This Is the Most Claustrophobic Hike in Connecticut—Would You Try It?

One of the things that always impresses me about Connecticut is how much there is to explore, and just how many surprises there are within one of the smallest states in the country. Far away from the state's beautiful coast, you'll find Cockaponset State Forest, not far from Middletown. This beautiful natural getaway is home to over forty unique trails, one of which has a big surprise. Known as the most claustrophobic hike in Connecticut, the Chatfield Trail will take you into the great unknown. One of the more challenging hikes in the park, it's the ideal adventure for a brisk fall or winter day when you want to see nature at its most peaceful. Just be prepared for quite a squeeze.

That's because the Upper and Lower Chatfield Trail is home to one of the most unique geographical features in all of Connecticut. When I saw pictures of this part of the trail, I almost couldn't believe it—but there are plenty of people going inside it every day! So strap on your hiking boots, pack some extra courage, and discover one of the most mysterious and beautiful locations in the Nutmeg State.

Spanning 7.6 miles, the Upper and Lower Chatfield Trail is an out-and-back journey that takes you through some of the most beautiful terrain in Connecticut. You should expect to encounter plenty of uneven terrain and an 853-foot elevation gain along this challenging trail.

This hike is beautiful all through the year, but especially in the fall. Keep an eye out for small waterfalls as you pass by creeks, and the impressive rock formations that dot the path, hinting at just how ancient much of this terrain is.

When you reach the largest rocky cliffs on the trail, believe me, you'll know it. This is one of the most impressive natural landmarks in Connecticut, and makes for an amazing photo op on its own. You can stop here and enjoy a fantastic hike, but if you're daring, keep your eyes open.

There is a small crevasse in the rock, given the irreverent nickname "Fat Man's Squeeze". It allows you to weave your way in between the rock walls, exploring an area of the trail that few people do. This rocky terrain might definitely be claustrophobic, but it's one of the most unique hiking experiences you can have in the Nutmeg State.

Have you braved this claustrophobic hike in Connecticut and managed to get yourself inside its rock wall? If not, tell a friend about this article and plan your adventure within the boulders! You can see more photos of the trail on the official AllTrails trail listing. While you're here, you're not far from Middletown, one of Connecticut's best winter towns. It's also a great opportunity to visit the Red Fox Restaurant, one of the state's most romantic dinner spots.

If you're new to hiking and want a little backup on the trail, we highly recommend a subscription to AllTrails +—this app-based hiking tool will make sure you're always in the loop, keeping tabs on your progress and giving you point-by-point directions. And if you want some more ideas for how to spend your time in the region, why not let Only in Your State's AI-powered travel planner ask you a few simple questions about your trip and give you a customized travel itinerary?