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Appalachian Trail
As you enter New England, your mind is preparing you for bigger mountains like the Whites. But, most of Connecticut is easier than expected, just some rolling hills and lots of valley bottom trail along the Housatonic River. A few climbs are tough but do not last too long thanks to anti-switchback rules of the AT. There are several towns along the way that are easily accessible by walking to them, so you can get away with carrying little food if you have extra time.

One exception to easy mountains in Connecticut is Bear Mountain. See its page at:
Appalachian Trail - Connecticut
Bear Mountain Pictures
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Calebs Peak
Lions Head viewpoint
Summit of Lions Head
Entering Connecticut
Farm along the trail
Calebs Peak view
Trail goes through this narrow passage
Tenmile Hill sunset
Trail near Falls Village
Doing good
Giants Thumb
Great Falls
Great Falls
Trail along the Housatonic River
Bridge along the Housatonic River
Falls Village Hydroelectric Plant (see white blaze on power pole)
Crossing the Housatonic River in Falls Village
Housatonic River
Taking a break on Prospect Mountain.
Mountainside Cafe just a few minute detour off the trail.
The first half mile in Connecticut had some really nice trail work done.