Connecticut & Massachusetts on the Appalachian Trail

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Connecticut & Massachusetts Statistics:

# of miles:


# of days:


Average daily mileage:


Trail difficulty:




Towns Visited:

Great Barrington, Dalton, Cheshire, Williamstown

Days between Motel:


Average $ of motel:



Connecticut & Massachusetts Notes:





22.9 1460.6


27.8 1488.4


16.8 1505.2


11.7 1516.9


24.6 1541.5


23.6 1565.1


22.4 1587.5


Connecticut & Massachusetts Accommodations:




Sages Ravine Brook Campsite (Billy) / Silver Hill Campsite (Ben)


Camped near Gt Barrington Rd (Billy) / Brassie Brook Lean-to (Ben)


Monument Mountain Motel - Great Barrington


Mt Wilcox South Lean-to


October Mountain Shelter


Camped 2.5 miles north of Cheshire


Camped between Seth Warner and Congdon shelters in VT

Connecticut & Massachusetts on the Appalachian Trail

 Ben & Billy on East Mountain on the Appalachian Trail
Ben & Billy on East Mountain

Connecticut & Massachusetts

Goodbye to Will

Will and I roused ourselves for our final day together and headed out towards the Connecticut border. I wondered whether Billy had gotten out ok that morning – I think I slept as badly as he did worrying on his behalf. Soon into the state we began a series of ominous climbs – some of the toughest we’d had in a very long time. We were working hard and I was worried that this was a bad omen for Billy’s chances. I just kept reminding myself that Billy wasn’t bothered by hills like a regular human and would have breezed right by all this.

We made our way the thirteen miles to Kent where Will was to catch the bus home. The Connecticut difference was immediate right away. This place – like the other towns I visited in CT - was worlds apart from everywhere else we’d encountered on the trail. The place was heaving with well-heeled tourists and the facilities on offer were very different from what we’d gotten used to experiencing. The basics were covered, but we now had a range of boutique shops to browse too. I almost got carried away in the used record store, but figured that someone who resented carrying even a sleeping pad, probably would regret hiking with a 12” of Parliament’s Mothership Connection in his pack – even at such a great price. Will and I ate a final meal together, drank a final beer and said our goodbyes…

The pursuit

My focus was now on catching Billy. The plan was for him to get a motel room in Great Barrington and wait for me. The sooner I got there, the more time I’d have in town – that can be quite the motivation. There was one factor limiting my progress though – Billy had the tarp and there was rain in the air - I would have to limit myself to camping at shelters or take a gamble… Every time I came across other hikers I’d quiz them for news of Billy – had they seen him - and if so when and where?

I took the opportunity to stop for a soda at a small run-down garage near where the AT crossed a road. The place had seen better days and I entered the office hesitantly – flashbacks to The Texas Chainsaw Massacre running through my mind. I was about to shut the door behind me when I was stopped by the owner “leave that open boy, it's summer -wind'll close it when it's time”. The owner was an older guy who he seemed to fit into the ramshackle surroundings. I asked whether they sold drinks “Where you from Boy? Don't the garages have cold drinks where you're from? All garages have cold drinks.”. And where might I find these drinks? “You don't find them Boy, I go get them. What d’you want?” After a rummage in a back room he reappeared brandishing a can of cheap orange soda for which I duly handed over $1.20. We chatted a while –I found him to be entertaining in his own way and left feeling sorry the place was so obviously in decline.

Salisbury was to be the next stop and this easily trumped even Kent for obvious wealth. Even though it was a trailside town and they must get hikers wandering around all the time, I still felt quite out of place at the supermarket amongst the soccer mom’s loading their groceries in the back of their Mercedes SUVs. I had no time to waste though – I got what I needed done and pushed on to my very own shelter for the night.

Next day I was up and out at 5.55am - I had 17 miles between me and a cosy motel room and I wasn’t going to hang around knocking them off. However, at 5.56 I heard thunder; by 5.58 the sky had turned black; and by 5.59 a deluge was unleashed. I was drenched in seconds and, once the lightning started, not even the prospect of a waiting motel room was enough to make me brave the storm. I ran back to the shelter and sat frustrated until the weather cleared up a little. I then had the prospect of the notorious descent into Sages Ravine to contend with – turned slick and treacherous by the rain. The rain also had the unwelcome side-effect of bringing out an army of slugs to perch on every tree-root and rock that I could possible use as a hand-hold for the climb down. Thankfully I’m not squeamish – I reached the bottom, wiped the remnants of squashed slugs out from between my fingers and moved on into Massachusetts.

