Graymoor Monastery through Connecticut: Hiking the Appalachian Trail

Over the past few months, I’ve been going through my journals and old maps and recalling the summer of 1987, when I hiked 1300 miles along the Appalachian Trail. Between 1983 and 1988, I hiked the entire 2100 miles of the trail. This section takes us from the Graymoor Monastery on the north banks of the Hudson River through Western Connecticut.


Father Brosco at Graymoor.
The day starts early at Graymoor. I wake up in the predawn hours and read from the Bible on the table by my bed. In my pack I only carry a copy of the Psalms and New Testament, so it's a treat to read from the Old Testament and go searching for a verse I’d remembered. After a bit of thumbing around I find it.

"The land shall not be sold for ever: for the land is mine; for ye are strangers and sojourners with me." -Leviticus 25:23

Although I’d been on the trail for five weeks, I still had not adopted a nickname with which I was comfortable. Slim Jim and Daddy Long-legs tried to get me to use “Dental Floss” as I had a habit of flossing while leaving camp in the morning, plus I’d used floss to sew up my boots and pack. But I didn’t feel the name fit. I’d been thinking about “Sojourner,“ a named confirmed after finding this passage. After reading for a few minutes, I go into the bathroom where I noticed there's a scale. I step on it and am shocked to realize that I weigh 164 pounds, less than I weighed when I graduated from high school. It's no wonder I'm hungry all the time!

I have breakfast with Doug (AT Believer) and Father Brosco and afterwards the three of us attend morning mass. I'm surprised when Father Brosco invite us both up to take communion. Not being Catholic, I politely declined and remain in my pew while Doug, an Episcopalian I believe, go forward. Afterwards, Doug and I take off in the misty rain. We spend the morning hiking together, talking about our experience at Graymoor. In a strange way, I feel God’s presence back in my life. I tell him about my new name, “Sojourner,” and he affirms that the name fits. We also talked about the monks at Graymoor and how hospitable they were to a bunch of dirty hikers and how they seemed to relish at the opportunity to answer our questions. However, upon further reflection, I find myself wondering if they enjoyed the dialogue as a way to learn or just as a way to dish out rote answers. Cynicism seems to be a personal demon attached to torment me, as it always seems to make its way into my thoughts, even after having such an incredible experience.

After lunch, Doug goes on ahead. I'd been slowing him down as my left thigh is numb and tingling. I was hoping my planned hike of nearly 20 miles would free it up, yet didn't want to hike too fast. Shortly after lunch, the skies open, but the temperature is warm. I’m hiking in just a t-shirt and nylon running shorts and my pack s dry under a rain cover. I kept pushing on, marveling at the beauty of New York State. Much of this area had been covered with glaciers in the last ice age and there are signs all along, of bedrock smooth by the grinding ice, mountaintops flattened and large boulders left behind. As I hike, I notice that the most common sign along this part of the trail reads “No Trespassing.” I think back to the verse I’d read early this morning and shake my head.

A part of the trail, just south of NY 301, is along an old narrow gauge railroad bed built during the Civil War to haul iron ore out of these hills in order to turn it into cannon balls to lob at my ancestors. I'm amazed a train could make the grade, but it's former path makes for good walking. I arrive at Ralph’s Peak Hikers Cabin at 6 PM. Doug's there along with two boys hiking together and a guy who goes by the name “Winds the Winowalker, whom I’d been reading about in trail registers since Maryland, where he’d started his hike on June 6. He’s living in Boston, but is also from North Carolina. The cabin is a wonderful place to spend a night that consists of one downpour after another. The rain on the roof provides music for sleeping and drowns out any snoring.

It was still misty the next morning, July 8, when I leave Ralph’s Cabin. Although I can’t think of anything I'd more want to do, it's hard to get motivated to hike after the rain. In my mind, I know I must to average 15 miles a day to reach Katadhin in time to get back to North Carolina and retrieve my car and then get back to Pittsburgh for school. But I fiddle around, taking my time to get going and don’t hit the trail till 8 AM, an hour after Doug. We never see each other again, but I kept up with him in the shelter registers. He'll climb Katadhin a few days before me.

I hiked almost ten miles in the morning, stopping at noon at the Morgan Stewart Shelter for a long lunch. An hour later, the Winowalker comes in and I stay around and talk to him for another hour before heading out. Although I'm clicking off the miles, the day's boring, the main highlight being the infamous hike around the fence-off “nuclear” lake. The trail has been detoured around a former nuclear test site where, supposedly, there's unaccounted plutonium. Luckily I don’t find any, but I wouldn’t have wanted to have carried anything that heavy if I had found some. My left thigh is still bothering me and the pain extends down into that knee. For the first time, I pulled out a small AM/FM radio that Shari had left with me when she got off the trail, thinking to myself I might as well listen to “the bearer of bad news” as a distraction. I hope to find out when the weather was going to clear, but instead catch up on Oliver North’s testimony in the Senate hearings on the Iran/Contra Affair. Later, I change to a music station and laugh when “Walking and Rhythm,” is the first song heard. Later, they play “Don’t Fall in Love with a Dreamer,” a song I figure any woman interested in me should listen to at least daily.

