Day 104, 13.1 miles to Kent

There were two steep morning climbs and then a raging river through a rocky canyon. What a wonderful change of scenery! The trail followed the river until it met the larger Housatonic River, with a footbridge across the smaller one. Then I walked upstream through the bigger canyon, as the Housatonic spun and seethed.

Eventually, I reached the private Kent School campus and cut across their beautiful property and into the town of Kent. Kent is exactly what you expect Connecticut to be, beautiful old houses and quiet inn-lined streets with cheese and wine shops. We had an Airbnb above the ice cream parlor and went immediately out to eat lunch and get iced coffee. At the beginning, I was walking from meal to meal, but now I’m essentially walking from iced coffee to iced coffee. Kent had all the things we needed to do our chores plus absolutely amazing food, the best food so far on trail. Tex treated everyone to dinner at Kingsley Tavern, which was an amazing meal.

July 16 zero miles, Kent, Connecticut

A zero day isn’t very interesting, just lots of laziness and chores. Kent was a great town for a hiker zero, except maybe a little expensive.

July 17, 19.6 miles to Sharon Mountain Camp

Restaurants in Kent didn’t open until seven, so I cooked up eggs, cheese, and toast the last renters left for a good breakfast. Then I rushed out of there early, while the guys were packing up. The trail followed the Housatonic River for most of the morning. It was an especially buggy area, but occasionally there was a muddy beach with a breeze to escape the mosquitoes. Then the trail climbed up onto a ridge and did the usual hot PUDs. The down’s were to reach water, but the ups felt entirely pointless. The only positives out of these climbs were cell service and a breeze. The views were the same old views.

We had talked about stopping at the Pine Swamp Brook Shelter, but it sounded like a beaver pond may have swallowed the creek there. I decided to walk another 2.4 miles to the Sharon Mountain Camp for better water. No one else was there, but it was a multi-site camp with privy, bear box, and cell service. The mosquitoes liked it too. It turned out to be the best choice; the shelter water was horrible and the goofs started the next day dehydrated.

Day 105, 17.8 miles to Riga Shelter

I woke to bloody carnage on my sleeping pad. Apparently, mosquitoes got in my tent when I got up to pee, and I squashed them as I rolled around. I slept through the battle, but my sleeping pad needed a good scrub. The morning had a quick hike down to Falls Village, Connecticut, where I picked up a package. The cafe served avocado toast and oat milk lattes, which weren’t especially good, but at least what I desired. We are no longer mired in the land of pork gravy and white bread. In the afternoon, I passed a beautiful waterfall and climbed gentle Mt. Prospect. The trail dropped back to the road to Salisbury, which I skipped, despite certainty that they would have vegan lattes. I continued up the trail to the Lion’s Head rock viewpoint. The sameness of the views, persisting for 1500 miles, had me yawning, but I assured the proud Connecticut hikers that it was lovely. Most definitely it was—compared to Pennsylvania—so I was truthful.

We stopped for the night at Riga Shelter, a newer log shelter with a view and a breeze, which made dinner at the picnic table possible. Everyone made it to Riga, even Klondike, who had to walk over twenty-five miles after falling behind the day before from foot pain. The water was clear, cold, and tasty, unlike the prior shelter. Both Bluey and Klondike had gone to Salisbury and found it to be pretentious and not hiker-friendly. I still had some regrets, as I was running low on food, but a section hiker offered me extras, without me even needing to hint.

The day felt like a total win, from the cooler weather, charming Falls Village, the waterfall, the pleasant hiking, the breeze, and the company. The heat has destroyed me lately and this day I felt powerful, a wonderful switch.

Day 106, to 18 miles to Great Barrington, Massachusetts 

Today had three steep climbs, getting progressively harder, and I left at six to knock them out before the heat. The first was the high point in Connecticut, Bear Mountain, with a rocky monument. The far side descended into Sages Ravine, a bubbly creek spilling down the hillside. Three signs over a half mile announced our arrival in Massachusetts, as if there was disagreement over the border between the states.

On a gentle slope heading up Mt. Race, I caught my rear shoe on a rock, and unable to disengage, I hit the dirt. I had slipped in mud in Virginia, but this was my first real fall. How ironic, to hop, clamber, and stride across so many rocks and be annihilated by a diminutive stone of zero consequence. I was unhurt, but I hit three points hard, my knee, a thigh muscle, and my titanium-enhanced wrist. It was a “this will hurt more tomorrow” kind of fall, but babysitting that knee slowed me down.

