Day 101: Trail Angels.

July 10, 2017

9:04 PM

Total Miles: 1483

Day 100

Last night Bill took us all to one of his favorite pizza joints after he did some trail maintenance.

I was fortunate he picked up another hiker named sunshine on the way back so that on the way to pizza he had to take his motorcycle.

Again he smiled at me and he asked if I wanted to ride with him.

Oh you know it!!

We got to the restaurant.

He warned us though to probably only order one of their giant slices.

We laughed. How big could it be. Alex and I both thought we could definitely do two.


The pizza came out.

And Bill was absolutely right.

They were ginormous. 😂

I thought maybe I should of went with the spinach roll like Planner did.

She was fond of it for sure. I mean just look at that face. 😂

We headed home after we stuffed our bellies and hung out in Bills basement. 

Ahhh. I felt relaxed and had accomplished all my “chores” like laundry, showering, and blog stuff and felt content.

Bill turns out to be a doer. He asked us before we went to bed if we want to go to a hot air balloon lift off.

Say what?

Yeah… So we woke up early at 5 and headed to a hot air balloon festival and made it in time to watch them all air up and lift off.

This. Is. Awesome.

Absolutely fantastic and unique way to start our day.

I was in awe. Why do they look so cool and why can I not stop taking pictures.

We all were in awe. Thanks Bill… You are one of the best trail angels out there. I don’t know If I have met someone who cares about hikers as much as you!

From there he took us to the trail head to start our hike and I unfortunately had left my trekking poles at his house.


Bill was kind enough to make the trek back home and back to where we were just to bring them to me.

Tia and I started out 2 hours later than Planner and Alex. Ut oh.

But there was nothing I could do about it. So there is no point in worrying.

I quickly was happy that we had actually been pushed back because a little after we started hiking a gentleman came up behind us called New York Steve.

New York Steve was an incredible guy. He hiked behind Tia and I for two hours and we chatted about everything under the sun. 

He was a trail angel That has helped out many many hikers. 

We came to find out that he was an ultra marathoner. I instantly was excited to learn more.

So I heard about some of the races he did and which ones were best and heard his stories.

I was thrilled to have met his guy. Such good, positive, genuine vibes from him.

Tia started slowly but surely learning the Ropes of the trail.

Tia brought with her some real food that she vacuumed sealed. 

Thankfully she likes to share.

So I had a delicious egg and cheese sandwich on a bagel… On the trail.

It was one of the best lunches yet.

We crossed into Connecticut today!!

I was so happy Tia was able to experience crossing into a new state with me.

It was nuts… I have 4 states left?!

This is nuts

We ended the day with a 18 mile day, we had planned for more but having such a late start.. It just was not going to work.

No worries.

We ended up at an awesome shelter with great water and tent spots. I wasn’t complaining.

Day 101

The crew and I woke up early around 5 we had tentatively planned for a 25 mile day to get into falls village, CT for Tias friend to pick us up.

It was a perfect cool morning.

We hit a flat stretch of terrain and I about fell asleep.

I slept amazingly… However, the easy terrain made me want to fall asleep… I was yawning at every turn.

After some more up and downs I started to wake up. Even more so after lunch and another egg sandwich. 😁

Planner caught up to us at lunch and hiked with us.

We reached 16 miles. A spot we had tentatively told Tias friend Roger that we might be at.

We arrived there around 230 and were ready to be picked up.

Planner decided to stick with the plan and moved on to meet Alex.

Roger got us and took us back to his cottage in Pine Grove.

And oh my….

We were SO happy with our decision.

Pine Grove was like another world.

Such neat looking houses with vibrant colors.

Roger gave us the tour and man…Such history here! Some buildings since the 1800s.

Roger was so welcoming and treated us with such kindness.

We even got our own beds.

I was definitely excited about this.

My. Own. Bed. 

I plopped myself down and was stuck there. I just didn’t want to move. At all. My own paradise.
Tia was feeling the same way.

Finally, we decided we should shower. So we did, had some beers after on Rogers porch.

We then decided to go on an adventure to Great Barrington and eat dinner for some yummy pizza.

On our way we took a little detour by a couples house that had ponies!

They were therapy ponies and they saw us slowly drive by and welcomed us back.

I immediately fell in love and thought of the Grayson highlands. Man… This journey has been incredible..

We went to a place called Baba .Louies. They had a pizza named after me…

Obviously, I had to get it.

And it was one of the most unique best tasting pizza I have ever tasted.

We headed back home and I felt so extreme blessed.

Roger, the thank you for being yet another amazing, welcoming trail angel!

I am sad Tia is already leaving. The last 3 days have completely flown by. But I am so so so happy it all worked out unbelievably smooth.

Her little comments about trail life, ones that I had at the beginning always made me smile and take me back.

Little comments about the wind, the water, the wildflowers.

It was nice. And such a blast to have someone I knew out here.

Tomorrow saying bye will not be the easiest thing to do.

Tia. Thank you for being a hell of a friend.

Ozzy and I will cherish and miss you.

Iz and Oz

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