Damned Conn-ection: As indicated by the title, our friend The Old Leatherman actually stayed in this cave every 34 days, although with the uphill hike to reach it, this spot certainly doesn’t seem as if it’s on the way to anything or near something of note. Then again, Ol’ Leathery was the original social isolator, so ….
Noteworthy features/moments: This is a fairly rigorous hike over challenging terrain with dramatic elevation changes—the first half-mile is essentially climbing uphill the entire way as the trail goes straight over the top of a rocky ridge. In fact, there are some drastic ledges and drop-offs fairly early on. If you insist on wearing an authentic replica Old Leatherman outfit, which weighed about 60 pounds including the stovepipe chapeau—like we often do when out and about—this can be quite the workout.
Caution: The rocky path that comprises the second uphill section of the hike appears to be a wash that has been cut by centuries of flash floods, so this may not be a good hike to try on a rainy day.
The trail eventually winds up and around to a terrific overlook with a picturesque view of the valley (that you ironically may not be able to get a good picture of with a basic smartphone).
First-time visitors, be aware that the Leatherman’s Cave is actually under this overlook—if you continue on the blue-blazed trail, make sure to go left at the base of the rocks. Otherwise you might start going in the wrong direction until you check the GPS on your phone because the trail marking isn’t clear and the cave is not all that obvious (probably also part of its initial appeal).
The cave itself is surprisingly large and you can walk right in without any difficulty—if Shaquille O’Neal was wandering through here (because, you know, that’s a thing he does?), he wouldn’t even have to duck to enter, or at any point inside. The space is also clear and open, as there’s no doubt hundreds of people have been through here; if these rocks could talk, they probably would tell stories of countless campfires, illicit trysts, and twisted rituals. As caves go, you could do a lot worse for a spot to take an overnight.
Note: In keeping with social distancing protocol, you can enter the cave through one opening and leave through another.
Note 2 (Leathery Boogaloo): For some reason, this hike is not a loop, so even though the blue-blazed trail goes on past the cave, it will NOT take you back to where you started … unless you decide to do the Old Leatherman’s entire 360-mile circuit. Good luck with that!
Damned Verdict: This is an opportunity to connect with one of Connecticut’s most enduring legends—how do you walk away from that?