Cheshire Harbor Trail to Mount Greylock

HARD 64 reviews

Cheshire Harbor Trail to Mount Greylock is a 6.2 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.

6.2 miles
1922 feet
Out & Back

dogs on leash



nature trips

trail running




wild flowers




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

1 month ago

First week of May, pretty wet in spots. I thought it was a great hike. Views at the top were nice. We got to the pond and there were well over a hundred frogs there, quite something to see. The beginning is a bit lacking in views but the last stretch is fantastic between the pond, the forest (with snow in some areas still) at the top, and the view itself. Unfortunately the lodge and tower were closed, not sure if that is just because it is early or not. Overall a moderate hike that left me tired and took about 3.5 hrs.

2 months ago

I’ve been hiking this trail since I was a kid growing up in the area. I would call it moderate, not hard. Great summit hike for all ages and abilities. An average hiker will take 1.5 to 2 hrs to get to the summit, with breaks. There’s a good break spot about 2/3 of the way up at a bridge, just before you get to the AT. The last bit before the summit on the AT is the toughest, but very manageable. You’ll also see an AT shelter set next to a cute pond in this section, great picture spot. Summit views are well worth it and a great spot for lunch before heading back down. Overall, a good trail for a walk in the woods and the easiest way to achieve this summit.

6 months ago

Got so bored that I turned around, but that's just me. I agree with the other reviews here, and if you're an enthusiastic, nature-loving adventurer like me, pick a different route.

8 months ago

Pleasant walk in the woods. Should be rated as moderate rather than hard-- nothing technical, just a continuous ascent. The rise is continuous but not particularly steep. Summit was in the clouds when I went-- no views. Completed up and back in 2.5 hours.

8 months ago

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

10 months 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.

10 months 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.

10 months 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.

10 months 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!

11 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.

11 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.

Tuesday, May 30, 2017

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 !

Sunday, May 07, 2017

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

Saturday, April 15, 2017

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

Monday, February 06, 2017

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

Monday, November 07, 2016

great trail, amazing view

Saturday, October 29, 2016

This hike I found to be rather fulfilling. Not in the traditional sense with 1 great view at the top, but more so everything encompassed together as a whole.
The trail is very easy to follow and pretty straightforward winding a bit through the woods. It was raining and snowy when I went which made the walk a bit easier actually but slowed me down a bit. (Easier but slower steps).
With about 3/4 of a mile remaining the trail crosses the road and dips into some thick woods. There's a nice little lake with a cabin that you walk around before you reach the road again and a bit further to the summit. Very peaceful area and during the summer the lodge is open where in my opinion would be a great place to unwind and grab a bite before you go back down. The view is very nice but it can be windy up top.
Because the trail isn't too rocky and is a steady incline up and decline down, it won't take particularly long to finish. I would rate this as a moderate hike as no point is really that steep or challenging. The best part is the last mile.

Tuesday, June 14, 2016

We did this trail in late April 2016. Our first hike for the year. It was an easy one to start off the season with. Quite a few people at the top but very quiet pleasant views. The restaurant was not open yet at the top so no concerns of large amounts of people. Well maintained trails. This took us about 5/6 hours to complete.

Saturday, June 11, 2016

Great trail. One of my favorites on Mt. Greylock. Trail is usually well maintained and with the exception of Columbus Day weekend, not heavily populated.

Sunday, October 18, 2015

Great hike up Mt Greylock. Fairly easy hike. Some steep parts but not too strenuous.

Sunday, October 18, 2015

This was an excellent trail. Hiked it on the coldest weekend of October and it was snowing at the summit. Caught the lodge on its last day open for the season. Loved the AT and can't wait to go back to do more of the trails up Greylock.

trail running
Saturday, August 15, 2015

This is a favorite of mine to run to the summit of Mt Greylock. Sections are strenuous at times. There is a picturesque pond near the top. I love the WWII monument at the summit. And the views are great.

Tuesday, July 28, 2015

Great trail to the summit of Mt. Greylock. ook about 2 hours & 30minutes. Finally found a trail that brings you to the summit of Mt. Greylock. Very wide trail& easy enough as the grade is gradual. A must do!

