If you didn’t know it before, you know it now. We are early morning people! Four hours from home in York, Maine lies Caleb Peak on the Appalachian Trail near Kent in western Connecticut. To beat the Hartford, CT commuter traffic two and a half hours away, we set our alarm for 4A. Off by 430A, we will not see sunrise til well after 7A on this late October morning in New England.

State of Connecticut (We hiked near Kent in the central part of the western green section of the map.)
Sailing through Hartford on I-84, we are quickly dumped onto suburban roads heading west. Just after 7A, the school buses are out; parents driving kids to school line up to turn left into the school lot. Dunkin’ Donuts, Cumberland Farms, and traffic lights keep us well under the 35 mph speed limit. Patty’s Restaurant in Litchfield, CT, thirty minutes from our trailhead in Kent, CT, is our breakfast destination.
Ordering two eggs (over easy for me, over hard for Hannah), home fries, and toast for $4.25 each, we have ourselves a very basic breakfast; one that is hard to screw up. And they don’t. What I am reminded of is that a good breakfast does not make it a good breakfast experience. Hear me out.
For me, a good breakfast experience is complete with an engaging waitress. On this morning, there are customers at only one other table in a restaurant of 12 to 15 tables. So the waitresses have time to engage. They are nice enough and attentive, but they don’t know I love to interact. They are not mind readers!
It is I who blow it big time by not initiating the conversation and giving them the cue to fully engage with us. I can make the excuse that I am groggy from driving 190 miles in the predawn, but a mirror shows who dropped the ball; so Hannah and I are filled but not satisfied. I’ll do better next time. I promise.
I am amused when I go the men’s room.
Just 30 minutes from our trailhead in Kent we wind along rural roads, appreciating the country homes out in the woods; and so very thankful that we live near town ourselves.
Arriving on Route 341, we blink and miss the town of Kent; we then cross the Housatonic River and turn right on Skiff Mountain Road at the playing fields of the Kent School.
It’s a mile on Skiff Mountain Road to a right turn on River Road, which we have been warned is not paved but gravel. (We get excellent directions at this link – Caleb Peak Trail).
River Road hugs the Housatonic River, and about a mile later Hannah’s eagle eye spots the very small AT sign at the trailhead.
Today will be my 9th of 14 AT states. Previously (going south to north), I’ve hiked the AT in Virginia, West Virginia, Maryland, New York, Massachusetts, Vermont, New Hampshire, and Maine. By the way, Hannah has run on the AT in North Carolina and is one up on me.
Though it’s only 1.2 miles of hiking to Caleb Peak, we see a mountain of stone before us; the guidebook promises 99 steps to make our way to the summit. Heading south on the AT towards the looming mountain across from the Housatonic River, we are here in late October and most of the leaves have fallen.
Our sometimes rocky trail is covered with brown leaves, but the white blazes (painted 8 inch splashes of white paint) on the trees and rocks guide us without fail. On the slowly rising ground our foot placements are deliberate and steady due to the leafy-covered trail.
Within 0.2 of a mile we are climbing by grabbing rocks to maintain our balance. The rocks are irregularly placed and in no way seem like the advertised 99 steps. Breathing heavier, we drop the conversation as I follow Hannah onward. Fortunate that we only need fanny packs for our water and gorp, I can’t imagine lugging and balancing a 40 pound pack (common for AT hikers) up this precipitous rocky mountain edge.
And then we hit the 99 stone steps. They are a godsend in negotiating this mountain wall with steady, sure, solid foot plants.
It’s hand-to-hand combat as we assault the mountain to the St. John’s Ledges which looks over the river valley; in 25 minutes we’ve gone just 0.5 of a mile.
Soon the trail levels out and our conversation begins again.
It’s an easy 0.7 mile further up the mountain to the lookout at Caleb’s Peak.
As hikers know well, the trail down is tougher than climbing up. Ascending has us sweating beneath our shirts, but climbing down we are wary of sliding on rocks, especially this time of year when the trail is entirely covered with dead yellow and brown leaves. Often we climb down side saddle or even backwards to maintain our balance.
And then it happens, first I slip on my butt, then Hannah does; each time we bounce back up, fortunate not to have twisted an ankle or knocked a noggin. Our guardian angels are working overtime today. We don’t see another hiker all day and it is clear that this would be no trail to climb in wet weather.
In just under two hours we are back at the trailhead and still want another hour of hiking. We head north on the AT now, which is the aforementioned River Road.
In less than a mile the road becomes a trail along the Housatonic River. It brings to mind another era of tire swings, rafts, and fishing poles. A nostalgia that I did not experience growing up in suburban New Jersey in the 1950s.
We hike out 30 minutes and return 30 to reach our goal of three hours of hiking today.
Weary from the 4A wake up call, traveling four hours to this point, and hiking for three hours, we take country roads back to I-84 and eventually to Mom’s apartment in New Jersey two hours away.
Mom is a pretty sweet journey’s end.