Roaming About

A Life Less Ordinary

Climbing Mount Greylock… the Easy Way

Ever since we arrived in Heath, MA to do this five month house sit, Mark has been interested in climbing the biggest mountain of the state, which is located an hour drive away. Usually I’m the first one to partake in any exciting hike or adventure, but ascending a 3500ft (1067 m) mountain is not in the cards anymore for me. Many times in the past, when scaling smaller hills and mountains, my “Sure, let’s do it! I’ll just walk at my own pace.” turned into tough, steep climbs with loads of sweat, many breaks and a guaranteed headache. Turning 40 is no joke!

Entering the mountain park

Entering the mountain park

Therefore, Mark plans to climb Mt. Greylock with a friend one day, after I drop them off with the car and take the lazy way up myself. But, who knows when that will happen and in the meantime, that mountain with its great views and variety of shorter hikes was just sitting there… only an hour away! When its draw became too great, I convinced Mark to come in the car with me, as a prelude to his hiking adventure. Dog Jenny didn’t need any encouragement. The plan: drive into the park, stop at pull-outs, enjoy the view, take photos, and be the quintessential tourist. It was bound to be a very easy and relaxing afternoon, the kind I used to thoroughly enjoy when exploring national parks all over the country. I just had to make sure not to drive Mark crazy with my never-ending “Stop here! I want to take a photo.” exclamations.

And so, the three of us set out to climb Mt. Greylock the easy way. The views at the pull-outs were expansive, but not too impressive. Plus, it felt like we were cheating. We passed many trails crisscrossing the whole area and hoped to stop at one of them on the way back, to visit some waterfalls. We could not come to this mountain without doing any hiking. It did not feel right. Close to the top, a sign with “$5 parking fee behind this point” welcomed us. “There is no way, I will pay 5 bucks to see yet the same view,” Mark said. “There is no way we will leave the top without looking over the edge,” I bounced back. We found a perfect compromise: we left the car at the second highest parking area for hikers and huffed the last half a mile up the mountain along a steep trail. It was free, we had some exercise, we felt like we somewhat deserved the reward at the top, and, best of all, I had “climbed the mountain” without succumbing to a headache.

Unfortunately, the observation tower with a 360° view was under construction. The alternative was to walk the four wind directions and have a glimpse of the surrounding area at points with or without obstructions. We have seen better views. But, we found 30 cents in a grassy area, which, the day we really need that to not run out of time on a parking meter, might save us $25 for a parking ticket. The thought we just saved $30 made us happy. 🙂

A sign for “Overlook Trail” drew our attention. Thinking it would circle the top of Mt. Greylock and offer wide views from different directions, Jenny, Mark and I set out into the shady woods. When after ten minutes we were still going down, deeper into those woods, without any chance of a view, we had a look at our map. What to do now? Instead of climbing back up and then down again to our parking area, we decided to make a big loop, and reach our car via connecting trails. Despite it being ten degrees Fahrenheit cooler than in the valley, it was a hot and relatively sweaty walk. Jenny panted heavily, so we took it easy and enjoyed a long break at the only viewpoint along the trail. Our big pancake brunch had been digested, so the snacks we brought were a most welcome sight.  When we reached our car, it was 4pm. The waterfalls will have to wait until another time.


  1. I hope you get a chance to go back for the waterfalls. I always think there’s something magical about them. Plus, it would mean enjoying more of these views 🙂

    • I love waterfalls as well. They are a great destination for a hike, especially on a hot day. I’m sure I can convince Mark to join me, or, I will visit the day he is doing his big hike.

  2. I’m still stuck on your “turning 40 is no joke” comment — wait until you’re closing in on 50! Ha ha ha. Despite taking the easy way up, Mount Greylock looks beautiful.

    Stephanie @ SV CAMBRIA

    • I had a feeling I might get comments like yours, Stephanie. 🙂 I realize 40 is not that bad in general, but, boy do I feel a lot of differences in my body compared to ten years ago. Of course, all those ailments worsened progressively over the years. The good thing: I feel much wiser and experienced in life. 🙂

  3. I like your way of saving $30! I’ve also enjoyed “cheating” with some of those mountains in the US that you can drive right up. Can’t think of any here – you have to do the hard work for the views 🙁

    • So, you mean there is no chance to be lazy in Scotland and still see the gorgeous views? How about a short stroll here or there to see a castle or a seascape. It must be possible! 🙂

      • Well yes, and I’ve also remembered there is a funicular railway up Cairngorm so there’s one mountaintop view you can get without climbing!

        • Great! Glad to learn there is some potential for lazy people there, but that is not to say that I don’t like a good walk, as long as it is not too steep. 🙂

  4. Wow, those are some beautiful views. I’m sure it was well worth the trip!

    On a more serious note, have you seen a doctor about the headaches? I’m 43 and can go on crazy hikes with little to no training (although I’m in good shape in general), with no ill effects. This definitely isn’t just a turning 40 thing. I’d say it’s worth seeing someone about, if you haven’t already.


    • Thank you for the concern, jmh. I used to have these headaches when hiking in the tropics (sweating in a hot and humid climate) and talked to my doctor in Belgium about it, every year I saw her. We tried drinking more water one year and taking a powdered solution the next. None of it helped. When she finally sent me in for an MRI scan, after I complained for five years, they found something else (that’s another story), but nothing that had to do with my headaches. I think the general consensus is “high temperature migraine” if there is such a thing. I think the blood vessels in my head are relatively thin. I will follow up on this again during my yearly physical in the US. Maybe the doctors are more helpful in this country (I’m pretty sure they are. :-)).

      • I hope so! Migraines are awful. The only thing that works for me is a medication called Zomig. Maybe it will work for you as well.

        • Thanks. I’ll look into that. So far, Tylenol kind of works after I lay with my eyes closed for an hour. Or, when I remember taking it preventively.

  5. So Ok, does being 54 also give me license to do those “partial hikes”? I ain’t as young as I once was either!

    • I give you permission, Keith! Although partial hikes don’t instill as much satisfaction, some exercise is better than none. And, it is a good thing to “know” your body. Although, I hate to give in to it! 🙂

  6. The views are lovely, Liesbet. The blue skies surely help 🙂 You don’t have to kill yourself to enjoy the great outdoors. I’ll be taking it very easy in the Algarve because it’ll be in the 30’s. Many thanks for sharing. 🙂

    • I’m not missing the hot and humid weather of the tropics when it comes to hiking. The climate is much more enjoyable here for “sweaty business”. Have a great time in the Algarve and enjoy your early morning or late afternoon rambles.

  7. Try turning 50 – that’s no joke either 🙂 I love how you found 30 cents on the ground. Frugality at it’s best!

    • I don’t mind getting older too much, except for the noticeable limitations. I guess that’s the definition of getting older, huh? 🙂

  8. That’s a great way to hike ~ we’ll certainly appeals to me!

    Ha ha wait til your fifties! But then again, how privileged we are to grow older.

    I used to get menstrual migraines… (No joke either) That’s one immediate benefit for me that has come with getting older. No menses no migraines.


    • So, you mean that there are some advantages to getting older? 🙂 Looking at the bright side of life is an attitude I love!

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