Thursday, June 18, 2015

Great trail to use for your first hike up Greylock...can be pretty it was today. 6/18/15

Tuesday, April 21, 2015

Been eager to ascend Mt. Greylock for quite some time and as a newbie in the hiking world, I went in a bit anxious. Trail was pretty challenging (again I'm new) but it was a lot of fun. About 1/2 to 1 foot of snow in certain parts towards the top and that slowed us up a good amount. Views at the top were 100% worth the trek however. A few groupings of people throughout the day were seen and I can only imagine this place swells with numbers once the auto road opens up. TIP: Composting toilets at the summit (Over the weekend anyways) do not have TP, so plan accordingly. Will be back!

Monday, September 01, 2014

The view at the top is definitely worth the challenging hike up! We were doing the ascent for time and got there in 70 minutes but our heart rates were elevated the entire time. I can't wait to go back in the fall.

Monday, October 14, 2013

I survived the Mt. Greylock Nature Ramble. The hiking conditions were muddy, slippery, and rocky. The flow of hikers' was heavy. What a GREAT time!! I was sooo inspired to see a 93 year old accomplishing this hike. Stick with it because it's worth the hike :)

Monday, July 08, 2013

Picked a bad day to decide to reconquer this trail to the summit. The trail conditions were fine. Very light traffic. Very few hikers. The air temps were in the 90s and the humidity was extremely high which made the air thick and the climb difficult. The trail was easier than I had remembered. Forested on the way up with varying degrees of difficulty due to steepness of trail. Terrain obstacles included roots and rocks. The Appalachian Trail North section remains my favorite part. A bit more challenging than the rest of the trail and rated by most sites as strenuous but by that point, you're so ready to reach the summit, the distance flies by. There is a pond surrounded by tall pines and an AT shelter at the banks. Worth the hike. I would recommend returning via Gould though to West Mountain Road. Be careful if you return via Gould to watch for signs pointing toward West Mountain Road Parking area. Also if you return this way, keep in mind that the parking area is about mile down West Mountain Road than the entrance to Cheshire Harbor Trail's parking area.

Tuesday, September 04, 2012

Awesome hike. Views from the summit were great. Barely anyone on the trails but the summit was packed (most people drove up the access road). The tower was cool with expanded views of the different ranges. Definitely suggest this hike.

Sunday, August 26, 2012

Decided to hike this one today. My husband and I have only been hiking consistently for about a month on the weekends. The overall, 2 hours to the top and about the same down, but that's because we took the long way across Gould's Trail.
The first mile of the CHT was on the easy end of moderate. It became progressively more difficult the longer the trail went, increasing in grade and obstacles (roots and rocks). At some points there were rocks and roots that were probably about 2' off the ground that you had to step up onto. Once you cross the road and start following the Appalachian Trail North, the trail changes a bit. At first, you start thinking it won't be too bad, more of those same moderate conditions of rocks and roots. You pass over a bunch of board bridges, past a pretty pond with a structure at one end. Past that it starts getting strenuous. It is steep, narrow in points, and definitely will get your heart rate up. The summit is okay. I think the views are better on Talcott and Sleeping Beauty. It is very tourist-y at the top with plenty of people who drove up instead of hiked, but still plenty of hikers, mountain bikers, road bikers, etc.
The food at the lodge was pretty good. There's a small gift shop and rest rooms.
The way down you follow AT South, then according to the "suggested hikes" from the Greylock site, you follow Gould's Trail down. Gould's is narrow but not bad in intensity. We branched off to the Pecks Brook Shelter Trail, thinking it was the one we supposed to take. There's a shelter for camping and a rock fire pit. Off to the right of that was a waterfall. We doubled back onto the Gould's trail and then followed down and found the Peck's Brook Loop by finding a half broken Cheshire Trail direction sign leaning on a downed tree. That trail was tough. Narrow. Eroded in spots. Go down into a ravine and then a very steep climb on a very narrow path back up quite a distance 'til you get to the CHT. Of course then, the rest of the way isn't bad at all because you've along got a little over a mile left of the CHT.
Overall, I think we spent 6 hours on the trail, but we rested a while at the top and probably about a half hour at the shelter. We were also slow on the way down because I got sick.

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