Stealth Camping, Great Barrington, MA

Stealth camping in Great Barrington under a sky that threatened rain but never delivered. I laid out my sleeping pad and bag directly on the grass, no tent, just open air and the possibility of getting soaked. A half gallon of milk, and a flashlight that probably gave away my position to anyone who cared to look, but I was too content to worry about it.

Wandering north through the Berkshires with no urgency, I’m ahead of schedule for a friend’s wedding. The only thing that waits somewhere up the trail, the single appointment giving my life any structure at all.

The trail wound through stands of tall pine and hemlock, my feet crossing boardwalks built for seasons wetter than this one. At a road crossing, I almost missed the hand-painted sign.

Trail Stand. Snacks & Soda.

A closet-sized shed on the roadside. Honor system payments. I ate four ice cream sandwiches, drank two cans of Coke, and dropped four extra dollars into the ether, just in case someone else forgets.

The trail is about recognizing that you’re part of something larger than your own hunger, your own thirst.

Life is too good sometimes.

#appalachiantrail #wandering #hikertrashforlife #trailmagic

Alice Monthly Update - September 2025
Jenny's Cabin