Climbing to the Highest Point in Massachusetts.

The summit of Mt. Greylock

Climbing to the Highest Point in Massachusetts.

For me, hiking has always been a form of therapy. There’s something different about the world from inside the woods. Problems don’t seem as big, worries don’t seem to matter, and the world is silent, except for the sounds of animals going about their day. For me, hiking is peaceful, at least that’s how it usually is. My experience climbing to the highest point in Massachusetts was the complete opposite.

When I made my goal to hike to the highest points in each state, I knew that there would be some difficult hikes, but those were ones I’d eventually get to and prepare for. As far as I was concerned, Massachusetts was going to be an easy one. But, quickly, I discovered just how wrong I was.

In many ways this is my fault, choosing the quickest trail up, which is also the steepest, and not preparing myself for the hike ahead of time. I only have myself to blame, but the feeling of reaching the summit of Mt. Greylock was one of the greatest moments of relief I’ve had in a while. Still, as difficult as it was, I learned a lot from the challenges I faced along the way.

So happy I could kiss the summit!

Mt. Greylock stands at 3,491 feet in the Berkshire Mountains of Massachusetts, and a two hour drive from Northern New Jersey to Adams, Massachusetts. We parked near Gould Road, and after getting settled, we got our gear together and were ready to hit the trail.

Climbing to the Highest Point in Massachusetts

The mountain was engulfed in a cloud and it started to drizzle, so we made sure to pack our rain gear. For August, it was a relief that the air was cool, and I was feeling confident the moment I stepped foot on the trail.



That confidence would quickly wane as soon as the trail we were on became the Thunderbolt Trail, moderately difficult but steep. It wasn’t techinical, but I was in no shape to be hiking it under the time constraints we gave ourselves. Since we didn’t arrive in Massachusetts until the afternoon, we had to make sure we were able to get up and down before dark.

Looking back, I probably should have done a bit more research into what trail I was taking up. My goal was to get up and down quickly, not realizing there would be any problems along the way.

Thunderbolt Trail

On our way up, we traversed through small trails with overgrown wildflowers full of bees harvesting their pollen. The rain had stopped, but the trail was muddy and any rocks we encountered were slippery. This made for a difficult way up. Not only was the steep incline hard on my legs, but the slick surfaces didn’t help. The entire trail was uphill, and my legs were not as strong as they needed to be.

The trail was unlike previous trails I’ve been on, and with our goal, I barely had time to appreciate the beauty of it. It felt like another world, and at one point I commented that it felt as though we were in Jurassic Park, especially as we neared the summit and the cloud cover became a mist surrounding us.

The Big Bend

This was also the first time I had several wildlife encounters while hiking. In the past, it had been limited to birds flying overhead, the occasional chipmunk, and once a deer. But, this time, a snake scared me as it slithered across the trail just feet ahead of me and a frog jumped out of my path just before I stepped on it.

Eventually, after much complaining, and wondering why I ever thought hiking the high points was a good idea, we reached what I thought was the summit, only to be disappointed by an intersection with a road. In front of us was a path full of rocks that would be the last stretch, and I stood envious of the cars easily making their way to the top.

One last stretch to the top

Just over a few more slippery rocks, the summit was within our reach. Seeing the signs, after thinking they were coming for two hours, made my heart sing with joy. The toughest part was over, at least the rest of the journey would be downhill.

Monument on the summit

Unfortunately, the cloud cover didn’t give way and there was no glorious view to speak of. We snapped a few photos, ate a snack, and got ready to head back down. It reminded me of my time on Mt. Marcy, where the view so many speak of was also completely blocked due to cloud cover and winds. We also had limited time to get off the mountain before dark, and in both instances, after all that hard work, there was no time for lengthy celebrations.

The summit of Mt. Greylock

Instead, it was a straight shot down the mountain, which often included a lot of thinking as to where to step to avoid falling. I had one big fall, hurting my knees, but nothing that stopped me from getting off the mountain before dark fell. By the end, I was exhausted, my body hurt, and I wasn’t even grateful for finishing the hike. Instead, for the first time in my life, I never wanted to see a trail again, let alone hike one. All I wanted to do was shower, eat, and go to sleep.

Finally done and just before the sun set!

I’m not sure why my attitude was so poor for the majority of this hike, but for whatever reason, even the feeling of getting to the summit wasn’t enough to shake me out of my funk. We decided to cancel our hike in Vermont, reserved a hotel nearby, filled up on food, showered, and went to bed.

In the morning, I woke up a new person, not as sore as I thought I would be, and finally proud of my accomplishment. No matter how hard it was, I had chosen not to give up. I made it to the top and had added a fourth highest point to my list, and I knew that I wanted to continue to add more.

Still, the hike had served as one full of lessons. The first one being that I’m not in the shape I need to be, even though I’m at a healthy weight and am relatively active. My legs didn’t have the strength they needed in order to have a successful hike. If this is a goal that I’m serious about, and one that I want to make a reality, then I have to take conditioning and preparing for a hike more seriously.

I also learned that it’s probably important for me to become more informed about the wildlife I may encounter on specific trails. While the animals we encountered weren’t dangerous, seeing them made me realize that I could meet anything in the woods, and that I probably should be more aware of what I should do if I come across certain wildlife.

Along with that, would be learning basic wilderness first aid skills. The rain made the trail dangerous in several areas, and even though I only suffered bruised knees, I’m not sure what I would have done if I had had a worse fall. I’d like to at least learn a bit, so I’m prepared and able to take care of myself no matter what the situation.

Finally, I’ll give myself more time. Part of the stress on this trail was that we arrived late, which put us at risk for afternoon thunderstorms and we had to worry about it getting dark. There was no real time to rest up, and we had to hustle up and down the mountain. My favorite part of hiking is being able to take it all in and enjoy the beauty surrounding me, but that was not possible during this hike.

Heading down

I may have learned many lessons, but I also learned the importance of not giving up on a goal. The next morning, one of the friends I was with suggested heading to Rhode Island’s highest peak on the way home. I’d be able to reach my fifth high point before the end of summer, and it was a short, easy hike after a long day on Mt. Greylock. My initial reaction to the suggestion was pure excitement in getting back into the woods and continuing my goal. I know it’s not always going to be easy, but I’m determined to find a way to make it happen.

Spread the love

Comments (5)

  1. Walking to Rhode Island’s Highest Point. | The World Wanderer

    […] ← Climbing to the Highest Point in Massachusetts. […]

  2. Traveling Ted

    The outdoors can be humbling at times. I have been on a few hikes lately that were more than I bargained for due to lack of water and lack of research on the water conditions, so I know how you feel.

    1. The World Wanderer

      It was a really rough day, haha. But this weekend I’ll be taking on Vermont, and I spent all week really preparing. Here’s hoping my legs are stronger and my attitude is positive! 🙂

  3. Marina from

    I can totally understand all of the feelings you had during this 😛 We also just went hiking and it was darn tough… first time. Looking forward to reading more of your posts.
    Marina from

  4. Failing to Reach the Highest Point in Vermont. | The World Wanderer

    […] in fear, in fact, it was one of my best hikes to date. I had been training after my experience in Massachusetts and ran almost every day and worked on strengthening my legs to ensure a good hike. Physically, I […]

Post a comment