Climbing to Connecticut’s Highest Point

Climbing to Connecticut's Highest Point.

Climbing to Connecticut’s Highest Point

Ever since I was first introduced to the world of hiking a few years back, it has become an obsession of time. I find myself craving more time outdoors, taking time to enjoy nature and climb mountains whenever possible.

Round Mountain

Most recently, I’ve attached a goal to my love of hiking: to hike to the top of all of the high peaks in the United States. Any chance I have a free weekend, I find myself looking up potential road trips to states nearby in hopes of hiking to the highest point of each one. Last weekend, it was all about climbing to Connecticut’s highest point.

What’s most interesting about Connecticut is that its highest point and highest peak are on two different mountains. The highest peak is Bear Mountain, but the highest point is on Mount Frissell, a mountain whose summit is in Massachusetts. That leaves Connecticut’s highest point directly on the border between the two states.

State Line

Early Saturday morning, a few friends and I hoped in the car and headed two hours north. Driving past rolling green fields, patches of sunflowers, and the occasional farmhouse, I immediately fell for the areas of New York and Connecticut that we were driving through. It was peaceful and full of natural beauty.

After driving through the quaint town of Salisbury, Connecticut, we turned onto Mt. Riga road. It was a normal paved road, that eventually turned into an unpaved one. At the end of the road, there was a damn, and we turned right, following the road until we reached the AMC parking lot.

AMC Parking Lot

AMC Parking Lot

We parked and headed up toward the state line marker on our on our right, and on our left was another small parking lot and a gravel path marked with red trail blazes, the trail that would lead us to the highest point in Connecticut.

State line marker

After my last hike to the highest point in New Jersey, I was worried that the trail would be overgrown and buggy. But, as soon as we started on our way, I was pleasantly surprised. Instead, it was clearly, and even though it was rocky, it was a mild day and there were no bugs to bother me on my hike.


Eventually, we came to our first scramble, one of many on the trail. Even though in my mind, I tend to dread a scramble before I get to it, they always wind up being my favorite aspect of a hike, as they tend to change things up a bit. I love being able to really use my body in different ways to make it up to the top. Plus, they tend to break up the monotony of continuous walking and add a challenge, even though the scrambling on this trail wasn’t difficult or technical.


After climbing up a few of these, we eventually reached the top of Round Mountain. Here, we took time to enjoy the views, but were a bit confused as to where to go, thinking we were close to the high point. Instead, we eventually discovered a trail blaze and continued on our way.

Carin on top of Round Mountain

View from Round Mountain

We headed down off Round Mountain and then scrambled up Mt. Frissell, following the red blazes. Here, we reached an outlook that offered views of green mountains and a lake, along with an abundance of grey clouds.

View from Mt. Frissell

A little further up, we reached a cairn that marked the highest point in Connecticut, along with a border marker, and a container with a notebook for people to write down that they had made it to the high point.

Connecticut's highest point

High point marker

Marking down my accomplishment

There was no real view here, but the excitement was not in the view. Instead, it centered around reaching my third high point. We encountered others on the trail, who were reaching their sixteenth or twenty-fifth high point, and this just inspired me to keep on going. Three high points may not be anything exciting, but the feeling of having three down is enough to motivate me to keep on hiking and going after my goal.

Pathetic Jumping Shot

Full of adrenaline and excitement from reaching the high point, we easily made our way off the trail and back to the car. Then, we celebrated in town with burgers and a cocktail before hitting the road again. It was an easy day trip from Northern New Jersey, and it was nice to escape to the country and mountains for the day.

The Boathouse

This weekend, I’ll be tackling the high points of Massachusetts and Vermont, crossing two more high points off of my list. While I’ve been to both states before, I can’t wait to see another side of them by spending some significant time in the mountains. Stay turned on Instagram and Twitter for immediate updates of my progress.

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Comments (5)

  1. Kevin

    Beautiful photos! Makes me wanna go!

    1. The World Wanderer

      When you come to the East Coast, we’ll do a trip! Maybe in the spring. It’s a quick day trip. 🙂

  2. Francesca

    I love this adventure and these goals you’ve created! Only three high points, you say? Pffft. That’s three more high points than I’ve achieved! Even though it makes me sad that I haven’t been hiking in so long, I think it really is a unique way to see more of our country.

  3. Fiona

    Great achievement, congratulations! Hiking is not something I have much experience in but I would love to get more involved – Ireland has such beautiful trails, so I’ve no excuse really!

  4. Traveling Ted

    I have hiked the highest point in Wisconsin. The hardest part was finding the park in my car. Also, I hiked for 4 miles on the Timm Hill trail and realized the trail was actually like 8 miles from Timm’s Hill, so it was kind of a debacle, but I finally got there. I do the same thing any time there is a sign in book and put my website 🙂 Congrats on marking another peak off your list without oxygen and sherpa.

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