I'm making pretty good time and click off another ten miles in the afternoon, when I come across a country restaurant along NY 22. I stopped for dinner and it's late when I got back on the trail, with less than an hour of daylight left. The trail has been following the side of roads and cutting through pastures and there had been no place to camp for several miles when it enters the Pawling Nature Preserve. A sign indicated that camping is prohibited for the next three miles. As there was no place to camp behind me, I head on, figuring that instead of camping, I’d find a hidden spot to lay out my bivy sack and to drop the tarp over me in order to spend the night. As I enter the woods, fireflies are coming out as are the mosquitoes and deer flies. I walk till dark, find a level spot hidden from the trail, spread out my bivy and sleeping bag and drop my tarp over me and am soon asleep.

I get up the next morning and am back on the trail in a hurry, starting to hike at 6:30 AM. Shortly after leaving the nature preserve, I take an early break at the Gates of Heaven cemetery, which must have been primarily an older Jewish cemetery considering all the Hebrew markings and symbols on the tombstones. The most recent graves I see are dated from the 30s and 40s. I continue on and stop for breakfast at Wiley Shelter. Reading the shelter log, I noticed I must be only a day behind the Brits and gaining on them. I laugh at their entry. They had clipped an ad from a newspaper for a revival at a Baptist Church that reads, “Smile America, God Loves You.” They’d “glued” the clipping into the notebook with chewing gum and underneath had added the slogan: “But He prefers the British.” I take my time in the morning, reading the last of Nouwen’s book. I like what he says toward the end, "a monastery is not built to solve problems but to praise the Lord in the midst of them.”

Near where I have lunch, at the Dogwood Corner, where the trail enters Connecticut, I'm shocked to discover someone had painted the letters KKK on a utility pole. I’d seen only one other such sign along the trail, in New Jersey, where someone had carved the letters into the white trail blaze. I hike a little over 17 miles, passing the Mt. Alto Lean-to and then walking half a mile down Schaghicoke Road into Kent, Connecticut, arriving right before the Post Office closed. There's a package from Shari with copies of John Steinbeck’s Travels with Charlie and William Least-heat Moon’s Blue Highways and homemade oatmeal cookies. There are no other letters, but I figured that other mail probably went to the Cornwall Bridge and I’d be there in less than two days. I find the cobbler, but he's closed, so I grab a hamburger for dinner and read Shari’s letter and write a few of my own. She tells me about going with her brother down to the coast for a few days and then having to go home and call her friends who’d expected her to be gone all summer. “Bowser,“ she said, “has been fine since arriving back in civilization”. After dinner, I head back to the trail. A truck pulls up and a guy suggest I hop into the back, that he’d give me a ride to the trail. When he lets me out, he invites me to have dinner with him and his wife, but I declined, telling him I’d already eaten. I walk back up to the hill to the shelter.

Ben hiking in Connecticut

There's one other hiker at the shelter when I arrived, although he didn’t look like a hiker. He's wearing trousers and reminds me of the mysterious man at the shelter just south of Lehigh Gap, Pennsylvania. At Lehigh Gap, I was with Slim Jim and Daddy Long-legs, now I am alone and the man gave all indications he wants to be left alone, so I don’t say much. I prepare my bed, rolling out my ultra light pad and inflating it and fluffing out my sleeping bag. After reading a bit of Steinbeck, I crashed for the night.

I headed back into town the next morning and drop my boots off at “The Kent Cobbler.” The cobbler is a nice man named Len. I told him about the pain in my legs, and he suggests I try a pair of inserts with higher arch supports. While he's working on my boots, I stop at a drug store and pick up some new inserts and then do some grocery shopping and am shocked at the prices. I pack the food and head to the post office to mail letters and to send a box of stuff, including the Blue Highways book and extra food, on ahead. I have lunch with a southbound hiker from Great Barrington and we joke about how preppy the town is along with how cute the girls are. It's right at noon when I pick up my boots and head back toward the trail. It's 92 degrees and as I walked along the side of the road without any shade, I feel the heat.


