Days 103-111 on The Appalachian Trail—Connecticut and Massachusetts

Random Thoughts

The further North I go it seems the opportunity to meet other hikers on the trail seems to be diminished. In the last part of New York there was a small cluster of thru hikers and flip floppers, now it is rare to see anyone. Having started in the winter, the isolation of the green tunnel of spring is intense. It is necessary to wander off trail to see more notable things and get a flavor for the region. Some interstate rivalries exist up here. My friend Heidi, a native of New Hampshire, commented on my picture at the Connecticut State Line that it is the “Gateway” and not part of New England. The war continues.

Cultural Differences 

I take issue with being charged $4.08 for a fourteen ounce glass of unsweetened tea and no free refills. Perhaps word of the joys of sweet tea and unlimited refills hasn’t reached this far North after all of these years. Then again “The Boston Sweet Tea Party” isn’t in recorded history as never could anyone so foolishly waste the “Wine of the South”. I’ve tried to avoid the subject of biscuits and gravy as to not give away the fact that I hail from elsewhere. A translation dictionary for many phrases would be helpful. Who could know that “PSDS” means pierced ears? 

Company on The Trail: Battle Buddy

Back In Pearisburg, Virginia and again in Harpers Ferry, WV I had the good fortune of meeting a hiker who started two days before me in early January. At our second meeting Angelika, The Hiking Tomato, and I hatched a plan to hike together. By together I mean the same geographic miles on the same day and camp or lodge in each other’s immediate vicinity. She has a quicker pace and neither of us requires constant chatter while hiking. This has prove beneficial in a multitude of ways. There is someone to share a few words with, a constant in the day, encouragement, a break in the isolation after 4 1/2 months. Making good mileage every day, and some feelings of depression have subsided.


Days 103-105


Connecticut I Hardly Knew You

A little over two days and done. Nothing of note except for the ice tea issue, friendly people, great scenery, and some beautiful covered bridges. My Canadian friend Gazelle/Solar completed the 53 mile Connecticut Challenge in less than 24 hours. Quite the impressive feat! Crossing the state line with THT feels like a huge accomplishment. I felt a little stuck in New York after my calf issue. More progress, another state  closer to home.

After crossing the state line all the trail seemed familiar and rocky. A lot of slab walking, boulder hopping, climbing over peaks, and yes the occasional rattle snake. Roger’s Ramp was yet another rock squeeze and photo opportunity. This is the first time I took a lunch break on this thru hike at a little cafe near Kent, CT. That’s where I discovered the tea problem. I traveled off trail after the hiking every day in Connecticut and found wonders from waterfalls to beautiful covered bridges. You have to leave the tunnel to see the communities and culture. The beauty and history of the surrounding areas is worth taking time to see. My favorite memory will be giving Gazelle support and trail magic during her challenge attempt.  This was my first time in Connecticut and I would like to see more. There have been milestones and points of interest. Unlike previous posts there is not too much to say as it felt like “Welcome To” and “Now Leaving” were on the same side of the sign. Maybe I should have taken more time.

Days 106-111 Massachusetts 

One of the striking things traveling further North is the amount of history in so many places near the trail. The introduction into Massachusetts is a simple sign in the woods as you pass a stream. The only thing I had seen of the state previously was Boston. Again, a short time in a state and I need to make better notes of  the days. The effects of TBI become apparent as I recount each section. Then again there are many places listed as “ Cliffs” and “Ledges” on the trail.  Continual amazing views when the trail opens from the tunnel to show the expanse of this incredible part of the state. Seeing Mount Greylock in the distance and then experiencing the climb was a good day. The forest near the top reminded me of the forest near Clingman’s Dome. Fairy tale like and the mirror pond and cabin are the subject of many hiker’s pictures. The war memorial at the top is a fitting tribute to the sons and daughters who gave their last measure for our freedoms. 
Seeing wild turkeys by the roadside on the way back to trail was entertaining. Two steps into the woods and they disappeared. THT definitely hikes the cliffs with more confidence. The memory if Tennessee stays with me. I didn’t stay too long in Massachusetts either. While I don’t want the journey to end I am getting anxious to be home.

Final Thoughts 

The world is full of magic things, patiently waiting for our senses to grow sharper.
– W.B. Yeats

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Comments 7

  • Jenny : May 28th

    I’m always glad to read your posts and catch up on your amazing hike. Thank you for taking the time to write and keep your many fans in the loop. Enjoy each day!

    • Charles Gutierrez : May 28th

      It is a privilege to share this with you. I get a bit behind at times as I’m working hard out here. I try to enjoy some of the surrounding areas to get a flavor for what the regions are like. I’m happy you are enjoying the updates!
      Kindest regards,

  • Matt Chapple : May 29th

    $4.08 for tea!!! Bro – a Bojangles Southern Gravy Biscuit Combo and a biscuit and honey with a 32 oz. Sweet Tea with Fresh Lemon Slices and free refills… come back to The South Lands…We got you.

    • Charles Gutierrez : May 29th

      Send a care package. I haven’t seen a biscuit for weeks! Be seeing you soon.

  • Sherry Rouse : Jun 3rd

    It was fun seeing your pictures and reactions of going through Connecticut and Massachusetts. We finished up the 14 State Challenge last year and did a couple of sections around Bull’s Bridge in Kent. Then on to Massachusetts where we did a section near Bald Top in the October Mountains near my cousin’s house in Becket (where we were staying). I love sweet tea and biscuits and gravy too, so you’ll be done before you know it and can come south again! I’m assuming you eat southern in Montana?

  • Sherry Rouse : Jun 3rd

    I also forgot to say that we did a small section going up to Mount Greylock when we were here for a family reunion. My cousin’s husband did the landscaping around the Inn, so that was something we wanted to see. The tower/memorial was great too!

  • Janet : Jun 4th

    Glad to see you progressing and glad to hear your tales of a hiking buddy. I enjoy your photos and stories and continue to wish you good hiking.


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