One of the many fun things about hiking is simply just finding the trail head. All the back roads and routes that you need to take to find the trail head is a fun part of the adventure. This was true of this hike. I always get lost when trying to find the trail head since I try to look at google maps and try to remember how to get there. A cool part of the trip up to the trail head is that you are able to see the top of the mountain from the road.
Looking at the top of Mount Greylock from the road.
Nevertheless I found the Cheshire Harbor Trail head and the hike was on. There was only one car at the trail head. It was a Friday.
The hike starts up this old fire road which was really quite wide. The grade is gentle is the trail is very easy to follow. At this time in April at times the trail was quite wet. At some points there was considerable amount of water running down the trail. I would definitely recommend wearing waterproof boots since the trail was very muddy down low. You will follow the trail up until you cross the road where you will pick up the Appalachian Trail and you will follow the trail to the top. At this point the trail was quite icy.
Summit is close
You will pass a small trail with a shack next to a pond. At that point you are very close to the top. The Veterans War Memorial will come into view and that is the top. Return in the same direction.
The view looking east towards Adams