Hikers along the trail in Connecticut can only camp at shelters or in designated campsites. I hike on through the afternoon heat, my left leg and knee still hurting despite the new inserts. I cover only seven miles of trail (not counting hiking in and out of Kent), stopping for the night at 4:30 PM at Steward Hollow Campsite. I'm surprised to see the same guy here who'd stayed at the shelter the night before. First impressions can be wrong. His name is Ben and we became good friends, hiking together for the next week and keeping up with each other for many years after completing the trail. I set up my tarp and then take swim in the Housatonic River.

I leave camp early on the morning of July 11, hoping to beat the heat. It's beautiful hiking along the river in the early dawn, the sun’s rays breaking through the trees and burning away the dawn. Unfortunately, my camera is stashed in my pack when four deer break out of the woods in front of me and crash through the river, the splashing water that creates prism colored droplets, one of the most beautiful sights I’d seen. By mid-morning I'm at Cornwall Bridge. I stop for a Danish and coffee at the bakery on the edge of town, then walk over to the Post Office. There are no letters from Debbie, but there is mail that Eric had sent me from school and a package from my parents. There was also a letter from another friend who’d once talked about joining me in Vermont. He's unable to make it, and I am both sad and glad. I’d resigned myself to hiking alone and was okay with that and also knew that it would take a few weeks for someone new to catch up with my speed on the trail.

I take care of the bills Eric forwarded and go through my parents package. I‘d stashed a number of mailers for slide development, so I send off the exposed film off to Kodak. There's another book that I‘d put in the package, Herman Hesse’s Narcissus and Goldman. There's also a cigar in the package from my brother, who's celebrating his daughter’s birth. I realized that today is also his birthday. My mom, who always collected stationary from every hotel she stays in, has written a letter on thin rice paper stationary from the Palace Hotel in Tokyo. She mostly tells me about her beautiful and wonderful her new granddaughter (my niece) and admonishes me to be careful.

As I was taking care of business at the Post Office, I'm approached by a guy named Richard who owns the Package Store next door. He invites me to stop by and see him before leaving town, which I do rather reluctantly. He’s just opening up for the day and tells me that he likes to treat hikers to a beer and that I could have anything that he sells. As it’s still early in the day, I suggest I pass but he encourages me to take one for later in the day, suggesting that I could chill it in a stream. I ask him what he recommends and he suggests a Foster’s Lager from Australia. It was my first experience with this beer which comes in a 25 ounce “oil can.” I thank him and put the beer in the top of my pack. After Cornwall Bridge, the trail leaves the river valley and climbs steeply up a hill through Dark Entry and Cathedral Woods. The leafy canopy is tight and blocks the intense sun, but its still hot and humid and by the time I reach the top of the mountain, I’m sweating like a dog. I shed my pack and reach for a water bottle when I feel the can of beer, still cold. “Why not,” I think. Even though it’s not yet lunch time and I’m pretty dehydrated, I go ahead and enjoy the beer, the cold liquid tasting great as it goes down my parched throat. But the beer also goes to my head and I’m lightheaded as I make my way down the mountain. I stop at a stream and find a nice place with plenty of soft needles and take a nap through the heat of the afternoon. Later, I walk on to Red Mountain Shelter where I camp with Ben and Bill, a guy out for the weekend.

Housatonic River

The skies are clear and it promises to be a great night to enjoy the stars, so I camp outside, under the stars, in my bivy sack. As soon as the insect repellant wears off, I’m attacked again by mosquitoes. As my bivy has no screen and its so warm that I don’t need a sleeping bag, I stuff my bag at the top of my bivy to block the opening and try to sleep down inside the bag. But it’s off no use. I get up and put on more repellent and that gives me another few hours of sleep, but then bugs return. I’m up again at 4 AM and get out the cigar my brother sent me and smoke it, hoping to deter the mosquitoes. I hear Ben rustling in the shelter and he too is cussing the mosquitoes. He packs up and in the dark, hikes off. An hour or so later, when the stars have just begun to fade, I join him. This turns out to be my worst night on the trail.

The morning air is muggy and very still. I’m quickly sweating. By late morning, I catch up with Ben and we have lunch at the Village Diner in Falls Village, CT. It’s a fairly easy hiking day with the exception of Barrack Mountain which is steep. Ben suggests that it's my preview of the White Mountains. I find myself musing about what we eat on the trail (nuts, crackers and cheese, M&Ms, and smoked sausages) is often served at parties and I wonder if I’ll be tired of them by the time I return to civilization. We do an 18 mile day (a long day for Ben), stopping for the night at Limestone Springs Lean-to. It’s my last night in Connecticut.

Other posts on my 1987 hikes

Hiking the Berkshires (the hike after this one, I wrote this in 2007)

Delaware Water Gap to the Hudson River (the hike before this one)

Duncannon to Delaware Water Gap, PA

Duncannon, PA

Maryland and Southern PA

Northern Virginia