[On May 17, 2026, I posted a thread to Mastodon about my plan to attempt to visit every Trustees of Reservations property in Massachusetts. My intention was to post threads about all of these on Mastodon, since at the time, I was not auto-deleting postings to my Mastodon account. Since then, however, I’ve decided to auto-delete my old postings, and I want to preserve the threads about my Trustees visits, so I’m gradually backfilling those threads onto my blog. This is that first thread, posted May 17, 2026.]
May 17, 2026
Yesterday I was sitting around in a funk because I’ve been unable to find a meatspace community with people I want to be with doing things that I want to do and I’m increasingly skeptical that I will. Furthermore, it was beautiful outside and I didn’t want to waste it cooped up inside doing chores, but I had no idea where to go.
Then an idea popped into my head.
A few months ago, I read an article in The Trustees of Reservations <https://thetrustees.org> magazine about a guy who’d visited every single Trustees property (or maybe it was a Mass Audubon <https://www.massaudubon.org> article about a guy visiting every one of their properties, the details are fuzzy at this point). I said to myself at the time, “That sounds kind of fun, but my free time is already over-subscribed, so it’s not for me.”
But yesterday, looking out at the beautiful weather, with nowhere else for me to go and no interest in doing what I was “supposed to” be doing, I reconsidered.
“It’s not like I’m signing a blood oath,” I said to myself. “Maybe I won’t end up visiting every Trustees property, but there’s no reason why I can’t visit one today.”
So I scraped a list of all the Trustees properties from Wikipedia <https://en.wikipedia.org/wiki/List_of_properties_managed_by_The_Trustees_of_Reservations> and literally randomly picked one. The computer decided I should go visit Dry Hill Reservation in New Marlborough.
That’s about two and a half hours’ drive from my house, but what the hell, let’s go!
Before I could have second thoughts, I threw on my riding jacket, helmet and gloves, hopped on my motorcycle, and hit the road.
About two and a half hours later, after one stop for gas and a bit of a slow-down at the end getting the motorcycle safely over the gravel-covered roads approaching the reservation, I arrived.
It seems this isn’t a popular Trustees property, which makes sense since it’s kind of in the middle of nowhere. There was one other vehicle in the small parking lot, and I ran into its owner later on the way down from the summit when I was on the way up. I didn’t hear or see anyone else while walking miles of trails, and when I got back to the parking lot my vehicle was alone, so I’m pretty sure the other guy and I were the only two people to visit in the couple hours I was there.
It’s a lovely little reservation. Here’s the map posted by the parking lot.
The hike to the summit is a spur off the main loop trail, so if you don’t want to do that part of the hike, which is a bit steep at the end though not really treacherous, you can just do the loop trail. The loop trail is all woods, perhaps not impressive enough to warrant a 2½ hour drive 😉, but if you live closer than I do, it may be worth the trip. Also if you have a dog. There are SO MANY sticks. Dog heaven.
A brief aside about trail blazing…
IMO there are two main approaches to trail blazing: “adequate” blazing and “reassuring” blazing. “Adequate” means the blazers ensure that there’s just enough blazing to ensure hikers won’t get lost, but they may feel a bit nervous along the way. “Reassuring” means there’s never enough of a gap between blazes to make hikers nervous. Alas, I am a nervous hiker, and Trustees trail blazers seem to prefer the “adequate” approach.
Weirdly, neither the sign posted on-site nor the trail map available for download from the Trustees website indicate the blaze colors for the two trails. If I recall correctly, the loop trail is blazed blue and the summit trail is blazed yellow.
I passed by / under this semi-fallen tree on the loop trail. The photos of it below from both sides don’t quite capture the grandeur of it because I am a bad photographer, but I thought it was impressive enough to share.
I saw some enjoyable small flora during the hike.
There are a lot of interesting boulders and exposed bedrock along this trail. Here are a couple that struck my fancy.
Eventually I made it to the summit and stood there, listening to the wind blowing through the hills and trees. It was beautiful. Here’s a panorama of the view from the summit looking southwest at the Berkshires (click through for the full-size image).
I took this photo lying on my back on the bedrock at the summit, looking straight up at the sky:
Here’s a selfie of me at the summit, with the view behind me. “Why are you wearing an undershirt?” Well, as I mentioned above, I rushed to put my plan in motion before thinking about appropriate hiking clothes. By the time I got to the summit I’d stripped off my riding jacket and flannel because of the heat and exertion.
In closing, I leave you with a one-minute soundscape of the wind and birds at the summit of Dry Hill Reservation. Sound up, close your eyes, and enjoy! If you listen really hard you can feel the wind on your skin.
