The tallest mountain in Connecticut is Bear Mountain. On the Appalachian Trail, that is. Connecticut Route 41 is the main access route. .
The Pachaug is Connecticut's biggest state woodland. The large, continuous block of forest with numerous paths running through it is in the southeast corner.
Very wooded, typical Connecticut trek, with Chapman Falls nearby and lots of cool bridges. It offers some decent vista vistas.
It is 165 feet tall and has fairly cool architecture. You can see into New York, Mohonk Mountain, Springfield, Massachusetts, and Hamden when it's open and you ascend to the top, but you also get some fairly commanding views.