Hickey and Squaw Loop [CLOSED]

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Monument Mountain Reservation

Hickey and Squaw Loop [CLOSED] is a 2.8 mile heavily 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

camping

cross country skiing

hiking

nature trips

snowshoeing

bird watching

running

forest

views

wild flowers

wildlife

rocky

scramble

closed

As of May 2020, users have reported this trail still has a temporary closure due to COVID-19. Please see the park's website for up to date information.

hiking
8 days ago

Outstanding, 360 degree views for relatively little effort.

14 days ago

closed

hiking
snow
1 month ago

This is my go to training mountain. Hike it 2 times a month and a good work out going up the steep hickey trail. Like the view of greylock on a clear day. I do this in addition to other training. Frequent Taft farms after the climb. I do his year round and love the snow hikes when available. Have fun!

hiking
2 months ago

My favorite trail of all time. Beautiful views- make sure to climb the stone steps to devils pulpit overlook. That is my favorite view. The only downside is that it’s a top hiking spot and can be swamped with people during the summer and weekends.

hiking
2 months ago

Do well maintained! Beautiful.

hiking
icy
3 months ago

hiking
scramble
6 months ago

hiking
6 months ago

Great hike at a relaxed pace, took about 75 minutes! Lost the trail a couple times, but that led to a great lookout. Definitely recommend.

hiking
6 months ago

Great views!!

hiking
6 months ago

Hard to see the trail with all the fallen leaves, but overall beautiful with a few nice viewpoints.

hiking
7 months ago

Excellent hike. Just the right amount of challenging parts to keep it interesting but doable. Perfect way to enjoy fall foliage.

hiking
7 months ago

This was the perfect hike! Rewarding, a little challenging, and quick! My boyfriend and I did this in about an hour and a half. It was busy/crowded at the top, but the trail didn’t feel packed at all during the climb/descent.

hiking
rocky
7 months ago

Was a nice trail. Get there early, parking in the lot gets tough, there were so many cars, about 40, people had to park in the grass doubled up. I would definitely say this is a heavily trafficked trail. We saw easily 30-40 other groups of hikers, continually had to move over to allow large groups to safely pass in some parts. The trail was groomed nicely however sometimes hard to follow on the Squaw trail (red markers). We did get a tiny bit lost once following the red markers but we quickly figured it out. I will say, don’t start with the Hickey Trail unless you want a steady incline for about 0.8 miles. We started with the Monument Trail (blue blazes) to the Squaw trail (red blazes) then to the Hickey Trail (yellow blazes). Saw some people having a tough time getting up the Hickey trail. I also say start with the monument trail because it follows the road for about 0.5 miles and would have hated to end a hike with all the noise from the road. We didn’t realize until we were done hiking that there is a pay station where you have to pay $5 to park. There were so many cars, it blocked the one and only small sign that says it’s $5. We paid before we left because we felt bad we didn’t pay up front. Hike took an hour and fifty minutes. TONS of dogs, 1 in every 5 dogs were off a leash which doesn’t bother me but just a warning if pups make you nervous near cliff edges. I would do this hike again, views were ok.

hiking
rocky
scramble
8 months ago

What a nice hike. We definitely started off on the Hickey Trail to Squaw Peak Trail and ended on Indian Monument Trail. It was better to get the harder trail over with. Definitely would not have liked coming down Hickey Trail as it steep and rocky in most areas. The trails have been kept up well. Definitely take Squaw Peak to get the views. Definitely would recommend this Trail.

hiking
rocky
scramble
8 months ago

Great afternoon hike with awesome views in 2 directions from the top. We hiked with kids and our dog and everyone enjoyed. We went to the right from the parking lot and had the steeper rockier ascent, and the longer mellower trip down. Nice loop trail.

hiking
8 months ago

Great trail options for all levels of outdoor enthusiasts! Stunning views if you can make it to the top, and even the “toughest” trails are a breeze for the athletic type.

hiking
8 months ago

Beautiful spot on top

hiking
8 months ago

From the parking lot, we chose to start to the right, which is a moderate steep climb. At the inscription rock, we connected to Squaw trail which has a good photo opp on the boulders. From there, it was hard to tell where the trail continued so some people turned back, but we kept on, and it was a very easy (though long) descent. 2 hours total. Mostly wooded, so hard to see the views except for that one spot at the top.

hiking
9 months ago

This has to be maybe my new favorite trail. It's easy, quick, clear, and fun with an amazing vista at the top with some cool places to explore and scramble if that's what you want. I could spend all day at the top with a book and a sandwich. It's gorgeous. Makes up for the end of the trail that runs parallel to the road; it's quite noisy there. We went clockwise but maybe I would try counter clockwise so that the noisy path isn't the last thing I remember.

hiking
9 months ago

We traveled up the Indian Monument trail, then up Squaw Peak and down Hickey. All of the trails are very well marked and maintained. There's a lot of foot traffic, but plenty of room to step aside or even share the trail with passers by.

hiking
9 months ago

I’d recommend this trail for anyone looking to get outside in nature, solo or with a small group and their dog(s). Watch out for dog poop on the trail. Vigorous and a good way to get your heart beat up. The views are definitely worth it, albeit smoggy today.

hiking
9 months ago

Nice little hike with a good view! Very much worth the parking fee because the trail is so clean and well maintained.

hiking
bugs
9 months ago

hiking
bugs
9 months ago

hiking
rocky
10 months ago

when we got to the split for Squaws Peak, we took it. It's a bit rocky and steep.at points but when you get to the top, you know why you did it. The views are amazing. Take a minute to catch your breath and enjoy this for a while. there are several points to look out and they are equally beautiful. Take the high road and check Squaws Peak out. It's well worth it.

hiking
10 months ago

one of my favorite peak baggers!

hiking
11 months ago

Good early AM warm up with my wife. Tracked 2.6 mi about 1:30hrs. Was raining but decent cover on trail, although some slippery spots.

hiking
Mon May 27 2019

Gorgeous views and if you take the Squaw Loop up it’s a bit steep but if you take the Hickey Loop up, it’s a little easier. Maps available at the trailhead.

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