Hickey and Squaw Loop

MODERATE 162 reviews

Hickey and Squaw Loop is a 2.8 mile lightly trafficked loop trail located near Stockbridge, Massachusetts that features beautiful wild flowers and is rated as moderate. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

DISTANCE
2.8 miles
ELEVATION GAIN
685 feet
ROUTE TYPE
Loop

dogs on leash

kid friendly

birding

camping

cross country skiing

hiking

nature trips

snowshoeing

trail running

walking

forest

views

wild flowers

wildlife

rocky

scramble

hiking
2 months ago

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.

hiking
2 months ago

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.

3 months ago

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.

hiking
4 months ago

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

trail running
4 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.

5 months ago

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

hiking
5 months ago

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.

hiking
6 months ago

Nice but traffic noise.

hiking
6 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!

7 months ago

Hiked this today on a warm fall day! Great foliage

7 months ago

Gorgeous views and a very easy ascent on the Indian Monument Trail to the left after you park. Ran into a few people but they were all very nice. Even met a hiking couple from Colorado. Good news, Atlas (German shepherd) did not go after any chipmunks! ;) Though there were tons! I posted photos. It gets a little tight at the top and Atlas didn't want to go over the rocks, but then we saw that there was a pass around. All in all 5 stars! Would go again in a heartbeat. Oh. Bring your debit card. There's a meter for paying for parking at the lot.

hiking
8 months ago

Not super difficult, but I broke a pretty good sweat on the way up on an unseasonably-warm Fall day. The trail follows the road for a bit, so there's a good bit of noise, but eventually it meanders through the woods, climbing steadily until opening up to some pretty great views at the top. The trail was a bit rocky, interspersed with tree roots, but that's to be expected in this area.

hiking
8 months ago

Beautiful views at the top with well marked trails. One of my favorite hikes!

8 months ago

We two 70+year-olds really enjoyed this trail. The difficulty was in the rocky terrain and not the elevation, so it was fun but not taxing.
The trailhead is NOT at Fountain Pond Park, as stated in this app. It has its own parking area at 551 Stockbridge Rd. in Great Barrington.

8 months ago

Spectacular views from the exposed granite on the top in 360 degrees. Mostly anyone can do this hike. Good in all seasons.

hiking
8 months ago

There are three principal trails at this site which can make a loop or can be done as in and out trails. HIckey trail is steeper and takes you to Summit Trail which goes to the summit with lovely views and takes you down by a gentler grade trail. Moderate level, and the trail is in good condition. The summit is a bit rocky and "ledge-y" in spots.

9 months ago

Easy hike, great view! Very well marked trails and very easy to find.

hiking
9 months ago

Good hike with a nice view at the top.

hiking
9 months ago

Good times!

hiking
9 months ago

Great hike! Trail is very well maintained - some light rock scrambling is required near the peak. If you want a steeper ascent start north of the parking lot, more gradual go south.

hiking
9 months ago

Favorite trail in the Berkshires! I always do it at least once a year. Love the views and watching the birds circle below me on top of Devil's Pulpit.

walking
9 months ago

Def the monument trail to go up & the hickey trail to return

walking
9 months ago

Def the monument trail to go up & the hickey trail to return

hiking
9 months ago

Have hiked the trail many times although not one of the local experts. As long as it's not too hot or not a particularly buggy summer, it's a great hike. A few options such as a steeper shorter route up if you choose to start to the left. We usually go left but choose the longer more gradual incline. Definitely a moderate hike. Pretty steep with large rocks at/near the top. Great view from up top as you see in the photos. We love the Hickey trail for the descent. Really beautiful walk. Saw someone hiking the trail barefoot. Impressive! Last year we took our puppy along. We all had a blast. You pay a fee at the trailhead. There's a discount membership too.

Not lightly used in summer. Definitely moderate use. Bring water of course.

Enjoy!

9 months ago

Beautiful hike. Good views on the Red trail. It is a little rocky so wear good shoes / boots

10 months ago

Great Hike. Nice mix of terrain!!

10 months ago

Nice little up and down, fantastic views with some rocks to sit on at the peak. Travel a bit further south and visit Campbell Falls to make a nice trip

10 months ago

This hike is perfect. Nice distance, easily doable in 1.5 hours if you are in good shape. I would scatter my ashes from the top, the view is so magnificent.

hiking
10 months ago

Beautiful place, great hike, amazing views. Definitely more of a moderately trafficked trail in my opinion.

11 months ago

It's pay to park now but worth it. For me this hike is more "Easy" than "Moderate" so if you are a very experienced hiker this won't provide much challenge. Beautiful views at the top.

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