The top of Mt. Race had a series of ledges with sharp drops of 50-100 feet, so I chose the right place to wipe out. Always fall going uphill, remember that. The remainder of the day involved treacherous angled slabs, wooden steps bolted onto the wood, and deadly drops. Mt. Everett was ridiculously steep and baked in the sun. We bunched up on a slab on the down climb from Everett, enjoying the view and breeze. Two section hikers climbed up and one, maybe unnerved by the exposure or audience, struggled awkwardly off route and nearly fell fifty feet into the forest. Taxman said he wasn’t expecting death to be in the plans for today. I thought again of the trail family who did Trail Magic to honor their friend who tumbled off McAffee’s Knob. No more falls, please.

We climbed off Everett to a grassy field alongside the road and began the arduous job to summon a ride. After Lyft, Uber, and the shuttles dashed our hopes, a trail angel drove over, stuffing all six of us in a RAV 4, not even charging for that clown-car ride to the Recreation Center in Great Barrington. The rec center generously allows camping in a grassy field, and for eight dollars, we got morning showers. There were several trail families camped there and a festival of little tents, with skunks skulking around, looking for snacks.

We set up and headed to the packed brewery, sitting outside under an umbrella. The long wait for our food, long day, heat, and bench seats wore me down. I was too tired to eat when the food came. Instead, I packed it up to go and took it to my tent for breakfast. This is not the ideal scenario when camping in a skunk infested field, having a warm container of brisket and macaroni wafting scents across the field. My tent was immediately investigated; then I slipped dinner and my other food into my odor-proof food bag, zipped it shut, and buried it in dirty socks and clothes. No more skunks, just a peaceful night of fireflies. Yay odor-proof Opsaks!

Day 107, zero miles, Great Barrington, Massachusetts 

Our trail angel shuttled everyone else in the morning, and then through some miscommunication, failed to come back for us, the last group. It honestly was a small blessing, as most of us didn’t feel well. There was fatigue or intestinal distress all around, and it was a hot day with a big climb to iffy water. We decided to use Flora’s trick to see what we really wanted from the day. Flip a coin, she suggested, and see how it lands. You don’t have to do what the coin tells you, but if you’re disappointed by how it falls, you’ll know what’s true to your heart. We had no coins, so Taxman took a Zins tin, assigned “hike” and “zero,” and gave it a flip. The tin flew up in the air and bounced across the floor, landing on its side, rolling, and never tipping to heads or tails. He picked it up again and tossed, getting the same result. Even the universe was unsure what to do with us today. In the end, we couldn’t get a shuttle to the trail and that decided it.

PMA’s girlfriend came to meet him and helped shuttle us downtown. Hotels had opened up, so we ate lunch in Great Barrington and headed to our rooms. I had wanted to go to college in this town, at a high school/college blend, Simon’s Rock at Bard College. My parents swatted down that dream, with two already in school. It was a chance to imagine an alternate me, who lined up funding alongside admission. I prefer Oregon me.

We dropped packs at the hotel and walked to the outfitters together. I walked behind Alyssa, who smelled amazing and wore a pretty dress, trying to stay downwind of her. The outfitter stocked some of the clothes in my wardrobe, making me miss clothing options more than ever. It’s hard to wear the same stinky outfit daily and watch tourists roll their eyes at our stench.

For some reason, any zero day causes my legs to ache, as if hiking is now necessary just to feel normal, but this post-wipeout day was especially painful. I hurt all over and felt slightly feverish. I bought some hippie comfort food at the Berkshire Co-op and crawled into bed with kimbap and matcha mochi.

Day 108, to 17.6 miles to Shaker Campground 

The hike started in farmland, along the edge of a tall cornfield. Yellow jackets struck first thing in the morning; Klondike shrieked in pain, swatting at his neck, dropping his hat, and dashing off. Before we realized what was happening, another stung Tex behind his ear. He dropped both trekking poles and ran back towards me and Bluey. Now we were split, with three behind the wasps, around a corner, out of sight of the others. We let them simmer down and Tex sprinted through, recovering the gear unscathed. Bluey and I waited and dashed past.

There was a climb up to a rock slab, and of course everyone bunched up there, enjoying the flat rock, cell service, and view. Slab slackers, that’s what we’ve become. I headed on to ponds and swampy areas, with a beaver lodge and a beefy bear cub. The restricted camping limited our choices, so we stopped at the official Shaker campsite, the location of a religious colony in the 1800’s. A smoky campfire chased off the mosquitoes for dinner at the picnic table. The guys placed bets on Klondike’s arrival, which never happened. He was meeting his family in the morning and wasn’t worried about keeping up. The camping was tight but comfy, a good evening.

