Hiking Connecticut: A Relaxed Day on the Trail | Day 102 (2026)

Day 102: A Hike Through Connecticut

Today was a day of rest and recovery after back-to-back 25+ mile days. I woke up late, around 7 am, and hit the trail around 8:30 am. My slow start continued as I needed to get water immediately, and I only made 0.5 miles by 9 am.

As I entered Connecticut, I felt a sense of relief. The day's hiking started easy for the first mile, but then a climb over the next couple of miles awaited. I hit the Connecticut border, entering my 10th state on trail! My new shoes, while comfortable out of the box, caused some discomfort in my feet due to the break-in period. I took a relaxed pace, knowing that our plan today was less ambitious, just 20 miles with a HERO in and out of Kent, CT.

About 4 miles in, I reached a river that the trail followed along. I spotted Shooter soaking his feet in it, and we decided to join him. We took a 15-minute break to soak our feet in the cold river water, which was a nice respite. We hiked along the river for a blissful and calm mile, then took a short blue blaze to check out a covered bridge just off trail, which was a cool diversion.

Back on the trail, we were greeted with a relatively steep climb of 700 ft in less than a mile. I lost my balance and fell over into some brush, which hurt nothing but my pride. After reaching the top, I enjoyed a nice view of the surrounding countryside while chatting with a couple of day hikers. The next couple of miles were pretty flat, with just minor ups and downs.

The last few miles into Kent featured two steep ups and downs, which I trudged through slowly and methodically. I even saw a snake at one point! Once in Kent, we made our way to a convenience store for some cold drinks to help hydrate us before heading over to the outfitter.

We arrived at the outfitter right after they closed, but it didn't matter as we didn't need anything specific. We just wanted to check it out and maybe leave our bags there. On we continued to our next stop, food. We decided to go to Cozzy's on Main, which served burgers and pizza, what we were most interested in currently.

Cozzy's was pretty good! We were able to bring our bags inside, charge electronics, and the food was really good. I got a 14-inch Bacon, Cheddar, & Ranch Pizza and some garlic knots for the 3 of us to share, and it all got demolished! After dinner, we headed over to the grocery store to resupply with a couple of days worth of food and then headed back to the trail.

We wanted to get to the Stewart Hollow Brook Shelter before dark and we just made it in time. Although once again, we were setting up in the dark. The hike went well enough, especially since some of it went right along the Housatonic River, a lovely backdrop to an evening hike.

Day 102 Stats:
- 20.3 miles
- 4,429' ascent, 4,731' descent
- Wiley Shelter to Stewart Hollow Brook Shelter
- 10 DSLC
- Times stove has been used: 14
- Snakes Seen on trail: 24
- Whole Pizzas consumed Tracker: 14

In my opinion, this day was a perfect example of how hiking can be both physically and mentally challenging, but also incredibly rewarding. The sense of accomplishment from completing a long hike, even with some discomfort, is unparalleled. The beauty of Connecticut's countryside and the camaraderie with Shooter made it all the more special. I can't wait to see what the next day brings!

Hiking Connecticut: A Relaxed Day on the Trail | Day 102 (2026)
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