Days 148-155 Marshachussetts: Land O’ Lakes and Ponds

If you thought we loved Connecticut, wait till you hear about magical Massachusetts !

Our welcome into the state was less than ideal with the steep rock scramble down Bear Mountain. Luckily it wasn’t too long of a scramble. We quickly made it down into Sage’s Ravine, an area we were excited for after our friend Harrison told us how beautiful it was. Our plan was to camp at the campsite that night.

After getting water, we crossed the creek and hiked into the site. It’s a big site! Our mistake was not taking a photo of the map! We found our way to the “group campsite” where several thru hikers were already set up. One was our buddy Papaw! We hadn’t seen him since PA! Foodie, On My Knees, and Sushi Bat rounded out the group. They told us it was going to rain around 9, so we set up accordingly.

Sure enough, right about 8:45 it started to drizzle. We hopped in the tent to finish our dinners then I went out in the rain to search for the bear box. I had seen the sign for it, but it was dark and I walked in the wrong direction for longer than I should have…

The rain brought cool air with it and we had a surprisingly comfortable night in the tent. In the morning, it was damp and misty but very comfortable. We packed up and struck out for a day that would include 2 more big climbs but also a trip into town!

The morning was just spectacular. We walked along the bottom of Sage’s Ravine for about a mile. The trail was rocky and rooty (slippery) as it followed the creek. We could see several good swimming holes, if it wasn’t 8am and mildly chilly we would have loved a dip.

The forest is an old growth Hemlock forest. The rain made it all cool and damp, the way that forest likes to be. It was beautiful with the sun slanting through the trees. One of our slower miles because we kept stopping to admire it.

Sadly, we made it to the end of the ravine and began the climb up Mt Race. It was another one that looked scarier on the map but was way better in person. What the map doesn’t tell you is that you spend a long time on the side of the mountain on big exposed rock slabs!!

The sun had come out so the rocks weren’t slippery.. and it was heating up again. But we had a breeze! And the VIEW! It was the best panorama and for the longest time we’d had in a while!

We just loved it. The summit of Race was mildly underwhelming, given the drama of the way up. But we were still happy to be there.

We went down a bit then started climbing Mount Everett, also above 2,000 feet. This one had a steep, rock scrambly ascent. We saw our first wooden steps re-barred into the rock face.

With relief we made it to the top. We were proud of ourselves for not only making the climb but for doing it before the predicted thunderstorm rolled in!

The summit didn’t have a good view but a stone picnic shelter a short ways down did. We sat down to admire it and catch our breath for a few.

We made it down to the shelter, where Pinky made a very long walk to the water and we took a good long lunch break. As we were eating scary clouds started rolling in and Knees told us his weather app said it would rain soon. We thought we were done with the trickiest part of the descent but we still didn’t want to get caught in the rain for too long. We hurried to pack up and start getting down the mountain.

Turns out the worst was yet to come. We had 2 more hours of steep steep rocky descent! One part was literally an exposed cliff!

Great view tho

Slowly but surely we made our way down. At the road crossing that marked the actual end of the worst of it we found a generous water cache! We were happy to be able to fill up without having to make a trek to an unreliable spring…

Next we had several miles of walking through almost flat marshes,

pine forests,

and fields.

Several fields

There’s a spot somewhere in this section where a handful of locals do regular trail magic but we were too late for it. We heard about how great it was from other hikers the next day, though!

It was pretty hot down in the valley. When we finally made it to the road into Great Barrington I was sweaty and tired and so ready to be there. The small bit of wandering we had to do to find the road after we missed a turn and wound up in someone’s back yard did not help my mood…

It was like 4 miles to our hotel so we planned to hitch. Within 2 minutes of sticking his thumb out Pinky got us a ride! The nicest woman pulled over for us. I got to ride in the back seat next to her delightful 4 year old son! He pulled out his Spider-Man backpack so he could show me all his stuff. It was very fun.