Day 109, 21.1 to the Cookie Lady’s

A quick climb in the morning got me over Cobble Hill and down to the AT Stand, an iconic trail magic fixture. The AT Stand is a small honor farm stand selling fresh eggs to locals and treats to hikers. I bought a cold chocolate milk, made myself a mocha, and sat at the picnic table eating snacks, enjoying WiFi and a charging station as my dewy shoes dried in the sun.

I climbed over Baldy Mountain and passed a number of inaccessible pretty lakes and ponds. While lakes are a novel treat, I appreciate them more if I can at least sit on the shore or dip in my feet; I could barely see most through the trees. The trail went across the Massachusetts Turnpike on a pair of pedestrian bridges and then straight up Becket Mountain to no view, just a tangle of invasive vines. I had one more steep PUD to the shelter where we planned to meet. The shelter water was a disappointing brown stream that would challenge my filter, but I grabbed a quart and hiked up to find a pair of squabbling section hikers whose tent filled the entire shelter (not cool). “Are you looking for Bluey and Text?” one asked. “They went to the Cookie Lady’s, they asked us to tell you.” Then they had an argument over whether he was Text or Tex, without thinking to ask me, although I was happy to be left out of the battle. I didn’t feel like walking two more miles, but they were a good incentive.

The Cookie Lady offers camping on her blueberry farm, with work-to-eat options. We did not spend our last hours of daylight picking berries; Tex called in a Five Guys burger delivery and we feasted. A section hiker sat with us, waiting for dinner to end so we could shake him down. A shakedown is when experienced hikers sort the gear of a newbie to lighten the load. We nixed his hatchet, moccasins (he also carried Crocs), a massive first aid kit, a large pot, most of his mess kit, a cotton hoodie, extra clothes, three heavy water bottles, a thick rope, a bottle of Crisco, another of Dawn, an extra flashlight, rain pants, and a full roll of duct tape. We suggested the standard rule, that if you haven’t used something in the days you’ve already been on trail, then send it home. So he tossed out his roll of TP and we all yelled in unison, “No! Keep that!” It’s unusual that the privies have had TP lately. He put on his emptier pack and was so happy, except that he still had to carry the discards to Dalton, ten miles away, to mail home.

Day 110, to Father Tom’s camp in Cheshire 

We punched out two big climbs in the morning and dropped down to Dalton, heading straight for iced coffee and then next door to a sub shop. Dalton was baking hot, enough to make me dizzy. We needed a resupply and another nine mile hike to Cheshire, but my heat-avoidance radar snapped to alert and hit full DEFCON 1. This could be bad. Using Apple Maps, I came up with an alternative, a forested road walk to Target, followed by a rails-to-trails route along a lake all the way to Cheshire. I thought I was going to be on my own, but everyone was onboard with the breezy lake hike and we headed off together.

Cheshire was another charming trail town, with an ice cream stand by the community hiker camp. This was my favorite town camp so far, with a soft lawn, trash, charging, water, and porta potties. Bluey rode a loaner bike to the gas station for cold beverages and we sat around, listening to the Lewis Brothers, Bluey’s musical past, enjoying the ironic “I lied about being outdoorsy.” It was a good day.

Day 111, 19 miles to small stream on Pine Cobble

Today was all about Mount Greylock, the high point of Massachusetts. I said goodbye to the comforting Cheshire campground and headed up early, to beat the heat. Eight miles is a long way to go uphill, especially with a steep section at the beginning, but I found the climb was better than I expected. At the top was a large monument and a lodge. I chose the lodge; monuments don’t have iced coffee. FarOut (our navigational app) warned of a grumpy lodge-keeper with grey dreadlocks, but he kindly led me to the closed kitchen and ordered up my coffee. I cooled off, luxuriating in the lofty view. The Goofs and other thru-hikers showed up, including friends from a slack-packing crew with a hiker whose badly injured shoulder can’t wear a pack and another in the Urgent Care with possible Lyme’s disease. 

What goes up must come down, including hikers. We passed a suffering Scout troop, complaining loudly as they neared the top. I could relate. The trail wound down endless and steamy, until we stopped on a slab and enjoyed a break. It seems to be a pattern, us sitting on slabs, looking at the town below, wishing to already be there.

