rnine
You have to know the secret for finding the trail head on a dirt road running across the ridge. About a 20 minute level walk after the unmarked parking lot meets with the Appalachian Trail where you turn left to join. After a while of climbing you begin to see the view including Twin Lakes CT. During the right time int he summer (July?) look for wild blueberries near the summit.
Norey
Bear Mountain is the highest peak (not point) in CT. A great 6 mile hike is from the Undermountain Trail off Rt. 44 in Salisbury. You take the Undermountain Trail to the Appalchian Trail North up Bear Mountain with its great views of the Berkshires. Keep going north to the Paradise Lane trail that will take you back to the Undermoutain trail and back down. Truley a classic New England hike