The trail was becoming harder and higher and the views more spectacular – the spectacular ascent of Race Mountain was enough to clinch it for me – I was glad to have left the Mid-Atlantic behind. For all its easy hiking, plentiful food stops and pleasant vistas, it was rather short on the ‘Wow’ factor. New England, like North Carolina, has plenty of that.

I made it to the road into Great Barrington and began my hitch. Finally I was picked up by a chap sporting a straw hat and driving an old Honda – the interior of which dotted with various crystals and icons. I’d immediately got the impression he was on the hippy side of normal – quite how far I hadn’t realised. We chatted as we drove and he told me that he had been down in Brazil for four months, visiting a ‘healer’ who he hoped would be able to cure him of the ill-effects of an injection of ‘meteoric iron’ he had previously taken. To my mind, this is like hiring a rhinoceros to repair the damage a bull has done to your china shop. Still, like so many of our distinctly odd benefactors he was a very nice guy whatever his beliefs and happy to drive me to the motel where I guessed Billy would be waiting. He wasn’t. It started to rain again. I wandered around the town trying all of the motels without success and started to get a little worried – perhaps Billy had a problem; perhaps he enjoyed hiking alone so much he’d ditched me altogether… Not to worry, I bumped into Strappy and the gang of girls we periodically met and they had a number for another motel, where Billy was indeed staying. They told me they’d seen Billy in Connecticut - they hadn’t realised what he was doing and sounded impressed when I told them…

The reunion with Billy was a happy one. He filled me in on his Connecticut Challenge attempt and we celebrated with too many burgers and too much ice cream…

Billy’s story: The Connecticut Challenge - in his own words

“I think I left around 4.45 or 5 that morning. I was still a few miles from the Connecticut border and made it there by sunrise. I even passed another campsite early that morning with campers fast asleep in their tents. Using your headlamp in the morning felt weird to me- as though I was a stalker of the night; however, I felt much more scared about what was around the corner this morning then I did when Ben and I hiked at night. I was unfamiliar with the terrain, and Ben was not going to be behind me. My adrenaline from being scared and my knowledge that I have little time to slow down if I want to finish kept me pumping out the miles. I ended up walking over 3.3mph over the entire time. Hiking Connecticut was a challenge, but there were two sections that were a breeze. My mind kept asking myself if this challenge was even possible to complete as I walked…I’m twenty miles in…usually my day is almost over…and I am not even halfway! The river bed walk (exercise trail) put some positive promises as it seemed to continue on for miles- with no one in site, except for the lady joggers every 15 minutes or so. There was also a “nature trail” walk that was flat as a pancake, but annoying because of its twisty turns to make the route longer for the average day hiker out to experience nature. I only stopped 15 minutes to throw down some peanut butter and crackers. I stopped at the gas station Ben referred to earlier, had a similar experience and bought an overpriced coke there and saw a couple Ben and I ran into sometimes. The Appalachian Trail runs around a pond here, which walking wise increases your trip length, but was not necessary. The pond was like walking an entire grocery store to get a gallon of milk, when you can see the milk is on aisle one right in front of you, but I’m a purist and want to walk every step, so I walked the marshy pond to end right where I had just come from. Halfway thru the challenge I also gained some adrenaline when I was storming along the hills and I all of a sudden looked up at the bottom of a hill to see Strappy and the crew getting water out of the creek. I needed water, but was too nervous to stop. Strappy and them, I think asked, “Where’s Ben?” I told them that he was behind me. So I basically blew off a conversation with Strappy and just breezed by them. Ben would later tell them that I hiked the entire state of Connecticut. They gave me props and Ben let me know that they were impressed, unfortunately even after finishing such an achievement, I was still too scared to talk to them. Soon after Strappy’s encounter, I was just starving for water. I took the next water source that was pretty crappy. Four young adults (2 male, 2 female) were just finishing up pumping water when I arrived. I took the crappy water and soon passed the group. I then came to the hydroelectric plant where families were swimming in the dams' water. I finished the 52 miles in 16hrs 45mins. I dropped dead at the Sages Ravine Brook campsite. I was too tired to eat, drank over a gallon of the nearby stream - within minutes, my muscles were locking up, I passed out.”

