Week 3: Dalton, MA to Bennington, VT (Mile 1568.7 – 1632.2)


Mt. Greylock

This was the first big* mountain I’ve climbed since Katahdin last August. It wasn’t as hard as I anticipated it would be, which was a nice surprise. When I reached the top there was a wedding going on, so there would be no celebratory beer for me at the Bascom Lodge. I tried to finagle my way in to the wedding by asking two attendees at the viewing area if either of them needed a date, but neither of them were convinced Roan would be a good date. Obviously, they are fools because she can Cupid Shuffle like no other!

* my definition: elevation of over 2000′

This is what the Washington Monument has looked like the past few years, so it actually reminded me of DC :)

This is what the Washington Monument has looked like the past few years, so the Greylock Monument actually reminded me of DC 🙂

The view of North Adams from Mt. Greylock

The view of North Adams from Mt. Greylock

I stumbled upon my first trail magic at the summit- apples and bananas! Yaay fruit! Now it really felt like I was living out Hudson’s Adventure Island.

At the Wilbur Clearing Shelter I saw Tangerine and met a ridge runner named Sawdog. Sawdog spent most of his career jumping out of helicopters and fighting forest fires. In telling us about his adventures he suggested I look into ridge running in Denali to fund my future Alaska adventure. Great idea!

Follow the Inner Tube Teens

The next day I persuaded Tangerine to join me in venturing into Williamstown, MA via Route 2. I said “Wanna getta beer?” and he said “Oooooooh. Yes.” It was a tough sell.

We stopped into Nature’s Closet where I had bounced my ATC guide forward. Surprise bonus! Nature’s Closet is dog friendly and Roan got to play with the owner’s dog Willy while Tangerine and I had delicious smoothies. Roan gets plenty of exercise on the trail, but there’s no substitute for play time with other dogs.

While lunching at the Purple Pub Tangerine noticed that according to Google Maps the Hoosic River was super close by. We were melting under the heat of the giant nuclear furnace fondly referred to as the sun, so after checking with our waiter that swimming in the Hoosic wouldn’t be a completely disgusting mistake, we followed Google maps in the direction of relief. We turned off the road by a power station and followed a gravel path for a few uncertain minutes. We were really starting to question whether we were going to find water or just wander deliriously in the heat when suddenly a few teen boys with inner tubes came from out of the woods onto the path in front of us. We followed them to the Google promised land- a small beach where a few families and dogs were playing, swimming and lounging. Surprise bonus #2! Roan got more dog playtime!

The water was cold but exactly the right temperature to stop my insides from boiling and diffuse the mental heat haze. After a few hours of swimming, sitting, and thwarting a small chihuahua from humping Roan we decided to make our way back to the trail. We took a detour by the packie and grabbed some tall boys of ginger-cider.  We hitched a ride from some lovely gentlemen who insisted we stop at their house on the way to fill up on water.  It was so hot that I couldn’t make the 1.7 miles to the Sherman Brook Campsite without a dip in the swimming holes along the way.

A Kiwi, Comedy & Another State Line

We had some lovely neighbors at the campsite that night. Two sisters named Three Socks and Marilyn (no trail name yet) were doing a section hike together. Marilyn is a costume designer and created all of the costumes for Spuds McKenzie!


This could be you, Roan! We’ve got connections now!

We also met a kiwi hiker name Puku (Maori for tummy) who had just finished the 273 mile Long Trail – in 11 days! He was about to go back to Canada to finish his immunology PhD. He was a fun, easy-going dude. With such great neighbors and the Vermont border crossing coming up I convinced them to let me tell some jokes and cross Massachusetts off my list. This time I didn’t phone it in. Tangerine built a fire, my audience of four sat close together on the tent pad, shared some ciders and had a great time! I did a proper 8 minute set and it felt really good. Massachusetts is checked off the list!

3 socks

Three Socks and Marilyn


Me, Tangerine and Puku

Me, Tangerine and Puku


The Long Trail and the AT overlap for 105 miles

The Long Trail and the AT overlap for 105 miles

Beaver bogs are nature’s infinity pool. And raisins are nature’s candy.

Hitching Tips for Super Cool Hikers Only

By the time I reached mile 1610.6 I had been on the trail for 201.6 miles (18 days). I had slept indoors once, and had taken one shower. So when Tangerine planted the idea of staying in Bennington in my head, it didn’t take long to feel I had earned an overnight town stay. The deciding factor on choosing the Knotty Pine Motel was the pool. It had been a scorching hot few days.

We caught a hitch using my patented hitch-getting method: the Haunted Mansion Bop. I remember the 3 dapper ghosts doing a sort of up-and-down squat motion as they gestured their thumbs, but giphy tells another tale. Regardless, I do it with a bopping-knee squat motion. Even if I don’t get a ride right away, the rejection rolls off easier when I look goofy and ridiculous. And I guarantee it’s more eye-catching than simply sticking out my thumb (BOR-ING! That lame-o hiker doesn’t have any fun small talk to make! Pick up the Haunted Mansion hiker with a non-haunted dog instead!).

They're kind of squatting

They’re kind of squatting

Tangy had a hankerin’ for some good breakfast and our hitch couldn’t recommend a place. Once again, Google answered the call:  The Blue Benn. For some unknown reason I love love LOVE sitting at the counter of a diner. I have no idea why it makes me as happy as it does, but it does. It was super hot and there wasn’t any good shade for the Roanster, so we had a cup of coffee at ye olde counter, and took our order to go. We sat in the shade of a tree in the park across the street and D’Tangelo enjoyed some killer blueberry pancakes while I had cornbread french toast. OMG so good.

I hit the library after that to work on last week’s post. Bennington Library is not dog-friendly because a cat named Pete lives in the Library. Score one for cats.

Go Visit Your Friends on the Trail

My friend Mike drove in from nearby NH (Not really; it’s 80 min by car. Thanks, Holmes!) and we drove around Bennington being silly until it was time to eat ice cream. Then Mike played shuttle-driver/trail-angel for me and Tangerine so we could re-supply, which involved extensive Googling to find denatured alcohol (Home Depot was the only place that had Heet). It was just a few short hours, but spending time with a non-trail friend was really great. Please do this for your hiker friends if you can. They will always remember it.

Me, Benny & Holmes

Me, Benny & Holmes

Because you can't sit on Benny

Because you can’t sit on Benny

After Holmes headed back home Tangelia Jolie and I grabbed a 6-er of some local Vermont brew from the packie, ordered a pizza to the pool and chilled out there.

The next morning the weather was much cooler, so we hit up the Blue Benn again.

diner happy

Two Happy Hikers

It's a grilled sugar donut with ice cream

It’s a grilled sugar donut with ice cream

This is dog friendly- offering to give Roan some ham :)

Dog friendly is offering to give Roan some ham 🙂

This is dog-tolerant masquerading as dog-friendly

Dog-tolerant is restricting her to lay on the floor only

The Blue Benn was the perfect end to a great town stop and my 2nd week on the trail. Tangerine still regrets not packing out some of their homemade pie. I agree, that was dumb.

What’s Next!?

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Check back in next week to find out about the band of Long Trail hikers that Tangerine and I got mixed up with, the most unique comedy show I’ve ever done in my life, my time at the famous Yellow Deli, and a stupid amount of pictures of me with many, much moosen!!!

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