She dropped us at the hotel where we spotted Knees, Sushi, and Foodie outside. They told us the hotel had overbooked and was sending them across the street! I went into the office and, sure enough, they told us the same thing. So across the street we went to a much nicer looking hotel…

Where they tried to charge us like $30 more than the price I had been quoted at the other one! I put my foot down and got them to drop it down to the original price. It wound up being quite the steal, in my opinion. It was still not the hiker rates we have been used to, usually the hiker rate is in the $50-$75 range, this was $120 but the hotel was absolutely twice as nice as the cheap places!!

We had a massive comfy California king bed, just a giant room, and breakfast in the morning was the best hotel breakfast ever. They had incredible cinnamon buns, omelettes (!), and a pancake machine! Just incredible. Pinky ate an insane amount of carbs. And we could walk to several restaurants and the grocery store. The one major bummer was that the brewery was closed because it was a Tuesday.

We had a slow morning the next day. We did our laundry, reorganized our food, and Pinky patched his sleeping pad again. By the time we were ready to leave, the brewery was open! So, of course, we had to go for lunch.

The food and beer was incredible. Even more incredible was the WEATHER! It had cooled off significantly and there was no humidity whatsoever! It was actually a pleasure to be outside. Energized by this change, and the food and beer, we set out for our last chore before hitting the trail- a visit to the post office!

We were like 2 miles from the post office, so we planned to hitch. Once again, just after sticking our thumbs out we got picked up! This time by a very nice older man in a truck who let us ride in the back. I love riding in the back of a truck. He dropped us at the post office, we grabbed our several packages, then went across the street to this cute shady seating area in front of the cute library to open them.

I had new shoes; a care package from my 2018 trail sister Venus

and one of my best friends, Hannah, mailed us home made cookies (along with my prescription med she’d picked up for me.) It was quite the haul!!

While we were going through everything a very nice man walked up, asked if we were hiking (a rhetorical question with all the mail and backpacks strewn about) then asked where we were going back to the trail and if we needed a ride. Our drop off point was in the wrong direction for him, so he apologized and left.

A little while later, after we’d reorganized, bumped some things ahead, and were ready to leave, the nice man came back and said he’d take us anyways! We were thrilled when we got to his car and it was a TESLA! Neither of us has ever ridden in one! Needless to say it was our favorite hitch yet! He was super nice and told us about being a ridge runner in the Connecticut section 30 years ago!

Of course, we got a late start on trail, it was 2 or 3 in the afternoon. But we were only doing about 6 miles to the first shelter. It was a little warm but not too bad, all things considered. We had a bit of a climb, but it was quite fun. Plus, the fresh kicks felt GREAT! My feet were absolutely loving all the cushion.

Part way up we ran into our buddy, Two Step! We hadn’t seen him since PA! We caught up for a few minutes then continued on up the rest of the climb.

The climb ended at a rocky out cropping with a view across the valley to Mts Race and Everett.

We sat for a good while. For the first time in a long time it actually felt good to sit in the sun. What a change!!

After some technical hiking along the ridge we made it to the shelter. Papaw was there, along with Two Step (set up in the best spot with an open view of the valley and the moon rise! We were only a little jealous), and Caboose and Caleb, a dad and son section hiker pair. We had fun eating dinner with them, but the best part was that it was cool enough for me to break out my fleece!!

We slept without the rain fly for optimal full moon viewing. It was the coolest night in a long time and we loved it!! Getting out of the sleeping bags in the morning was a sad event.

Massachusetts is extremely against stealth camping, as was Connecticut, but MA really took it to a new level. So we had to commit to a 22 mile day or a 12 mile day so we could stay in an approved location. We chose 22 since that would put us at Upper Goose Pond, an enclosed cabin with a caretaker that we read was not to be missed!

Pinky managed to fit in a quick chess game with Caleb over breakfast and we still made it out of camp at a reasonable hour. We kept up a good pace all day and tried to be mindful of our breaks.

Hiking in MA is just lovely. We passed about 5 ponds that day. Some actual ponds, some beaver ponds.

