Explore Berkshires - view hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

Berkshires Map

This hike is very popular, and for good reason. The Hickey Trail leads to the summit at a moderately steep grade. The Squaw Peak Trail then traverses the ridge, where there are great views of the Berkshires. Descend via the Indian Monument Trail, which is longer and more gradual than the Hickey Trail. My only criticisms are that despite its popularity, there are no restrooms at the bottom, and there are some large cliffs at the top.

I did this hike with my ten year old son. He is starting to enjoy hiking and so this was a perfect one for him. We took the Hickey trail which was a bit steep, made a few stops for him to catch his breath. Along this path, you will come to a nice small waterfall and stream. Right before hitting the summit, there was a cool little ledge with a nice view. Once you reach the peak, there is a 360 view. My son loved it. We then followed the Squawk peak train, into the Indian Monument trail back. This trail was pretty flat, that followed the along the main road. The entire hike took two hours, maybe slightly more. Nice... would recommend.

Hiked solo. Perfect day, still ice on trail for last mile needed crampons

23 days ago

The first half is all up hill, more than I anticipated. At the summit you can’t see anything, unless you climb up the fire tower. I was expecting some sort of clearing at the top. The overall hike was very muddy and slippery. Decent and well marked, but wouldn’t do it again.

I took Bellows Pipe from Gould Rd. tried to hike up Thunderbolt but found it to be to difficult to get footings due to ice. I continued to take Bellows Pipe up to the summit, still very slippery but doable.. Great trip!

Always a nice hike although today it was quite muddy. But who can complain about a 70 degree day in February. A little ice but it and the mud was fairly easy to get around.

A lot of overlap with the snowmobile route so watch out. Even after a few inches of new snow, still dangerously icy underneath.

This hike was stunning, I hiked it a few weeks ago when there was at least 1/2 foot on the trail and gradually got thicker while climbing. Icy and cold, but I embraced it, because a "silent tundra " is waiting at the top for you, that is overwhelmingly beautiful. I Want to hike it again before spring!!

Great hike. Took the Thunderbolt Ski trail up and the bellows down. There are a couple of trees on the trail - nothing you can't scramble over. And don't leave your snowshoes in the car like I did, once you approach the summit, they will come handy. There was fresh powder, so it was a lotta fun. Beautiful weather too.

Great day hike to the highest peak in Massachusetts. Wonderful views at the top.

on Bash Bish Falls Trail

1 month ago

If your in western Massachusetts or eastern N.Y. traveling on 87, this is worth a stop. Short hike down to some dramatic falls . Don’t forget your camera!

2 months ago

Fantastic Hike! Gold trail - great challenge. Beautiful views.

trail running
2 months ago

A good loop and challenging although the trails were very icy so I wasn’t able to make it all the way around and had to turn back. Look forward to going again in the spring.

dope as sh^t

3 months ago

Started from the parking lot at the Mass Audubon Pleasant Valley Sanctuary. Stayed to the left around Pike's Pond (lots of beaver activity around here) until I connected with the Ledges Trail. A few steep ascents and scrambles, which can get a little slick and dicey... Make sure you've got decent footwear! From the top of the steepest ascent, you walk through a lovely alpine-like area with a low canopy and several nice viewpoints. Reaching the cell tower at the summit, there's a great view, but it was very windy so we quickly headed back down along the Overbrook Trail. Great, lush, scenic walk through the woods - and perfectly well-marked the whole way.

The steep, short side is the best! Definitely a beautiful Berkshire favorite!

Two words: stunning view! ...but boring gravel road. If you like running on a gravel roads and magnificent views, this is for you :)

went at 9am, only a few other people, quick hike. Gradual incline. Indian trail runs by the road, which is a luttle distracting, but the peak is great! Definitely recommend stopping at Devil's Pulpit for the best views.

3 months ago

Great trail! Is definitely moderate and very well marked. Our dogs loved it too and it took us about two hrs. We started kind of late and ended up coming out in the dark, but the trail was easy to follow once we couldn’t see markers anymore. Very pretty, windy, and we even found some chagga.

Great view atop the mountain. I️ would consider this a challenging hike, becoming more challenging towards the top. Perfect November day.

Beautiful fall day in esrly Nov. Trails were well maintained, however trails maps at the mountain I found to be confusing. An excellent hike overall.

Very steep in spots. Definitely a trail for younger legs.

Short hike with awesome views of a moderate waterfall. All along the trail, the air is filled with the sounds of running water, as the path parallels the stream.

Nice but traffic noise.

4 months ago

Beautiful mountains with captivating views. Though it gets steep at certain points, the trek to Devil’s Pulpit is well worth the adventure!

Nice easy hike, but definitely not an lazy stroll thru the woods. Some muddy patches. Interesting signage about the history of the tower. Awesome views!

4 months ago

Short, rugged trail, boulders and tree roots, natural stone stairs and long wooden steps. Stones down around the falls are smooth and slick from years of traffic, you just have to be careful. Not many visitors this time of year and cooler temperatures made this a very pleasant and quick hike. Very pretty hike through mature forest with lots of moss covered boulders.

Hiked this today on a warm fall day! Great foliage

What a hike! I accidentally got off trail (not entirely atypical for me) and ended up doing a straight vertical incline UP a ski racing trail. Plus side? I bumped into a ski group clearing the trail for their race in February and they shared a delish craft beer with me. Downside? I was practically climbing up a mountain with a full beer in me ;). Slow and steady wins the race, I say. Weather was perfect (warm for the fall), amazing views, and overall excellent hike. P.S. - went down the right trail on the way down...what a difference!

Moderate/easy hike on the AT! Most sections of the hike are flat. I really loved the spot at Rand’s View- definitely has to be one of the best viewpoints on the CT AT (it’s featured at the REI in Milford likely for that reason). Would definitely recommend!

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