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Great Barrington, MA

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Monument Mountain - Squaw Peak

5.0 (1 review)

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10 years ago

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Housatonic Flats - River

Housatonic Flats

2.5(2 reviews)
2.2 mi

Very easy walkable trail outside of Great Barrington (just across from Barrington Brewery). There's…read morea small sign off the side of the road for "Housatonic Flats", with a nice gravel parking lot. There isn't too much information (such as flora/fauna markers, historical notes, etc), but the signage that they do have is in great condition. At the trailhead just past the gate, there is a bulletin board with a trail map on it. There's only one trail as of the writing of this review: the Loop Trail which is 0.8 miles in length. It's obviously a loop, so whichever direction you choose, you will end up back at the trailhead. The trail itself is very walkable, great for a causal afternoon or evening stroll, and doable for all ages and abilities. It meanders along the river-- and there's a couple of side paths that head towards it-- but the banks are very steep. Use caution when walking off the main trail. There is very little incline over the course of the trail, and is mostly trimmed grass. It's very well kept up. When we visited, there were quite a few beautiful wildflowers in bloom. I'm sure that if you took your time, you'd get to observe some regional fauna, too. There's only one bench on the trail, which over looks the river. Aside from the mown trail, the rest of the Housatonic Flats park is mostly thick meadow with a treeline near the river. I'd advise staying on the trail to minimize nuisances such as ticks, poison ivy, and mosquitoes. There's no place to picnic or BBQ, so I'd advise saving that for another area altogether. It's a very nice path for a quick scenic walk. Enjoy it while it's still relatively unknown!

I didnt love this hike. Went in aug 2018 which was a very hot and humid month. We always hike…read moreearly so in by 730. Very buggy. Not very pretty. I think everyone else knew it too as this is the first time i have ever hiked and not bumped into other people. Hike is also very short. Would not recommend when there are so many other nice hikes around

Photos
Housatonic Flats - Flowers

Flowers

Housatonic Flats - Signposts

Signposts

Housatonic Flats - Map

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Map

Housatonic River Walk

Housatonic River Walk

3.2(5 reviews)
4.0 mi

I visited this trail today for the first time. I really enjoyed the view of the river…read moreand the serenity. The path is flat, with blue crushed stone and quite wide so even someone with a wheelchair could navigate it. At times the river falls out of view and comes back again while the trail takes you through meadows and more populated areas of the town. A great way to get out and enjoy nature in Western Massachusetts.

"Hey, babe Take a walk on the wild side"…read more(Lou Reed) Great Barrington, MA was founded way back in 1738. So what did the town do to celebrate it's 250th anniversary? They staged a cleanup of the Housatonic River and volunteers removed 15 tons of debris from the riverbank. This was the start of a river restoration project that culminated in the creation of the Housatonic River Walk. The River Walk was built in two sections known as "Upstream" and "Downstream". We walked the Upstream section yesterday. It runs from the River Walk bulletin board at 195 Main Street to the William Stanley Overlook. The entrance has a pretty steep staircase, so you'd best be paying attention and not be texting with your BFF. The trail is short, but has some gorgeous views of the river on your left. This portion of the trail ends at the William Stanley Overlook - a nice observation point where you can admire the view and learn about Mr. Stanley, a local inventor who developed an electrical transformer. His 1886 breakthrough was responsible for running electrical wires across the river to transmit power to stores and offices on Great Barrington's Main Street. The upstream section's exit is a staircase going up to the St. Peter's Church parking lot on Dresser Avenue. This worked great for us, because we had conveniently parked our car there. It's not the longest trail we ever walked, but it was one of the more interesting and scenic walks we've taken.

Photos
Housatonic River Walk - Meadow Trail

Meadow Trail

Housatonic River Walk
Housatonic River Walk

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Monument Mountain - The blue trail

Monument Mountain

4.6(28 reviews)
0.2 mi

Great place to hike and enjoy the outdoors!…read more 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!"

Beautiful trails and an amazing view from the top. We arrived around 11AM on a fall Saturday and…read morethere 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.

Photos
Monument Mountain - Smiley

Smiley

Monument Mountain
Monument Mountain - View from the summit

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View from the summit

Monument Mountain - Squaw Peak - hiking - Updated October 2026

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