Monument Mountain, Squaw Peak and the White Whale



Last Friday while in the Berkshires for Thanksgiving, I went back to Monument Mountain to settle some unfinished business.

A few years ago, when we were there to get our season passes at Ski Butternut and ride the chairlift for some fall leaf-peeping, we also did a hike up Monument Mountain and its second summit called Squaw Peak.

The mountain is located right on Route 7 between the towns of Great Barrington and Stockbridge, in Massachusetts. I found the hike in a book about great hikes for kids, which makes my freakout story all the more amusing, and we will get to that.

I was not quite as A.T.-obsessed at the time, believe it or not. So I didn’t realize that my now-favorite trail traverses the ridges just a few miles to the East and West of this mountain. And that sweeping views of the many summits on the A.T. and far beyond are laid out in all directions from its rocky peak. So this time around, I really appreciated the those views. We will be traversing those very ridges next summer as we head northbound into Massachusetts from where we left off last summer at Sages Ravine.

Now before I get to my story, here’s a little bit of the fascinating stories the mountain has to tell.

Granite walls

Granite walls on the Squaw Peak trail

Legend has it that Squaw Peak was named so because a Squaw was flung from it for falling in love with a brave from another tribe. Whether this is true or not, and there are lots of similarly-themed stories involving other local peaks, its a captivating one for sure. And while standing at its ledges, one is sure that the significant drop from these precipices including those across the chasm from the ‘Devil’s Pulpit’ are surely dramatic and life-ending. I will leave her story there for you to research further at your convenience.  And since I’m sure you’re probably curious about the ominously named structure called the Devil’s Pulpit, it’s a tall rock pillar that hangs off the sheer wall of granite on the southern end of Squaw Peak. You can see it in the shot behind me below, just to my left.

Then there’s the other legendary story on Monument Mountain, and this one is known to be confirmed. In 1850, local author Nathaniel Hawthorne and his friend Herman Melville (maybe you’ve heard of them?) were hiking the mountain when they were caught in a nasty lightning storm, forcing them to seek shelter overnight in a cave. It was at this time that perhaps a combination of the two authors sharing seafaring stories that they enjoyed like any literary 1800’s New England-er would, as well as the humped shape of Mount Greylock which is visible in the distance, that the idea for Melville’s famous novel, Moby Dick was conceived.  Correct me if I’m wrong about any of this. I prefer to believe these legends and the romanticized notions they hold.

Though all the way at the other end of the state near the Vermont border, Greylock is Massachusetts’ highest peak at 3,491 feet and this is why it is visible nearly 50 miles away from the 1,642 foot summit of Squaw Peak.

Mt Everett and the Taconic Plateau

Mt Everett and the Taconic Plateau

Heading up the Hickey trail on that first hike, the beautiful yet typical wooded path led us to the base of the peak. From there at “Inscription rock,” it climbs up a steep root and rock-strewn line a hundred or so vertical feet to the summit. At that point, all you see are a few boulders and the straight drop offs on either side of them. I have a bit of a fear of heights that I’ve worked hard on since this original hike to conquer, by traversing many miles of local trails with similar topography. 100 more miles of the A.T since has also helped with this, and obviously as someone who wants to complete the whole trail before I die, I have to get over these things. I was very pleased with the improved results this time around. Under different circumstances I might have just braved it then and there and been done with it.

Me at the Devil's Pulpit overlook

Me at the Devil’s Pulpit overlook

But on that beautiful day as on this one, the mountain was crowded with adults as well as many a fearless child, including my own. Ah to be young again… I learned to ski as a toddler so I will ski just about anything no matter how hairy. Its a funny mental phenomenon. I am also a snowboarder, but since that sport was not introduced until my late high school years, I never learned or dared learn to do things like jumps or half pipes on my board. This of course is because gravity, and my rational near-adult fear just wouldn’t allow such bold actions that I would surely have done, and would have been much easier as a younger child. Any time I’ve tried them since have resulted in pain.

Greylock to the north

Greylock to the north

Anyway, I digress. Back to the humor. The adults and kids were lining up behind me and scrambling around me from both directions. My own kids moved on ahead and posed for photos together upon the highest boulder I could see on the summit. At this point I froze. I shrieked for them to stop, not knowing that they had already tackled the most dangerous part at that point (which really wasn’t that dangerous if taking a little time) and there was no threat whatsoever at this point that they could fall off this boulder thousands of feet to their deaths. As I now know, beyond that was plenty of wide berth and plenty of other rocks that would prevent any danger. All I could see from my particular vantage point was my kids perched upon a cliff.

So at that point I begged them to turn around to prevent any further harm to them or my pride, and we headed back down taking another flatter trail to the lot. I felt defeated, but also that my protective impulses were warranted as a parent and I could live with that. But it didn’t sit well for long, because I felt silly, humbled and beaten by something everyone else had no problem at all achieving. I guess we all have to learn somehow. I still saw the same perspective on this hike as I descended from the other direction and felt a little better that it still did look a little sketchy. But I let my fear of the unknown win that day. And I was back today to finish this and enjoy it in full.

Atthe summit of Squaw, Everett beyond

Atthe summit of Squaw, Everett beyond

This time we came up the other direction, starting on the flat trail but ascending the peak in a much steeper, faster route on the Squaw Peak trail.  I enjoyed the challenge, bolstered by the experience I had built since our first time here. I ventured out many times along the trail to other steep ledges to take in the Western and Eastern views as we ascended.

At the Devil’s Pulpit path I scrambled down to the very edge of that perch, alone at first to prove to myself I could, then with Fielden so she could take in the view and get great photos, of course! At the main summit we climbed onto the same boulder my kids did and got a nice shot that some other hikers took, and some panoramic video. I was so excited I forgot to have a snack and couldn’t wait to get back down to meet our families for lunch and let them know I had conquered what was my own white whale. Melville would have been proud. I feel ready for anything the trail throws at me, Well, almost anything.

Inscription Rock

Inscription Rock

It was also great that despite hearing they were now charging parking in the lot, REI’s #optoutside campaign to encourage people to enjoy Thanksgiving and Black Friday in the outdoors instead of having to work, had inspired those that manage this reservation to give free parking as a reward for doing so. I’m proud to be a member. Many other retailers also followed suit and closed their businesses at least for Thanksgiving day.

Before we left the Berkshires, I took the whole family to the Shay’s Rebellion monument (Google it, people, this thing is getting long!) on the A.T crossing nearby for some history, white blazes, and more views of what we had in store next summer.  I highly recommend this hike.

There ARE several dangerous drop offs as a matter of fact so keep any very small children close by, but you are all guaranteed to have a great hike and even greater views as a reward!

— Linus


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