Monument Mountain, Massachusetts – Roulette Hike Review

Standing at one of the viewpoints along Monument Mountain's Summit Ridge - Great Barrington, Massachusetts


After taking clients through the Ice Glen Trail a few miles away, I passed by the trail sign for monument mountain. And, if I pass a sign for a mountain I was previously unaware of – I’m gonna stop. And I’m glad I did, as this was a great little hike with some nice features and views along the way. The three mile loop gains about 700 feet of elevation and passed by a small waterfall before you reach the 1,600′ summit and ridge. From there, you’ll see incredible rock formations (one being the ‘Devil’s Pulpit) and views of the surrounding Great Barrington area. Just 2.5 hours from New York City, this hike makes for a great day trip, or quick overnight in the quaint town nearby.

Monument Mountain Reservation Trail Map
  • Total Distance: 2.8 miles
  • Elevation Gain: 685 feet
  • Difficulty: easy with a few slightly moderate scrambles
    • Ledges and viewpoints have steep drop offs
    • Expect ice on trail from November – March
  • Markers to Follow
    • Hickey Trail (Yellow Markers) from Parking Lot to Squaw Peak Trail (Red Markers)
    • Squaw Peak Trail (Red) to Indian Monument Trail (Blue) and return to parking lot
  • Crowd Factor – very busy on weekends, limited parking
  • Trailhead Location: Monument Mountain Parking Lot – 545 Stockbridge Road, Great Barrington, MA 01230
    • Note: there is a $5 fee to park
  • Recommended Gear: The Essentials, Microspikes from November to March

The Ascent

Large boulders line the trail that winds through the forest on the way to Monument Mountain’s Summit

If you’re used to tackling peaks in the Adirondacks, Catskills or White Mountains, the ascent here won’t take you on a thrill ride, but its nonetheless a very pleasant hike. You’ll gradually pick up elevation as you wind through the forest and around large quartzite boulders. For a short section you follow the trail along a stream that leads up to small waterfall as you continue up the trail (shown below). After a lot of rain, the one stream crossing might be a little tricky, but it wasn’t too bad when I went in late February.

You’ll continue on the Yellow Trail for another third of a mile and a few sections that are a little steeper or trickier to work your way through if there’s still some ice like there was this day. Below, you can see one of the quasi scrambles that required using your hands a bit to get up and through. At just over a mile, you’ll come up to the junction with the Squaw Peak and Indian Monument Trails – take the Red Trail to Squaw Peak.

From there, you’ve got less than a half mile to go to reach the summit and the ridgeline, and you’ll get a few open views along the way looking out onto the valley below. I spent a few minutes at each of the viewpoints as I continued down the ridge. There are sheer drop offs on either side of the ridge, so be sure to watch your footing when getting near the edge. Also, much of the ridge’s shady area still had some ice, so I made sure to throw microspikes when working my way through here.

The Summit

Sitting at just above 1,600 feet above sea level, the summit offers views in nearly all directions (including ski mountains in the distance) and beautiful rock formations.

View of Monument Mountain’s Summit

Once you’ve spent some time enjoying the viewpoints, you continue down the ridge to make your way to the ‘Devil’s Pulpit’ – a dramatic rock spire that has broken away and tilted off from the mountain.

The Descent

From the Devil’s Pulpit, you’ll take the Blue Trail (Indian Monument Trail) back down the loop and then back to the parking lot. It’s about 1.5 miles from there, and nothing too difficult aside from a few small boulder piles. Overall, this was a great quick hike thats perfect for both beginners or those looking to keep their legs fresh!

Video Review

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