Re: Housatonic river, CT
It has been awhile (think 1985) but I fished right where you are talking about. I did not have a guide and I caught several trout. The river is quite wadeable unless there has been some significant change. This is a wide piece of water and you should be well off fishing dry flies there. A typical Eastern Dry Fly selection should be in your possession before you put on your waders.
Check for a local shop online to get the lowdown on what to tie. Great and Historic little town Cornwall Bridge, good café's (best mushroom soufflé' I've ever had) and interesting shops, you will enjoy it.