Actual pond

Beaver pond

We walked through some fields, some bogs and some beautiful good smelling forest.


In the afternoon we stopped at the Trail Stand, a tiny barn with an old fridge full of sodas and icy pops plus a small variety of snacks!

Next to it was a picnic table full of SOBOs and a big jug of water. We snacked and talked with the SOBOs. They told us about the Cookie Lady, a trail angel who makes cookies for hikers! She also has an extensive pick your own blueberry patch, they each had a bag of blueberries!

We still had a ways to go to Upper Goose Pond. The first mile or so was through another marsh. Before we started our next climb we passed a big water cache. It was pretty helpful, there was no water until the pond.

We burned out the last miles to Upper Goose Pond. They were mostly chill miles but we were still very ready to be done when we finally made it, 22 miles is a long day.

When we arrived at the shelter we saw tons of hikers. One told us the caretaker could be found down at the beach and we needed to check in with them before getting set up. We went down to the pond and met 12 year old Fern and her mother, the weeks care takers. Fern was clearly living her best life. She told us everything we needed to know about staying there, most importantly that pancakes would be served starting at 7am!

We set up our tent with a view of the pond and went to eat. It was getting dark and we were hungry. Most other hikers were heading to bed but about 6 of us were left eating at the covered picnic table behind the cabin.

Suddenly, the air shifted. I looked at the sky and thought I saw rain clouds. But I didn’t think rain was in the forecast!! Someone said they felt rain drops. We hadn’t put the rain fly on our tent!

I left my stove in Pinky’s care and ran down the hill, saying lots of bad words and hoping the rain wouldn’t get heavier. I struggled to put the rain fly on in the dark. It was difficult to discern the color coded corners of the tent and rain fly in the red light of my head lamp, and I couldn’t get it to switch to white! Finally, I got it on and threw our packs in. Then I ran back up the hill to finish dinner.

It rained all through dinner, but we stayed dry since the table had a roof. It was pretty fun, actually. When we went to bed it was with some disappointment because we’d been excited about watching the moon over the pond. Alas, it was still nice listening to the rain and being cozy in the tent.

We got up early the next day so we could get pancakes. It was cool and misty. The pond looked just magical.

The pancakes were incredible, but the most impressive thing was that Fern and her mom churned out enough pancakes for almost 40 hikers! PLUS fresh coffee.

After breakfast we packed up then lingered on the pier. A group of SOBOs came down to do the canoe challenge- see how fast you can canoe around the island in the middle of the pond. One couple were rowers in college and they did it in 7 minutes!

After the fast people took a turn, we took a leisurely row in the canoe. It was magical.

Eventually, we tore ourselves away from Upper Goose Pond. Just before we left I noticed this GIANT MUSHROOM!

It was about the size of a trash can lid. Biggest mushroom I’ve ever seen. 

Leaving the pond was sad, but we had the Cookie Lady ahead!! The next section of trail was chill but I felt horrible. I was tired and cranky. Our Plan A for the day was to hike past the Cookie Lady, but the closer we got the more I knew I wanted to do Plan B- stay with the Cookie Lady.

We arrived mid afternoon and were immediately offered hibiscus lemonade and chocolate chip cookies. We each chose one of the numerous comfy chairs and Relaxed. After 45 mins or an hour we decided we were officially staying put. The vibe was too strong.

The Cookie Lady is actually The Cookie Lady 2.0. She took over from the previous Cookie Lady who had been a trail angel for several decades. A Massachusetts newspaper did an article on her as part of a series. One of their journalists hiked the MA portion of the trail this month. She was hiking it around the same time as us but, sadly, we never met her. (Was going to link to the article series but there’s a paywall… it’s the Berkshire Eagle paper, if you’re interested.) 

It was a sunny afternoon, not too hot, not too cold. The breeze was blowing. There were 3 sweet dogs lazing about. How could we leave?

I wandered through the blueberry field, eating and picking for about 30 mins. I ate until I couldn’t eat any more blueberries. It was glorious. I laid in the hammock for a while. Pinky tried out all the chairs and tried to discover which one made him the best at chess.

