Monument Mountain

This hike was super, I’d rate it «moderate.» The views at the top were gorgeous, although there’s some sketchy climbing-​over-​rocks at Squaw peak! It was really windy up at the summit on the day we went, but it’s a really glorious hike. I think this is a great introduction to hiking for a first-​timer.

The pay parking was the most disappointing part of this experience. I was there for a very quick power hike to squa peak and back with only an hour to spare. There are no hourly options for parking at the kiosk. Just a flat $ 5.00 fee «for the day». I’m all for supporting these trails and parking maintenance but there should be options. I noticed a couple was also put off by this paying kiosk fee and parked just a bit up the road where there is a pull off and they cut over to the trail from there.

A fine hike, mostly through shrouded woods, but opening up to an emotional payoff once you get to Squaw Peak. The hike is of moderate difficulty, with occasionally demanding passages that require some giant steps upward to get a toehold on level ground. Once you break through to the summit, the panoramas are very much 360 degrees, with multiple states coming into view, principally New York and Connecticut. Happily, the way down shares nothing in common with the way up. You might find yourself incredulous that you return to the same spot as the hike originated, as it feels as though you’re heading down and far away from the peak for the longest time. But at the end, there’s an abrupt about face, and, can it be?, soon your car has come into view somehow.

I did this hike on a holiday morning in early October with my husband and our two good-​sized mutts. If you plan on going to the summit (which I highly recommend), be aware that parts of this trail are pretty friggin’ steep. Additionally, there are narrow rocky passes near the top that were difficult to navigate with leashed dogs. That said, the views are absolutely amazing and well worth the climb. We hiked the easier trail until it joined with the summit trail and used the summit trail to bridge back to the other end of the easier trail. We planned for a two hour hike and just about hit that mark. Bring a camera, a bottle of water, and some trail mix — you’ll be good to go!

Let’s just put it all out there: I don’t hike, I’ve never hiked, I don’t know the first thing about hiking. So if I can do it, can’t be bad right? Right! Monument Mountain was a great intro to hiking 101!
Thank goodness for fellow Unilocalers who wrote about this spot, otherwise I don’t think we would’ve found out about it. We were in the area and wanted to enjoy the beautiful weather and these trails did not disappoint.
The ranger on duty that day was eager to help and walked up to pretty much anyone who approaches the map to make sure their well acquainted and equipped with a map and an environmentally friendly bug repellent.
There are 3 main trails 2 which lead you up and down the mountain. Hickey Trail is a bit of a steep ascent which gets you to Squawk Peak Trail relatively quickly so you can get to the breathtaking views! Luckily we started with Hickey which sets you up for a relatively smooth descent down Indian Monument Trail in your way back. We skipped over Devil’s Pulpit for time purposes but we enjoyed the panoramic views of the Berkshires along Squaw Peak Trail. We spent a total of an hr and change on the trail but you can definitely extend your route.
Keep in mind there is a $ 5 «parking» fee for the entire day unless you’re a member. Small price to pay for a well manicured and well marked trail.

Like a walk in the park– then you will love
Monument Mountain! Today was my 6^th ascent and I still love it as much as my
1^st.
Please note that there is now a 5 dollar fee to park, credit/​debit card only (like a muni meter only solar powered).
As always, I take the Hickey Trail up to the summit. Hickey is the shortest route but the steepest– my fitness regimen allowed me to climb non-​stop and just a little bit winded. The route takes you past a gorgeous rock cropping that I someday would like to scrabble up. Recent rain runoff provided interesting focal points of small waterfalls.
The summit at Squaw Peak allows for 360 degree panoramic views of the surrounding mountains to all sides. The large rocks provide seating for rest and reflection.
After a break, off to the Devil’s Pulpit, striking rock formation reached by climbing large rock stepping stones.
I looped back on the Indian Monument Trail to Inscription Rock and back down Hickey!
Trails are well marked, meticulously kept. I marveled at how pristine everything was, not a bit of trash or signs of human trespass, until near the descent someone left a coffee cup on a log –really!!!
BTW– dogs seem to love it as much as their
owners.

