Beautiful trails and an amazing view from the top. We arrived around 11AM on a fall Saturday and there were only a few spots left in the parking area. There is a $6 fee for parking, and the machine takes credit cards. We hiked up to the summit on the Blue trail which connected to the red trail. Trails were clearly marked and not too difficult. We even found a few geocaches along the way. Be sure to take the short spur trail to Devil's Pulpit for a spectacular view. Even though the parking lot was nearly full, there are enough trails to that we never felt crowded. It took us about 2 hours total for our climb up and down the mountain, with some time spent enjoying the view from the summit. read more

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Finally came here after having it bookmarked for years. Medium lot fills up quick. Paid parking. 9 bucks. There was a DCR worker there helping people figure out which trail was better for them. He was very polite. There are 2 trails to get to the top. You can take the steep shorter trail or a longer trail that wasn't as steep. I opted for the steep one. Definitely a good little hike. I was out of breath. The top has a phenomenal view. Absolutely breathtaking. Definitely a place you need to put on your list of things to do. read more

Great place to hike and enjoy the outdoors! You have your choice of 3 trails! Starting in the lot, facing the mountain, go to the right, the yellow trail. Yes it is the more difficult path, but its the shortest way to the top. It is great if you're looking for a challenge or a workout. It is great if you want to see nature, including the many playful chipmunks, at its finest! We took the Red, into the blue trail down. It was longer than the gold/yellow trail. I was bored and just ready to get back. The blue path is super long and it wasn't much of a challenge. Part of this trail was along the main road, so it was a reminder that modern civilization was just beyond a few trees. I think the blue trail was more for people who are looking to take a stroll in the woods, or for people who are less athletic. Parking is $5 and you can pay at the machine on the lot. There are also a few picnic tables to enjoy a meal! There are a couple high points and peaks. It just feels great to say that you hiked up a mountain and made it to the top! So "just do it" and "take some time to enjoy the view!" read more

Finally found the time to do this hike after years whizzing by on Rte 7 wondering what it would be like! Overall a great hike -- quiet forest paths, boulders and caves, and fantastic views at the rocky top looking east and west -- all swathed in the romance of legend and history (a Mohican woman throwing herself off the top for love? Melville and Hawthorne meeting for the first time and hatching the idea for Moby Dick taking shelter in a cave during a storm?? I love places with these stories) The parking lot is easy to see right off Rte 7. There is a self pay parking kiosk, which costs $5 and there are trail maps and brochures. From the parking lot, there are two trails. The Hickey trail (yellow dot) is steeper and shorter, but definitely the one to take up the mountain if you can. Much more variation in what you can see, and the other trail (blue dot) parallels Rte 7 for the first part so you hear way too much traffic noise on that route (not exactly making for that feel of escape!). At the top you can link up with the Red trail which has the best views. The first part of it is rocky but totally fine, but the last part of it that connects with the blue dot trail was near these sheer cliffs and would qualify as a small adventure for me...it was even a touch scary actually (unless I'd strayed off path?) It's managed by the Trustees, which I think always does a good job -- the trails are generally all very easy to follow (which is NOT always the case hiking in MA where dead leaves just cover everything), and no trash anywhere. I spent about 2-3 hours up and down, including some chill time at the top. And I think it's fine for all levels, there were kids at the top and someone had their dog there too. read more

I love this hike as you can do a loop in less then two hours and that included stopping to enjoy the AMAZING views at the top. They have yellow, blue, and red trails and they can be a bit hard to see -- so you have to look at the tree markings so you don't take the wrong path to nowhere. Must be an East Coast thing -- they don't have these on the West Coast. A bit rocky here and there so I'd say you have to do some scrambling on the way up and down. Lots of rocks on the top but you'll be rewarded with stunning views -- go in the Fall for the leaves. Trails were pretty wide as we went during Covid -- so people mostly were masked up. Dog friendly too --they really love it! During the week we were there, there was a $5.00 fee via machine to park in the lot. Not sure if you can avoid this though. read more

Monument Mountain - Lots of shade / trees on the way up. - Hiking Near Me - Great Barrington, Massachusetts

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Good moderately strenuous. Beautiful view from summit. Convenient parking. Trails clearly marked.

Great hike - medium difficulty, some surprising moments and scenic panoramic vistas of New York and Massachusetts. Personally, I was pleasantly surprised how varied the hike was - it encompassed steep incline, spring waterfalls, rock climbing and some pretty slippery dirt roads. My advice to you is wear comfortable shoes with traction. Can get pretty muddy in certain areas. Definitely a must while visiting Stockbridge/Great Barrington. read more

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 yelpers 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. read more

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Like a walk in the park- then you will love Monument Mountain! Today was my 6th ascent and I still love it as much as my 1st. 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. read more

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Beautiful and somewhat challenging. I have lovely memories of hiking this mountain as a younger person .

Great hike! Not too long and just hard enough to make it a hike rather than a walk. Amazing views from the summit, if a bit crowded on an autumn Saturday afternoon. Make sure you go up to Devil's Pulpit, we saw many people pass by it, they missed out. Worth the $5 parking. read more

An awesome view and a nice hike. Two ways to get on the top, the easy and longest, the short but toughest. Also a nice hiking for pets and kids. Go check the trees during the fall! read more

Nice place the nature is so amazing love it. at the same time it is a slightly dark in winter and lonely place. But I love it I hope I am come back! read more

Do the Indian Mountain trial if you are a overweight, out of shape housewife from the Northshore. Halfway thru the trail I overheated & decided to turn back to our vehicle & crank the air conditioning. My husband trekked on. I stealthily / creepily followed a couple down the mountain bc I'm city folk & did not want to ruin my French Manicure or get eaten by a bear. At some points I jogged from fear of dying. 20 min later my husband ,who took the hardest route down, showed up dehydrated with a soaked t-shirt. We both drank tons of water & then proceeded to take a 2 hour nap when we got back to the motel. I highly recommend this hike. read more

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. read more

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. read more

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. read more

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. read more

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. read more

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. read more

Monument Mountain - Hiking Near Me - Great Barrington, Massachusetts

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. read more

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What a perfect hike. We took the blue trial to the end and then hung a right up the red trail to the peaks. (I don't recall the names of the trails, just the colors!) A little winded to get to the top peak. Once we were at the peak, we were very confused about how to continue on the trail. Their were massive boulders to climb over or you might could have gone around, but the boulders didn't seem stable. We asked 10 people sitting there and no one knew. Finally, folks came from the other direction and we had our answer. Mind, I am terrified of heights so am more cautious than most. However, some signage on the boulders would have been helpful. We circled back to the blue trail and back down. This hike is easy to mildly moderate. A lot of roots so need to watch your step. Definitely need to take water if doing the loop. Parking wasn't an issue and we were not charged on a Saturday in October. This is a trail I look forward to doing again. read more

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. read more

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. read more

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! read more

This is my absolute favorite hike in the Berkshires. I am a local and it's always nice to be able to go and hike up the mountain. The view is absolutely beautiful. Don't go on a weekend afternoon unless you want to be crowded with tourists I would suggest going on a week day then the mountain is peaceful and you can enjoy the view. read more

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. read more

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. read more