Middletown

88 reviews

This is one of my favorite hikes in CT. It's only 10 minutes south of Middletown but when you're on the trails it feels like remote New England. The paths are beautiful with a photo-worthy view around every corner. All of that aside - if hiking the full 10 miles from Bear Hill to Seven Falls and back - it is legitimately rated hard.
1. Make sure you wear hiking boots for this. Many places on the trail you are traversing various grades of granite. Some mildly steep, some very steep and in three different places there are near vertical 8 - 10 foot scaling. Several of these places my dog would not have been able to get up or down - and she is a very athletic border collie.
2. Several people reference the intersecting trails. There are 4 main places and several minor where I hiked into an intersection with 3 or 4 path options. While I had this app and I was also recording my progress on map my hike, that still didn't prevent me from choosing the wrong path sensing I was headed in one direction only to look down at my apps 50 feet down a path just to realize I was heading back the way I came. I finally broke out my old school compass given the frequency that it happened.
3. The blue-yellow trails are far easier than the straight blue trails. If you have a dog or younger kids you will probably be safer staying on those trails.
4. Definitely wear and bring bug spray with you. What makes this hike so pretty in many places are the springs, creeks and bogs. But with water come a lot of bugs even early in the season when it's still cool. I wore a lot of bug spray and reapplied several times so they were not an issue.
5. This entire area is breathtaking when the mountain laurels are in bloom.