For most of the evening it was just us. The other hikers we’d come in with moved on and it seemed like nobody else was coming.  Around 5 or so The Cookie Lady came over and said she was going out to get pizza and offered to pick one up for us. Of course we said yes and ordered 2. Later a few more hikers did roll up and we felt a little bad about the pizza situation… 

As evening fell the air got cooler, until it was actually cold! I had all my warm things on and still had to get in my sleeping bag to be comfortable. When it was just about dark the Cookie Lady returned with our pizzas. We wolfed them down then snuggled up in bed.

We slept sans rain fly so we had a good star and moon gazing night. The moon was only one night past full so it was Very bright. We slept in a bit in the morning and were slow to leave. I had to pick some more blueberries since I ate up what I had with breakfast!

With much sadness we said goodbye to the good dogs and the good vibe. It didn’t take long for us to perk up, though, the small town of Dalton was just a few miles away! Lunch would be at a deli!

The lazy day before had me feeling much refreshed. We burned out the 8 or so miles to Dalton. The town was super cute !

We stopped at Tom Livardi’s for water. He’s a trail angel who leaves water out for hikers and lets hikers camp in his yard. He does not let hikers use his bathroom. Instead there’s a pee corner in the yard and a walk to a gas station for number 2…. Still appreciate the man and 100% understand keeping hiker trash in the yard.

Lunch at the deli was awesome. Pinky got some giant meat sandwich and I got an eggplant parm sub. We also got fries and Vanilla Coke. Perfection.

We needed a slight resupply but the Wal Mart was several miles away and we didn’t want to spend a bunch of time hitching. We were feeling inspired and energized, we thought we could make it to the next town. So we did a gas station resupply, not the best but not the worst.

The trail continued through the rest of the town. It was so cute, we had a lot of cute house envy. This tiny historical house at the edge of town was the winner.

Then it was back into the woods. We climbed up a ridge and made it to our Plan A campsite around 4:30. We had a nice long chat with a local man, he told us all kinds of detail about the trail ahead, it was great. Since it was still early, we decided to do the remaining 4 miles into Cheshire.

They were a Chill 4 miles. In the last mile or so we heard a band start up down below! This got us moving a bit faster, we were curious! The trail dumped us out into another neighborhood. Before long, a family passed us. They asked if we were just getting into town and congratulated us on our timing. The town fire departments annual car show was happening down at the elementary school. There were cars, live bands, food, and fireworks after dark! We were thrilled!

We hustled down the road and found our way to the Father Tom campsite. A public/private campsite close to the middle of town where hikers can camp for free. We got set up, then Ivy League, former thru hiker, fed us some trail magic hamburgers!

After burgers, we walked over to the car show with Johnny Walker. The car show was so fun!! We wandered through and checked them out. Pinky’s favorite was a Jaguar XKE Just like one he and his dad restored when he was a kid.

After cars we got food! The fire department tent had kielbasa dogs and corn on the cob. Yum! We wanted ice cream but we were out of cash and it was cash only. Sad. By the time were done eating it was getting chilly, so we headed back to the campsite.

The fireworks were supposed to start at 9 but 9 came and went… maybe they were cancelled? We heard the band end, then vaguely heard some people talking.. then around 9:30- boom!! The fireworks began! We had an almost perfect view from our tent. There’s nothing better than being snuggled up in your sleeping bag while watching a fireworks show! It was an incredible show. A woman we talked with at the show said it’s her favorite display of the year, we could see why!!

After the fireworks we went right to sleep. What a way to end what had already been such a fun day!! And to think, we almost didn’t go to Cheshire!

In the morning our sleeping bags were wet. There had been a pretty heavy dew. Woops. We thought this might be a sign that our flyless nights were coming to an end. That’s the trade off for the cool nights.

