Kent, CT to Wiley Shelter = 12.5 miles

Take off time. We started out under cloudy, cool conditions in the low 50’s. Despite predictions that there would be a) rain and b) no one else on the trail, the sun did break out of the clouds as a slew of Boy Scouts got on the trail right ahead of us – we would pass them eventually.

We climbed three elevations Day One-

Mt. Algo (elev. 1,190 ft)

Indian Rocks (elev. 1,330 ft)

Schaghticoke Mountain (elev. 1,331 ft)

The trail crisscrossed the NY/CT border as we continued climbing. We could see parts of the Housatonic River. At this point, the trail was incredibly rocky, and it inspired Young Dave to write a trail haiku of sorts.

Dead leaves over slippery rocks

All downhill


Right before the Ten Mile River Camping Area, we came out of the woods and onto the banks of the Housatonic. Incredible views, and we were surprised to see someone had a house right on the banks directly across from the trail.

We paused here for a break. This happened to be the end of the line for the Boyscout Troop – they met up with about 30 of their friends to camp for the evening. I was glad to be pushing on.

Our last climb of the day was Ten Mile Hill – while not ten miles long, the 1,000 ft ascent happens over a very short distance, and it took the last remaining energy we had. Young Dave had maintained the loathsome habit all day of steaming up inclines at the fastest pace possible. I had to inform him at that point that I was more of the “slow and steady” school, so while he was welcome to continue in the style to which he was accustomed, I would not be joining in that pace.

Luckily, we were a mere mile and a half from Wiley Shelter at this point. The remaining trail was fairly flat and leaf-covered, and we arrived with little incident. After declaring the shelter a bit too dirty to sleep in, we pitched our tents and ate a quick dinner. I think I was in bed by 9 pm.

I woke up that night to two things: first, a pair of Barred Owls calling to each other, and then, rain pattering on the fly of my tent in the wee morning hours. Fun.


click any of the names below for more information, including bird songs


Eastern Phoebes


Northern Goshawk


Barred Owl

Wild Turkeys

Canadian Geese

Pileated Woodpecker

Hairy Woodpecker