Cheshire Harbor Trail to Mount Greylock

HARD 72 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
1,922 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.

29 days ago

nice easy hike, do it semi-often. Did it alone in an hour and 45 up recently. halfway down heard what I can only describe as two monkeys calling to each other...

1 month ago

Hiked this trail many times during my childhood and it was the perfect challenge for my 11-year-old daughter and me to hike together. On a clear summer day, the views are amazing. The lodge has a great menu too.

1 month ago

Steady but moderate incline trail with a few steeper sections. Rocky, but well maintained. Worth the views and the trip up the war memorial tower at the summit.

3 months 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.

4 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.

8 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.

10 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.

10 months ago

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

Saturday, August 12, 2017

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.

Tuesday, August 08, 2017

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.

Monday, August 07, 2017

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.

Sunday, July 30, 2017

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!

Sunday, July 09, 2017

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.

Wednesday, July 05, 2017

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 :)

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