Today was the day we would climb Mt Greylock, tallest peak in Massachusetts and our longest climb in hundreds of miles. We were excited!! To add to the excitement of the morning, Ivy League was serving up fresh coffee from a tiny coffee pot !

We walked through town and back into the woods. In a meadow we caught a view of the peak of Greylock, notable for the big stone tower on top.

Hard to see, but it’s poking out beyond the ridge in the foreground

Then we started climbing. And kept climbing for about 2 hours. It looked pretty scary on the elevation map.

But the actual experience was pretty fun! The climb never got very steep. Mostly, we were just thrilled to be in another Christmas tree smelling forest! Every five minutes we were saying “It smells SO GOOD!” I kept taking deep breaths and dreading the moment I’d become nose blind to it (I never did, I stayed focused.) It was our favorite mountain yet, for sure.

We knew we were close to the summit when we crossed the iconic tiny pond and tiny cabin.

About 10-15 mins later we came out at the summit! It’s an incredible summit! We were there on a Sunday so it felt slightly like mountain Disney world, but it didn’t bother us. We found a spot in the grass by the overlook and spread out for lunch (literally, our sleeping bags were wet and we had to dry them out!)

The sleeping bags were like a thru hiker flag. Several people asked us if we were thru hiking. Two of them were former thru hikers! One hiked just a few years ago, the other hiked in like 1998! They both said we had the best ahead of us in VT, NH and Maine!

After a long lunch we walked over to the lodge to fill up water. We noticed some bikers drinking beers. We didn’t know there was beer there! We decided we could stay for one beer. We split a bomber of this incredible English IPA from a local brewery. What a treat!

Properly fueled, we began the descent.  Boy howdy was it harder than the ascent!

In the first few minutes we passed an adorable family- first we passed dad and a dog. Then mom and 4 kids. Then another dad with a 4 or 5 year old girl wearing a Pegasus shirt, dad was so proud of her for hiking the whole thing herself! We cheered them on! Then we passed grandma and grandpa who asked if we had seen 5 kids, 3 parents and a dog, and if they were close to the top. We said we had and cheered them on, too!

We took a break at an overlook of the valley. Spoons, Johnny Walker, and David caught up with us. We chatted, snacked and headed on. The descent went on and on and on. But finally we made it to the end. We found ourselves in a neighborhood in the town of North Adams. At the elementary school there was a hiker bulletin board with coolers below it. We shouldn’t have stopped. But it’s impossible to resist a cold soda!

We sat down to drink our sodas. Mistake #2. Then we ate some chips. And made lots of complainy sounds about hiking 2 more miles uphill to a campsite. We watched a grey squirrel and a red squirrel get into a screaming match. About 20 mins later, Spoons, Johnny Walker and David rolled up. They sat down, too. We all made more complainy sounds.

Then Spoons said the magic words- “There’s a trail angel around the corner who will let us camp in her yard.” Game over. Spoons sent a text and a few minutes later we were all walking over to Renee’s house.

Renee not only let us camp in her yard but she gave David a ride to his hotel a few miles away. She let us use her bathroom (!) and in the morning she made us coffee and shared toast and fruit with us!! She was SO sweet and we had so much fun talking with her in the morning. The trail magic (hiker trap) by the school is maintained by her and a few friends. We were so glad we stayed there!

Our choice to stay in town meant we had 18 miles instead of 16 to do the next day, but we regretted nothing that morning. Hiking up the hill was way easier first thing in the morning with a belly full of toast and good coffee. We had one last view of Massachusetts from some rocks at the top then it was smooth sailing through the forest to Vermont!!

Leaving Massachusetts was so sad. We met so many trail angels, saw so many beautiful ponds and forests, climbed some very fun mountains, and loved every single small town. For such a short state (only like 90 miles!) it was jam packed with surprises!

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Comments 2

  • Kurt Oswalt : Aug 28th

    I’ve really enjoyed following you and reading your blog. Wishing you both the very best success and safety! God bless.

  • Smitty : Sep 2nd

    Western Massachusetts is nice isn’t it l. Civilized but rural. Great story


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