from Chester Harbor Trailhead Parking was attempting to catch a sunset at the summit. From Cheshire Harbor Trail I connected with the Appalachian Trail then to the summit. Weather was a bit overcast and in the distance clouds looked like it had breaks and maybe a chance for a sunset. Most of the trail is below tree line but there were some views more near the summit. At the summit you don’t get 360 views unless you can get access to the Massachusetts Veterans War Memorial Tower. Though it was overcast had I had views of the valley, towns below, views of close and some distant mountains. Clouds continued to roll in and wasn’t able to get the sunset but there’s always another time. There were not many hikers but a couple that biked the road up to the summit. Spent a little bit at the summit exploring before heading back south on the Appalachian Trail and then connected back onto the Cheshire Harbor Trail. It was definitely a great hike with a gradual up to summit but was worth it. Greylock never disappoints.

Date: 5/15/2026

Start: 6:20pm

End: 9:05pm

Miles: 6.5 Miles

Cheshire Harbor Trail to Mount Greylock on AllTrails
https://www.alltrails.com/trail/us/massachusetts/cheshire-harbor-trail-to-mount-greylock?sh=qivyuv&utm_medium=trail_share&utm_source=alltrails_virality

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