What the Connecticut Section of the New England Trail Taught Me About Finding Adventure in Your Backyard

Last fall I dedicated myself to doing a thru-hike in the spring of 2021. I had dreams of far-off places, new terrains, and truly wild areas. Like many, when I made those plans, I envisioned a world where COVID was contained and just a painful memory. Unfortunately, that world never came to fruition. However, I am lucky enough to be vaccinated through my work, and restrictions in my region (the northeastern USA) were slowly removed as our states became the model of how to fight and contain the virus.

My mind immediately jumped at the possibility of doing the Long Trail in my new home state of Vermont. However, between the LT being closed for mud season, my uneasiness to stay in potentially crowded shelters, and not wanting to miss out on some of the trail angels/ magic that the LT is known for during COVID-free years – it was clear that I needed to find a different trail.

The NET proved to be the perfect option – it is in my region, neither CT nor MA have restrictions on folx from Vermont traveling, and it doesn’t have an established trail community. While I am not thankful that COVID is still ravaging throughout the globe – it did force me to find the adventure in my local region on a trail I probably would have otherwise never hiked. New England is blessed to have incredible diverse, beautiful, and rugged landscapes nestled in between major population centers. Meaning that New Englanders have almost unparalleled access to recreation.

I would be lying if I said that I had heavily researched the Connecticut section of the NET. To be frank, I assumed it would be relatively flat with some occasional views. What I found blew those expectations out of the water (please don’t repeat this mistake – I promise researching the trail to prepare for potential hazards doesn’t take away from the excitement in the moment). The 107 miles of NET trail in CT contain some of my favorite sections of trail I have ever walked.

Here are my highlights:

Bluff Head

Bluff Head is just 30 minutes from Downtown New Haven and after a steep climb, you will be greeted with a trap rock ridge full of stunning views to the east. On my NET thru-hike, this section provided the first overlook views of the hike. Locals can turn this into a nice 7.3 miles loop with almost 1900 ft of elevation change.

* While stick season is my personal favorite time of year to hike because of the unparalleled views of far-off ridgelines, I imagine this section would be even more beautiful during fall foliage.

Chauncey Peak

Chauncey Peak has everything you want from a hike. The well-maintained trail was fun, and the strenuous (and occasionally technical) climb was rewarded with stellar views of Mount Lamantion, the Reservoir, and of Hartford in the distance.  Just 21 minutes from downtown Hartford, locals can tackle Chauncey and Lamentation in one 3.7 mile loop that contains almost 1000 ft of ascent.

*When I got to the summit of Chauncey I was completely blown away. Migratory hawks were soaring around my head as I stopped for almost an hour to eat and take in the views of Lamentation Mountain and the Hanging Hills in the distance.

Castle Craig

Coming upon Castle Craig while hiking is an experience unrivaled during the CT section of the NET. It was by far my favorite experience during the first 107 miles of the trail – finding out that this random Castle on the edge of a Connecticut cliff was a monument dedicated to the Hanging Hills being the tallest spot within 25 miles of the USA’s eastern shore was just a bonus. From my perch beneath the Castle I could see all the way back towards the Long Island Sound and got a great peek at the ridgelines I would climb throughout the rest of Connecticut. The best part about the Castle is that it doesn’t have to be a hidden gem. It is just 30 minutes from both New Haven and Hartford – putting it within a half-hour drive for almost 2 million people.

*From Chauncey Peak, I assumed this was just a fire tower. I was delighted to find Castle Craig instead. The Castle is made out of all local trap rock and blends into the landscape surprising well.

*I had to include a panorama of the Castle. You could see for miles to the west, north, and south. A picture can never do a view like this justice so I encourage everyone in New England to take a day trip sometime.

My Takeaway

The NET is unlike the other 10 National Scenic trails. It passes through bustling suburbs and by major metros for a significant portion of its length. While at times I found myself wishing for the pure wilderness experience one can find in the West or North East, the NET has enlightened me to how wild the areas in between the busiest of manmade landscapes can be. This experience has encouraged me to find adventure and nature wherever I find myself in the future – whether it be the MA section of the NET, my own neighborhood, or a major city.


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Comments 3

  • Cody Hodney : Apr 21st

    Hey Jacob!

    Im leaving to thru hike the NET on May 1st. I just had a few questions about the trail if you didnt mind answering a few! First off how was the camping situation? I know its not full of campsites but was it stealthable? Also, how were the river crossings? Im trying to figure out a way to get past the CT river without driving or walking all the way around. Any other info you have would be helpfull. Hope to hear from you soon!

    Cody Hodney

    • Seth Winkleman : May 9th

      Where is the 7 mile bluff head trail?

      • John Muise : Apr 10th

        Trail head is a few miles south of Durham CT on rt 77. Small but adequate parking lot.


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