Crossing Into New England: Beauty and Challenge on the Appalachian Trail
From Connecticut’s scenic ridges to Massachusetts’ rugged climbs, the AT reveals breathtaking views, historic towns, and unforgettable encounters along the path north.
Crossing into Connecticut, I was greeted by a sign proclaiming it the “Gateway to New England.” I felt at that moment that my journey was nearing the end, but little did I know I still had a lot of tough miles to go.
Though Connecticut only has 52 miles of the AT, it offers some of the most scenic views. The terrain here is relatively moderate, making it enjoyable for both beginners and experienced hikers. Highlights include Bear Mountain, the state’s highest peak at 2,300 feet; West Cornwall, with its scenic waterfalls; and Sages Ravine, a beautiful area known for its vivid fall foliage. Even in mid-summer, I found it to be one of the most beautiful stretches of the entire trail.
Connecticut also offers well-maintained shelters and numerous campsites, making it friendly to both section and thru-hikers. Adding to the charm are the quaint small towns that dot the trail as it winds through this lovely and historic state.
After Connecticut, I crossed into Massachusetts. At 90 miles, this stretch of the AT trail is almost double that of Connecticut’s and a bit more rugged. The ascents are steeper, and the terrain more demanding, but the payoff is worth it. Mount Greylock, the highest point in the state at 3,491 feet, delivers sweeping mountain views that make the climb worthwhile.
Among my favorite spots in Massachusetts were Bash Bish Falls, near the southern end of the trail, and Guilder Pond, a peaceful area teeming with wildlife. The state also offers solid infrastructure for hikers, notably Seth Warner Shelter and Shaker Campsite.
Not to be outdone by Connecticut, Massachusetts has several historic and very charming towns to visit while hiking the AT. One of my favorites was the town of Great Barrington, located in the heart of the Berkshire Mountains. The town is known for its thriving arts and theater scene.
Two things that I will always remember about hiking through Massachusetts in mid-summer are getting caught in intense and scary summer thunderstorms and seeing the largest rattlesnake I saw on the entire trail.
Connecticut and Massachusetts marked the start of my trek through New England, a region known for its beauty and the beginning of a tough section of trail. While these states challenged me physically, they also offered some of the most rewarding and scenic parts of my Appalachian Trail adventure.