for wilderness area, i enjoy hiking bear mountain. aparently its the highest peak in CT, but there is another mountain that starts half in ct but peaks in mass.
good hike, depending on which way you guy up and down, it offers a fair amount of versatility in terrain. there is plenty of steep rock scrambling (not fun after the rain!) and there is alot of gentle sloping walking. beautiful area any season.
as for gear; i don't buy that much gear anymore, i have collected what is my set for quite some time i think. but when i was buying, i looked at hardware stores for knives and they usually have some stuff in a little camping section. Dicks, Cabelas (i have heard, never been. soon to change i hope), walmart has some stuff, sometimes you have to look hard to find the quality stuff.