Day One

Wingdale, NY to Kent, CT
May 21, 2017

My wife Anna and I had flown up together for a three-day weekend to the westernmost part of Connecticut. After spending a good deal of time ambling through quaint New England towns (one of which, Kent, we fell in love with), hiking around a few miles up mountains and to picturesque waterfalls, and enjoying beer with strangers in strange places, we parked outside a small suburb in Wingdale, NY off of State Road 55 and walked to a message board which read “Welcome to Connecticut.”

I was eager to begin but a bit nervous. Although I felt my gear was suitable (I had trail-tested it for two days on the Florida Trail and four on the AT in Georgia), I seemed woefully unprepared physically. I weighed 185 pounds, most of which seemed to be poking out between the chest strap of my backpack and my waist; I had done very little in terms of exercise beforehand. I had intended to; but failing that, my thought was that the Trail itself would be my preparation for the Trail.

After a few hugs and kisses and a wave goodbye, off I went into the woods (which was level and surprisingly marshy) into a state with very little of the AT in it (not many more miles than I had walked on my four-day trip in Georgia), with a spring in my step and roughly thirty pounds on my back, which is less than half of what I was carrying in 2003, thanks to Andrew Skurka and fourteen years of technological improvements in hiking gear, in addition to shopping mostly online instead of getting buried by “must-haves” at the local outfitter in town (the weight of which quickly adds up, and which invariably end up being “dont-needs”).

I had incorrectly assumed this state would be a cake walk. To someone who had hiked the Trail since Georgia, it probably was. But to my unseasoned legs, it was a slight shock to the system, despite my prior jaunts in Florida and Georgia in full hiker regalia.

The first mile or so was easy enough. The foliage here contained plants resembling lily pads and cattails. I crossed log bridges over bog on relatively level terrain, verdant and oddly swampy (I hadn’t expected bogs on the New England portion of the Trail). There were portions which almost looked like sidewalk: rectangular wooden rails containing compressed soil and gravel which somewhat resembled a flowerbed. It was unexpectedly pedestrian-friendly. However, I soon began ascending up a mountain out of the marshes into an actual climb, past old stone walls which long ago marked farm boundaries, up into elevation which afforded a beautiful view of the town of Wingdale below.


It was a pleasant enough walk; the trail meandered through beautiful trees, and the weather was positively perfect. But it was the first time I was completely alone in the woods (the first two hikes I had done in Florida and Georgia were with my dog and son, respectively), and it was a bit disquieting. The silence was only punctuated by the occasional sound of distant cars on the nearby roads and my own shuffling.

The trail corridor is quite immersive. Despite the occasional road crossing (or road walk), the sense that you are in a wilderness is pervasive. However, particularly in Connecticut, it is almost always very near highways and indeed entire communities. If I were to have somehow become disoriented and left the trail here, it would have only taken minutes to enter back into civilization. The illusion of isolation is remarkable.

One thing I noticed immediately were the birch trees, which we don’t have in the South and are very evident from their white bark, almost all of which were fallen and rotting. I wondered if they were undergoing some sort of blight similar to the one that took out the American chestnut in the early twentieth century. As it turns out, the trees are “shallow-rooted and vulnerable to being knocked over by strong winds,” according to Jane Wingate in an article in New Hampshire Magazine. Their number would increase as I hiked farther north, but most of the ones I saw were horizontal.

I soon arrived at what locals referred to as The Bridge (as if there were only one in the state). It crossed Tenmile River at its convergence with the Housatonic, which the AT would more or less follow for nearly the rest of its fifty-one miles through Connecticut. The Bridge was actually Ned Anderson Memorial Bridge, a small plaque informed me; but it was made of concrete and steel and decidedly unpicturesque considering the beauty of the surrounding terrain. Its namesake had been a trail blazer and maintainer for the first nineteen years of the Trail’s existence in Connecticut. The trail followed the river for a bit, the happy sound of water splashing against rocks to my right, which was always a cheering sound in the woods, but more so when it’s your only companion.