Klondike texted he was back on trail ahead of us. He found trail magic along the road and that got us moving. Williamstown was baking hot, and everyone collapsed at a kiosk with coolers, generously offering cold water, drinks, and snacks. They even had a box with first aid and hygiene supplies. It was hard to leave the shade and coolers for a five mile hike, mostly uphill, in 88 degrees. I texted a trail angel who allows camping in her yard, but I didn’t hear back until I was a mile uphill from her house, probably for the best. The climb was cooler than I expected, but quite difficult at the top. After wasting so much time lying in the grass, it was almost eight when I rolled into camp. A trail crew was using half the camp to store stuff  and the rest of the sites were full of Goofs; while it isn’t ok to camp on the trail, it seemed perfectly acceptable to camp on the trail within our campsite. Good thing I have the tiniest of tents, as it was the only flat space left. I peeled off my sweat-soaked clothes and crawled sticky into bed, exhausted.

Day 112, 12 miles to Bennington Vermont

I woke at 5:15 to find a deer fly inside my tent, as full as a thru-hiker at the Chinese buffet. It couldn’t even flee, it was so stuffed with my blood, and my feet and hands were speckled with red welts. Getting into camp late is hard; getting started early afterward is harder. I wanted so badly to doze back off, but there was a plan to reach twelve miles to Harmon Hill by 1:00 and I needed to hustle. I knew how to not doze off again—let the air out of my sleeping pad, so it’s too uncomfortable to lay there any longer. Once I can’t sleep, I might as well hike, and so I did, reluctantly. It was already hot or still hot, however you frame it. Remember that feeling of pulling on a wet swimsuit when you were a kid? That’s what putting on my hiking clothes felt like, only without the fresh chlorine smell. 

After a couple of miles, I reached a cut in the forest where power lines ran and a cool breeze blew across me. Heaven. Here I was on the Appalachian Trail, on a section that is also the Long Trail—one of the oldest and most celebrated trails in America—and I was miserable. Hike your own hike, they say, but was I? Did I want to hustle all day in the heat, chasing that 1:00 goal, just to head down a two-mile rocky descent that people reported was sketchy as hell in the rain, and it was supposed to rain? What was I doing? Why was I here and what kept me here despite not enjoying myself?

Well, I like to finish what I start, and I hate regrets. I didn’t want this to become one. In all honesty, completion is the main reason I’m still here. Vermont, I reminded myself, is someplace I always wanted to see. I reached a rough dirt road, checked my app, and took a hard left downhill. Let’s go see Vermont, I thought, and get out of this green tunnel. It won’t be the first time I walk off trail and it won’t be the last, as I walk to Maine. I headed steeply downhill and into an off-grid backwoods community, haggard at first, with tired trailers and rusted cars, growing more prosperous, with solar panels and fruit trees. I reached the power lines before the pavement, and classic white farmhouses decked in flowers, with big red barns and mowed fields. Subarus passed me, slowing to wave or ask if I needed a ride. I felt like if I knocked on a door, Bernie might open up wearing hand-knit mittens. I was so happy finally.

A border collie ran out after me, herding me like a cow, and her person Steve invited me over to take a flier for his hiker festival on Saturday. They still had free rooms for hikers reserved at the hotel, he said, and helped me book one. After filling my water bottle, he offered me a ride. I reluctantly declined and I hiked on. My legs began to ache and there was nowhere to take a break. I tried sitting by a fish hatchery with a pond of rainbow trout, but the workers ran around frantically, chasing some creature, shooting at it with a rifle. It was not relaxing. I sat at the fire station, but the good Vermonters stopped their Subarus to see if I needed help, also not relaxing. So I kept going, proud of my resolve, when Steve drove up with Tex in his truck and I jumped in for the last couple miles, my remaining shreds of pride be damned.

Bennington was lovely, and we dove in. Iced matcha and an eclair, followed by a short walk to hot coffee and avocado toast with sunside-up eggs in balsamic drizzle. New zero-day shoes for Tex at the Dollar General (pink slides) plus the last treasure of a chicken packet in the store for me, and finally collapsing at the hotel, a hiker-friendly dream.

Klondike appeared, slumping to the floor after hiking 17 miles on a longer route to town, and then the purists arrived from the trail by shuttle. Everyone got what they needed from the day, and by coincidence, our rooms connected like a suite. The showering and feasting and relaxing commenced.