A day when I get to head into town is always good, and I set off along the trail already thinking about my town chores and real food. Even though the eight miles into town looked like they were mostly downhill, the rocky trail still went over multiple small uphills that were too small to register on the elevation map, but still made my legs burn and slowed me down more than I wanted. I grumbled at the trail angrily every time I saw it take an uphill turn, having mentally only prepared myself for eight easy downhill miles. I finally made it down off of the ridge and into a swampy area of trail with small board walks.
Here I could finally keep up a good pace, and it’s good that I could, because mosquitoes started flocking to me the second I would slow down despite the copious squirts of bug spray I applied. I raced through the swamp and finally came out onto the road, where after 15 minutes of trying to hitch I got a ride. This is the second hitch I’ve had where I’ve gotten to sit in the bed of a pick up truck, and it was just as enjoyable as the first one. Getting 360 degree views of the country side and town while enjoying a nice breeze is just a great way to ride into town. Right as I was getting out of the truck, the guy who had given me the ride gave me a bottle of fancy lemongrass essential oil bug spray, which was some very nice and needed trail magic since my bug spray was almost empty. I stopped by the post office to pick up a new pair of trail runners, as I’d been wearing my current pair for over 800 miles. The new pair felt like walking on a little cloud, since the cushion in my old pair had long since been reduced to pancake flatness. I grabbed a quick lunch, a chicken quesadilla that I’d been craving on the trail for days, before I did my resupply and headed to the hotel. The hotel was great, the shower was much needed, and I spent the rest of the evening relaxing in my room.
I relaxed for most of the morning before finally setting out and getting a ride back to the trail. The climb out of town was long but not too strenuous, and soon I was headed back down the gently sloping hill. There were plenty of small trickling water sources and some interesting large boulders along the trail, but the trail was mostly wooded rocky slopes without anything super interesting, so eventually I put on a couple podcasts to help pass the time. The end of the day involved a series of small ups and downs that led progressively higher. On the first one of these a day hiker’s dog wandered up to me and I got to enjoy petting her and telling her how cute she was for a minute before her owner caught up. Towards the top of the long hill I passed a couple small ponds which were nice and quiet, but I didn’t linger due to the mosquitoes.
I made it to the North Mount Wilcox Shelter a little early, but it was supposed to rain overnight so I headed in. There were a bunch of hikers already there, although none I recognized, and I managed to squeeze into the back of the shelter for the night.
I set out early from the shelter and started the ups and downs of the day. The first downhill led to nearby pastures some of which had cows in them, and a large boardwalk over a grassy bog.
The mosquitoes were on the attack pretty quickly, and despite its nice lemony smell, my trail magic bug spray didn’t seem to be dissuading them much, so I had to spray a lot of it on and keep moving quickly. After a quick climb and some rolling hills the trail came to the edge of upper goose pond, and I picked a nice rock on the breezy site to have lunch on. Fortunately the breeze kept the bugs at bay, and I hung out by the shore for a while before continuing on. After crossing the mass turnpike on a bridge the trail turned uphill again and started a steep climb up Beckett Mountain. I took my time heading up, and frequently stopped to poke and talk to the efts and toads also using the trail. After reaching the summit the trail thankfully flattened out a bit, and I cruised along until I reached the October Mountain shelter, my home for the night. There was a mix of thru hikers, section hikers, and weekend campers at the shelter, and we chatted over dinner before I crawled into my quilt. The mosquitoes were still pretty aggressive in the shelter, so I sprayed on a little more bug repellent more calling it a night.
The morning passed quickly on some relatively flat terrain for the first few miles, and I was happy to walk through open spruce forests and over numerous planks covering the muddy ground. The climb up Warner Hill was pretty easy and I started heading down the hill on a trail through the ferns when after a couple minutes the trail I was on petered out, I’d managed to get off the AT on the summit somehow. I pulled out my phone and looked at the map while bushwhacking sideways through the high ferns until I made it back to the trail again, whoops. The trail continued down towards Dalton, where it connected to some roads and led into town. In town I stopped by a coffee shop for a smoothie and breakfast burrito, and enjoyed sitting outside while eating. The weather has been really nice the last few days, in the mid to high seventies and only raining a bit overnight, which is unusual for the Appalachians, and I’m definitely enjoying it while it lasts. After lunch I started up again over what looked like a relatively normal hill, just around 1000 ft of elevation gain, so not very high compared to some of the other mountains recently. Unfortunately, my feet didn’t get the message that this hill wasn’t actually that hard, and they started feeling really sore and tired pretty quickly after starting up the hill. I continued on as quickly as I could manage on my sore feet, pausing at a small pond and some nice water sources to take a breather. Finally I crested the hill and started downwards, my only goal to make it to the camp site as soon as possible. I made my way into the town of Cheshire and into the town hosted Father Tom campsite, where I immediately dropped my pack and laid down on the soft grass to rest for a few minutes before setting up my tent. The campsite was fancy, with a water pump, privy, charging station, and bikes to borrow to head into town. Even better, there were no mosquitoes! After resting for a bit I cooked up some chili for dinner, and talked to the other hikers while eating. I was feeling pretty exhausted and headed back to my tent after eating, very eager to give my feet a break and lie down for the night.
