King Philip’s Caves

King Fillup the Life Star
King Philip’s Caves, Simsbury
November 2024

Don’t do this.

Seriously, local search and rescue teams are tired of dragging broken bodies from this area. So many broken bodies over the years that they have put a Life Star landing pad as close to future broken bodies as possible:

And that’s right where you’ll want to park in order to get to King Philip’s caves! (But don’t do it.)

And then you find the easily found trail over the back rail at the end of the road/landing pad and head south. (Which is a perfectly fine trail.)

It’s when you reach a branch that you should veer left and connect up to the yellow-blazed Tower Trail that will give you great views of the Farmington Valley and western Connecticut, ultimately bringing you to Heublein Tower. (Do that!)

If you, for some reason, take the right trail at that fork – the one with the “Please Stay on Trail” sign pointing to the left (which was nearly buried in the leaves when I totally didn’t notice it), be careful. This is not a maintained or sanctioned trail. And if it’s wet or icy, you better know what you’re doing.

So what was I doing? I didn’t really know. As the “guy who does everything there is to do in Connecticut,” including caves (and “caves”), I was at least curious about King Philip’s Caves. I had just come from searching for Simsbury’s Hell Hole, which required a walk down Route 185 – arguably more dangerous than this trail which took me under massive cliff walls along a poorly constructed trail.

I’d been holding off on this trek for years, but now that I was in the final stretch of CTMQ-completing Simsbury, it was time.

Between 1648 and 1661, Indian lands were gradually deeded over to the Englishmen. In 1670, the Massacoh Plantation came to be named “Simsbury”, probably after Symondsbury, Dorset, England. Many of the earliest English settlers came from Dorset, including Thomas Ford, the first to clear land and farm here.

In 1676, Indian disputes erupted into King Philip’s War, and in March Simsbury was attacked by a group of Philip’s warriors and burned to the ground. According to legend, their leader, King Philip, sat in the large cave on Talcott Mountain to view the spectacle. It is still called the Metacomet Ridge.

“King Philip” was the weird name given to the Massacoh chief Metacom. I highly doubt he climbed up here to sit in a cave to watch Simsbury “burn to the ground,” but hey, we had to make monsters out of the enemies, right?

You’ll notice I’ve written King Philip’s “Caves…” plural. There are two. Once the sketchy trail meanders below the cliff faces, keep your eyes peeled for the first “cave.” It’s about a 12 foot climb from the trail. Oh, and of course it’s not a cave – just an opening in the cliff face.

The deeper cave is far less accessible. It’s about a 60-foot climb up from the trail, up a class 4.7 rockface. I would not want to fall trying to get into that “cave.” You can supposedly climb down from above, but seriously, really don’t do that.

There have been ropes placed in the past, but who knows how reliable they ever were. Here’s a video of a guy ascending via a rope from 2014:

There are plenty of internet tough guys who say they’ve free-climbed that on their own. Good for them. This rational married father of two wasn’t about to try.

I was satisfied with being below the larger cave and with scrambling up to the smaller one.

Look, these caves are dumb. The views from the Tower Trail above are infinitely better and the trail is infinitely safer. These aren’t real caves at all and there’s really no point in seeking them out. Unless you are a very skilled free climber, don’t bother. And if you are, and you fall, get your friends to rescue your dumb butt.

And lastly, Metacom or Metacomet is an infinitely better name than King Philip.