Good hike for all abilities! Monument Mountain is a great, short hike for all fitness levels right in the center of the Berkshires (just outside Great Barrington). There are 3 different trails and it was nice that you could start with a difficult trail and then choose a friendlier trail for your descent, or visa versa.
Monument Mountain is dog-​friendly and even the most difficult trail was dog-​friendly for the most part… there were some large rocks to jump/​climb so a tiny dog may have to be carried, but I don’t imagine small dogs do too much hiking.
It took us about 90 minutes to complete the hike. Good views from up top. We went early in the day on a Sunday which seemed to be a good way to avoid the crowds.

A group of friends and I did this hike while visiting the Berkshires and really enjoyed it! It is essentially a big loop with a «leisurely» route and «more strenuous» route. We spent 2.5 hours here and took our time to enjoy the nature and views and many breaks. The view at the top is nice but I really enjoyed just walking through the beautiful trees and being in the mountain air. The Devils pulpit is also a «place of attraction» on the hike which is a nice view of a pretty cool rock structure. We also enjoyed the view at Devils pulpit a little better than the view at the top. This was a very enjoyable hike and one of the highlights during our weekend here.

I hiked Monument mountain alone, and while I’m cautious of doing this with longer hikes, there wasn’t a moment on this hike that I felt scared for my safety.
The trails here are some of the most well maintained and marked trails I’ve ever seen. I like that there are 2 very different options for getting to the top — a short (less than 1 mile) steep ascent, and a gradual 2 mile trail. I decided to make a loop of the 2 by adding in the cross trail and went up the steep side and down the gradual side. It made for a perfect hike.
There’s very few mountain peaks where you can get a 360 degree view like you can at the top of Monument mountain. You can see Mt. Greylock an several other mountains on all sides.

The views at the top of the trail make this a five-​star review. That and the condition of the trails.
On a recent visit to the Great Barrington area, a group of us decided to hike Monument Mountain. We were told it was not an exceptionally long hike, but that the views were spectacular. That is true on all accounts!
We started by taking the Hickey Trail up the mountain, which is not very long but definitely gets the blood pumping. It was a nice sunny day and was not buggy which was a pleasant surprise. The trail starts to ascend rather quickly. Our group moved at a pretty healthy clip, so it was a decent workout and took about 30 minutes from base to summit. As you get to the top, you can walk along the range and find a rock to sit on and admire the views. On a clear day, you can see for miles and it is a lush green landscape. You can see Mt. Greylock from the summit, as well as Butternut. On a good day, hawks will be flying above.
We took the longer, more circuitous route down, called the Indian Monument trail. It is a much less steep trail and would be more suitable for beginner hikers, or someone who did not have appropriate footwear. If you’re taking the Hickey Trail, you don’t need serious hiking boots, but you do want sturdy shoes.
The Trustees of the Reservation maintain the trails, so be kind and leave a donation at the box adjacent to the parking lot.

just do it. it’ll be crowded throughout the fall but the mountain’s big enough for everyone. stop, hike, then go to windy hill farms for apple cider.

The blizzard of ’10 thwarted my plans to leave this country and spend some time recharging. Heartbroken and listless though I was, the need to exit stage left still pressed upon me and so I escaped the dirty-​white city and drove northwards towards the mountains.
The snow lay thin here, but the air was clear and peaceful and bright.
As I stumbled hesitantly on the trail, ill-​equipped and cold, I still was happier than I had been for a while — happy to not be around the hustle and bustle. Happy to be outside in the quiet winter afternoon, with the potential for bear-​sightings entertained in my mind.
Escape is only a few hours’ drive away.

Breathtaking views of Massachusetts! Great workout and a rough climb but once you reach the top of the mountain; it’s amazing. Though, I couldn’t work up the nerve to sit on a ledge of a rock (some people did with legs dangling over the edge) but comfortably sat on another a little safe distance for a long while. Great place to relax, ponder, inspire and take in the majestic wonders of it all.