I discovered the one drawback to the Father Tom campsite overnight: by being in a low field surrounded by trees blocking the breezes there was a lot of condensation, and I packed up a pretty damp tent in the morning. I got on the trail by 7 am, and pointed myself uphill towards Mount Greylock, the highest point in Massachusetts. Despite the cool morning I started dripping sweat almost immediately upon starting up the very steep hill, and I took numerous breaks as I slowly climbed above town, onto the ridge, and up toward the summit. Toward the top the forest changed from mixed hardwood to mostly firs which smelled like Christmas trees. Before the final push to the summit the trail passed a small pond with an old cabin on its edge, and I admired the pretty scene and the clear reflection of the cabin on the pond’s surface.
Finally, four hours after getting started in the morning, I made it to the viewing tower at the summit of the mountain. I took in the views and grabbed a seat on a bench so I could make an early lunch.
On the grass right before the large view a bunch of paragliders we’re setting up their gear, and a crowd of people gathered to watch them prepare to jump off of the cliff nearby. Unfortunately the wind was blowing the wrong direction, so they stowed their gear for a while, and I eventually packed up and continued on. The descent off of the mountain was just as long and steep as the ascent had been, and it was a long time before I started hearing the sounds of the town below. The trail popped out again on a road in town, and I quickly made my way down the streets, noticing how hot the temperature was at the lower elevation and without the cover of trees. After crossing town and heading back into the woods, I took a quick break by a stream to give my feet a rest, before continuing on. Another climb faced me, and although it wasn’t as long as the climb up Mount Greylock, there was one extremely steep rock scramble that looked like it was going almost straight up. I hauled myself over the boulders until the trail finally flattened out again. At this point I was feeling super tired from the big climbs, but the shelter was still over four miles away, so I trudged on. Just a few minutes later I passed the 1600 mile marker on the ground, and ten minutes after that I crossed into Vermont, two very exciting milestones to end the day with.
The last little hill of the day felt twice as long as it really was, and I was so glad to finally spot the sign for the shelter, a full twelve hours after I’d started hiking that morning. I threw up my still damp tent, and made a quick dinner while talking to the other hikers there, before heading to bed.
I woke up to a light sprinkle falling on my tent, but it quickly subsided and I was able to set off onto a mostly dry trail. I only had eleven miles to go to get to Bennington for the night, and I started pushing to try to get the miles done quickly. There was only one noticeable climb right as I started the morning, and after that I swung up and down on a few small hills that led through pine forests and past multiple marshy ponds. These ponds were especially fun to look at because right next to where the trail crossed the wet marsh on small boardwalks I could clearly see beaver dams holding back all the water, and there were large dome shaped lodges way out in the middle of the ponds.
The dams were so watertight that there were grasses and small trees growing up out of their dry sides, and the transition from pond on one side of the dam to bog on the other side was a cool change to look at. The final decent to the road was bone jarring as I carefully lowered myself down another large uneven rock pile. Thankfully I had two feet stable on a rock when a huge blast came from somewhere to the right, and echoed back and forth between the mountainsides, what a startling sound to hear in the middle of the woods! Once I got to the road I spotted a construction sign that warned about blasting up ahead, a bit of a late warning for me. I collapsed by the road to wait for my ride to town, which came after just a couple minutes. Once in town I shoved a burrito in my pie-hole and resupplied before charging into my motel room and heading straight for the shower.
That fancy lemongrass bug spray I was gifted smells good at first, but not so much after five days worth of it are slowly melding with your own BO and turning into a slightly lemony stink bomb wafting off of you whenever you move… anyway I desperately needed the shower and the laundry that the motel offered. After transforming into the semblance of a normal clean person, I dropped into bed for the rest of the afternoon and night.
I grabbed breakfast from a great diner in town (home made strawberry rhubarb jelly!), before getting out of the motel room and then wandering back into town to find a spot near an outlet to sit near. I was going to have another few hours in town to wait around because I was expecting another visitor: boyfriend Ben was coming back out for a whole week! After a few hours of waiting I got a ride back to the trailhead and met up with him, and then we crossed the parking lot and started uphill. The ascent out of the gulch was long but not as steep as the descent had been, and we made good time hiking up the hill. Another major plus was the cool weather and strong breeze, which felt great during the climb. After the initial hill we went up and down a series of hills, but trended upward toward the top of Glastonbury Mountain. The last mile, as usual, was the toughest one of the day, and we finally crested the hill and caught a glimpse of the Glastonbury shelter. The wind was much stronger up near the summit of the mountain where the shelter was, and we quickly got a little cold as we cooked dinner. We tightened the guy-lines and stakes on our tents so they would withstand the windy conditions, and then hopped into our sleeping bags for the night.