Cheshire Harbor Trail to Mount Greylock

HARD 47 reviews

Cheshire Harbor Trail to Mount Greylock is a 6.3 mile moderately trafficked out and back trail located near Adams, Massachusetts that features beautiful wild flowers and is rated as difficult. The trail offers a number of activity options and is best used from March until October. Dogs are also able to use this trail but must be kept on leash.

DISTANCE
6.3 miles
ELEVATION GAIN
1942 feet
ROUTE TYPE
Out & Back

dogs on leash

birding

hiking

nature trips

trail running

walking

views

wild flowers

wildlife

The easiest and shortest ascent route from base to summit of Mount Greylock, the highest peak in Massechusetts. Spectacular views at summit.

hiking
3 days ago

The trail is not very steep, but it's not very scenic. Great views at the summit!

hiking
1 month ago

Hiked this trail at the beginning of April of this year, when there was still snow on the ground. It was a pretty wide trail and well maintained. Good intro to winter hiking. Towards the summit, it merges with the Appalachian Trail for a short bit, and that part of the trail was quite woodsy, but still easy to get through with the snow. Did this trail at a fast pace due to the cold and it took about 4 hours to get to summit and back down again. Did not need snow shoes, but the snow was on its way to melting and pretty packed. Might need them other months out of the year.

hiking
1 month ago

The trail itself was not very scenic but it was an enjoyable hike. Not very steep, good option for first timers. About 4/5 of the way up there is a beautiful little pond. The summit of Greylock is absolutely beautiful with views for 100 miles in every direction, 4 different states are visible from the top. This was worth every step.

hiking
1 month ago

Not much to see on the trail itself, at least until you get to the AT. This was my first time hiking up any mountain and I found it challenging but doable. View is fantastic, worth every step.

hiking
1 month ago

After reading the description and reviews here, we assumed this would take us (49 year old hikers not in top shape or weight) between 5 and 6 hours round trip, likely closer to 6. We are not tremendously fast hikers, but we aren't overly slow either. We tend to keep a steady pace.

The trail was not hard and was a steady even climb, although you had to watch your step for loose stones and roots (nothing terribly unusual). The final part of the trail where it joins the AT was gorgeous! A little steeper but again, not too bad.

We were at the top in 1:54. We had a bite to eat, wandered around and enjoyed the view (we loved the map showing the various locations of other mountains and towns), and checked out the lodge. We opted to take Gould Trail part of the way down for a change of scenery. This trail was interesting and peaceful. We were down in a total of 1:46, for a total hike time of about 3 hours 40 minutes.

We felt that the trail was not "hard" or "difficult" at all... We had recently hiked up Monadnock on Pumpelly Trail, that to us is hard. This was straightforward and simple. You do get tired, you're going up a mountain, but it was a great trail that anyone who hikes can do. Very enjoyable!

hiking
2 months ago

hiking
2 months ago

Inexperienced hiker but athletic. I found this moderate but not entirely difficult. My travels up, around the summit, and down totaled 6.9mis and I accomplished this in roughly 5hrs. A wooded hike with little view until about 2/3 of the way when you cross the street for the first time, the flora changes with the elevation and it gets a bit more interesting. Areas of the trail are slightly wet but easily passable. Great view from the summit. I hiked this on a July weekend and the trail itself was not crowded but the summit was packed, cars were lined up waiting for parking spots.

hiking
2 months ago

The summit of Mount Greylock was spectacular! This route was straightforward and moderately strenuous but didn't have many views until the top. On the way down we took the Gould trail (we think) instead and enjoyed hiking along the river a lot more. This hike took us about 5 hours including a few breaks and plenty of time at the summit.

hiking
2 months ago

2 months ago

hiking
2 months ago

I chose this trail because it was described as the easiest way to the summit and I didn't want to bite off more than I could chew having not done a summit hike in some time. The first ~3 miles, the Cheshire Harbor trail, steadily ascends through the woods on a wide and easy to follow trail. The most rewarding and interesting part however was the .75 stretch of the AT that brings you to the summit once you cross the road at the end of the Harbor trail. This stretch is short but beautiful and dense. It passes a neat little pond and the smell of the evergreens is strong in the air. I did this on a foggy day which added a "deep in the woods" feel. The summit was completely foggy and offered no views, but I drove up the summit road afterwards once the fog broke. If you ignore the town of North Adams directly at the base of the summit, there are nice rolling mountains in the distance and far visibility.

hiking
2 months ago

3 months ago

I did this hike during Winter. Weather was quite challenging. The wind chills at the summit was -25F. If you decide to do this hike in winter, I would definitely recommend you to carry warm clothes.
Beautiful views from the top !

3 months ago

4 months ago

4 months ago

great trail, but drainage isn't good. Wait for a period of dry weather.

4 months ago

hiking
4 months ago

hiking
5 months ago

Great hike on a beautiful April day! Some mud and snow pack, but overall in pretty good shape for this time.

hiking
7 months ago

Well blazed and lightly packed by snowmobiles although I only saw them in the Summit road.