An Idiot’s Guide to Bolton Pond Trail

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Episode 1 of The Hiking Diaries

BoltonPondTrail (12)

I begin my hiking diaries series with a trail I’ve never hiked before. And it tripped me up. Hence the name of this post. It’ll all become clear as I go along. And I can’t even officially mark off this trail, because I only hiked a portion of it. Twice. In other words, I walked in circles.

But let’s start at the beginning. This is the beginning…

Bolton Pond Trail entrance

As I mentioned in my introduction to The Hiking Diaries, there is usually at least one special moment during a hike. Something that takes your breath away. Or something neat you notice. Or something that takes you by surprise, like the time an owl flew over my head.

There can be other surprises too. Like today. When Koda decided to poop right at the entrance of the trail. Not in the woods. Right on the trail. So I memorized the spot, walked back to the car, got a poop bag, found the poop, picked up the poop, brought the bag back to the car and left it outside so I didn’t stink up my car, then returned to the trail head.

Maybe I should have taken this as a sign that the hike was going to be no routine hike.


One of the first picture-worthy things I noticed were these dead trees. I have a thing about trees.

Along Bolton Pond Trail

Dead. But still standing as sentinels.

And right beyond them, a pine forest.

Along Bolton Pond Trail

I have a thing about pine forests, too. Really, pictures can’t capture them. They aren’t just in front of you. They are all around you. And if you’re like me, you become a part of them.


I soon came to this sign:

Bolton Pond Trail Sign

The weird thing about it is that there was a trail that went off to the left. And a trail that went straight. And a trail that went to the right, where this sign was pointing.

It is highly unlike Wachusett to not label the other trails. Highly unlike them.

And like a good hiker, I followed the sign. And went to the right.

One thing I noticed as soon as I went that way was the abundance of this ground cover….

Along Bolton Pond Trail

Wintergreen? My herbal brain started going into overdrive. I already found a huge stand of witch hazel on the mountain.

I plucked a leave, bent it, and smelled it.

It wasn’t wintergreen. I haven’t looked it up yet. I shall call it “faux wintergreen.” It was everywhere. And it would have been a great foraging find. Alas.


We passed by a big brook, with plenty of water. And this uprooted tree. Uprooted trees are a common sight on the mountain.

Along Bolton Pond Trail

Continuing along the stream, it became clear that Columbus wanted a part of it. So I brought the dogs down. And they drank and dipped. By dipped, I basically mean Koda laid down in it. She does that a lot when she is hot and tired and thirsty. But we had just started out on the walk, so maybe she just does it because she likes water.

And then… AND THEN! The most magic moment of all. We came upon Bolton Pond.

Bolton Pond

Yes, it’s beautiful. But the magic moment was when a great blue heron took off from the close side of the pond, and with it’s beautiful broad wingspan, flew just above the pond to the other side, in a slow motion movie that I captured in my mind. As you see, the water was mirror calm, and the gentle motion of the bird as it flew created a few seconds of peace that filled my soul.

The dogs went in the water. I wish I could let them off leash, to have a good frolic and swim, but Columbus wouldn’t have come back. I know this about him. He would have been after that bird and that peace that filled my soul would have burst like a bubble.


Soon after, we came to this spot.

Along Bolton Pond Trail

It is hard to tell from this picture, and I missed it the first time around, but there is a trail that goes straight ahead. It has a dead tree leaning in front of it. Tricky. But the larger trail goes to the left.

I went left.

See those two trees with blue markings like this in the prior picture?

Bolton Pond Trail Marker

Those are trail markers. And I missed them.


As we walked on, down the wrong trail, I took this picture.

Along Bolton Pond Trail

Because it always amazes me to find these stone walls in the woods, on a mountain. What, did people farm ON the mountain, at one point? Crazy.


Soon, I came to another sign that looked just like the first sign.

Bolton Pond Trail Sign

Because, um, it was. Only I didn’t realize it. I actually came out from the straight ahead trail. If you remember, I went to the right. And so, it appears, the trail circled around and came out back at this same spot.

Okay, now I was confused. And really curious. This loop wasn’t on the trail map. I decided to follow the trail that, in this picture, goes to the left.

I followed it, came out to another trail. Studied that carefully (okay, when I hit this dead pine tree and the trail forks left, take the left). Turns out I needn’t have worried. The dogs knew the way back.

I eventually got to this bridge.

Along Bolton Pond Trail

Kind of neat looking. Kind of rotted. But I walked over it without falling through and soon came upon a parking lot for the mountain where the ski facility stores all kinds of trucks and there is an outbuilding. Ugly. Did a 180, and pondered the following question….

“How the heck does this all relate to the trail map?”


I eventually wound up back at the trail entrance and checked my phone for the time, and decided I needed to figure some things out.

So I re-hiked the trail. Which is when I figured out that I had missed the correct trail after the pond.

And, what this means, is that I have to go back and do this again. Because, as it stands, I didn’t complete Bolton Pond trail. But I did hit some unmarked trails and explored them. Not part of the plan, but adventures do not go as planned.

Otherwise, they’d be boring.





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