I continued, down to a short walk along Schaghticoke Road (pronounced Ska’-ti-coke), then on past strewn boulders and over twisted roots, into the only Indian reservation on the entire Appalachian Trail: the Schaghticoke Reservation. Here the trail dipped back into New York for a few miles, and it was slightly beyond this portion of the trail that there had been a fire only a week earlier which consumed hundreds of acres, started by an irresponsible hiker whose unattended campfire had ignited the New York side of the mountain. Even on the morning of my hike there were notices posted of a trail closure, which meant a miles-long road walk to Kent — something I was not looking forward to. Fortunately for me, that very morning the ban was lifted, and I hiked up through the reservation and the burnt section of trail.

If it was weird hiking alone, it was even weirder walking through the charred remains of the forest. At first, the damage was only present on one side of the trail. I had wondered if the firefighters had used the trail as their line of defense against the blaze spreading toward Kent, which was possible; however, it soon became evident that if they had done so, it had not prevented the fire from spreading over the trail to the other side. I was soon walking through the wreckage: blackened remains of trees on both sides of me, surrounded by a gray-and-black ash covering the ground. The trail was the only brown earth visible, determinedly cutting through the ruin surrounding it.

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I was previously warned about coming up here at all by a shopkeeper in Kent, telling me all I would find would be “charred trees and pissed-off rattlesnakes”; but the only snakes I saw were, thankfully, nonpoisonous. One was a beautiful black snake, about five or six feet in length, which slowly slithered across the trail not more than ten feet ahead of me. He was probably looking for a new home, or perhaps returning to it after fleeing the fire.

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I was soon hiking near the town of Kent, which was spread out in the valley just below me in a picturesque vista. Anna and I talked of possibly retiring here. I could envision starting a small brewery/tasting room/hiker hostel just south of where the Trail crossed the highway outside of town (there was a disappointing lack of local breweries in the area). I was certainly already thinking about getting a beer. In my estimation, nearly every hiker would welcome such a business.

Soon I reached Mt. Algo Shelter just north of town, which was to be my stop for the evening. There were already several hikers in the shelter. Three of them, I later learned, were firefighters from nearby Massachusetts who were only hiking the portion of the AT in Connecticut. It was early evening, I was a bit restless, and I truly did want that beer. I mentioned it to the group of firefighters, and one responded with, “A man after my own heart!” So with that encouragement I started for town, but my intention to get a brew took a backseat to my more primary concern: buying a birthday gift for my wife, whose birthday was next month and that I would miss because of my hiking trip.

I stopped in to a small country knick-knack store in which we had been browsing the day before and bought a jigsaw puzzle — then realized it was Sunday and the post office was closed. The shopkeeper told me that the local outfitter a few blocks away took packages, but they were closing in ten minutes. With puzzle in hand I practically ran there (which was a bit awkward in a backpack), making it just in time and throwing a “Kent, Connecticut” car magnet into the box for good measure. I hiked back toward the shelter, satisfied but beer-less.

While in town I had briefly considered eating dinner there, but smelling like a hiker and not wanting to offend the less-befouled clientele, I opted for the more prudent course of eating my provisions as intended at the shelter. Including the road-walk into town, my mileage for the day was approaching sixteen, and I was tired. I quietly set up my brand new tent (the shelter was quite full at this point) and with my homemade stove proceeded to heat water to hydrate my dinner.

My entire hiking menu was carefully planned, with mail drops every two to four days of trail sent to post offices and inns along the way. (I had, in fact, picked one up in Kent a few days before starting my hike.) The packages consisted of dried meals, all in freezer bags, which only required nearly boiling water and a good stir to rehydrate. In hindsight, I would never do this again for a long hike. It costs a small fortune in postage and expensive freeze-dried or dehydrated ingredients, takes days to prepare, and is a complete hassle. There are a lot of places to resupply in towns all along or near the trail until nearly the end in Maine, and most people just resupply that way. The idea of mail drops appealed to me because I didn’t have to try to get a ride into town and worry about shopping for things that would last on the trail and didn’t weigh a ton. However, the cost and effort of preparing everything ahead of time was not worth the convenience, in my opinion.

After briefly socializing with the group of firefighters, I changed into my non-sweat-soaked sleeping clothes and climbed into bed with the first book in the Harry Potter series (the rest of which were included in my mail drops at intervals approximating when I would finish the previous book) and enjoyed my first night on the trail in New England.