Back to the original line-up

Our town stop followed our now normal procedure – something like: food, laundry, food, store, food. Prices were distinctly higher than we had gotten used to further South and portions distinctly smaller. I had failed to finish my bottle of wine the night before and so, being the thrifty soul that I am, I had transferred the remnants to a Pepsi bottle and drank from it as we walked about the town – nothing like adding a little class to proceedings.

The going remained tough and the mosquitoes got tougher. We were still contending with poor water and yearned to reach Vermont and the promise of an abundance of beautiful clear water sources. We gave up trying to get decent water at one shelter and waited until we reached the home of ‘the Cookie Lady’ – yet another living trail institution. ‘The Cookie Lady’ and ‘the Cookie Man’ are a senior couple who live on a beautiful 20 acre plot near the trail. They make hikers welcome – providing water, a hiker box, use of the picnic bench and baskets of home-baked cookies. We met the Cookie Man and he duly fed us cookies, chatted to us about the trail and gave us licence to help ourselves to the 2 acres of blueberries growing on the land. He was a very likeable guy and we were greatly encouraged by our visit to the farm. It is the existence of places and people like this that make the Appalachian Trail, so much more than just a footpath.

This day we would be back to our Mid-Atlantic excesses – stopping off for burgers in Dalton and pizza in Cheshire. I got into a conversation with our waitress in Dalton about coffee cake – she was reluctant to believe that British coffee cake really does taste of coffee and I refused to believe that whatever she described as coffee cake could be something people would choose to eat. I got a free slice of cake out of the exchange and had to concede it was OK.

Summiting Mt Greylock took us up to 3,500ft – an altitude we hadn’t approached since the Shenandoahs. From our vantage point we could see bigger mountains in the distance - mostly in the direction of the trail. At the next road crossing, we stopped off for groceries and were walking back along the road in search of fast-food when a car pulled over and the driver offered us a ride. Once again this was a, doubtless, very nice and, certainly, very friendly individual, but I was scared. Obviously lonely, he seemed disappointed that we didn’t want to go far and he’d have to say goodbye to us so soon. He said how much he enjoyed talking to us and how he liked my accent. He volunteered that ‘voices’ were his ‘hobby’. I’m inclined to think of ‘voices’ as being an ‘affliction’ especially for men that live with their mothers and have a large collection of stuffed toy animals. As usual, I feel guilty for ridiculing somebody who had been so good as to help us out. Sometimes, I just can’t help it though...


Photos of the Connecticut & Massachusetts section of the Appalachian Trail:

Appalachian Trail
Appalachian Trail
Bear Mountain Observation Tower - Appalachian Trail
Bear Mountain
Ben on the Appalachian Trail
Benedict Pond - Appalachian Trail
Benedict Pond
Billy's view vista - Appalachian Trail
Billy's view vista
Bronze plague - Appalachian Trail
Connecticut Challenge - Appalachian Trail
onnecticut Challenge
Connecticut on the Appalachian Trail
Connecticut morning
Depot Street - Appalachian Trail
Depot Street
Giant's Thumb on the Appalachian Trail
Giant's Thumb
Henry David Thoreau - Appalachian Trail
Henry David Thoreau
Hoyt Road - Appalachian Trail
Hoyt Road
Interstate 90 bridge - Appalachian Trail
Interstate 90
Kent School cow on the Appalachian Trail
Kent School cow
Mount Easter vista on the Appalachian Trail
Mount Easter vista
Mount Easter vista on the Appalachian Trail
Mount Easter vista
Mount Greylock map - Appalachian Trail
Mount Greylock
Mount Greylock War Memorial Tower - Appalachian Trail
Mt. Greylock War Memorial
Phelps Avenue - Appalachian Trail
Phelps Avenue
river road - Appalachian Trail
river road
Shay's Rebellion Mounment - Appalachian Trail
Shay's Rebellion Monument
Appalachian Trail sky
Appalachian Trail woods

Continue on the Appalachian Trail:  Vermont