I loved living in CT, but it was many years ago. I lived in New Canaan, which is very wealthy. I rented a small house on a large estate, so I was one of the poors. It was a long walk to the train, but there is a train to NYC, and I went in a lot, even though I didn't work there. I could never afford to buy a house in New Canaan, Greenwich, Darien, etc. You have to move out of commuting distance to NYC to get a house that's moderately affordable. Property taxes are pretty high in CT.
Lots of CT is very rural and pretty. It's also somewhat poor. The NY suburbs raise the average income, but NE Ct is very insular and you can get a very nice, cheap antique house there for not a lot of $$, but there's nothing to do, and I, for one, would be miserable there.
Litchfield County, where I lived briefly, is beautiful. It would be a nice place to live if you had a remote job and wanted to go into NYC once a month or so. There are cute restaurants and stores, and lots of stuff to do, especially in the summer. But real estate is quite expensive there.
The shore is quite pretty too, and quite expensive, but as you go inland, the prices drop. Hartford is a gritty city, as is Waterbury, Danbury, New Milford, New Haven, Bridgeport, New London. Any largish metro area is rather run-down, at least they were the last few times I visited.
Are you moving there, OP? If you have lots of money, you'll be fine living on the coast or the NY suburbs. Otherwise, it's not the greatest state. Middletown is nice because of Wesleyan University. UConn is in Storrs, but I've never been there, so don't know the town. Yale doesn't really upgrade New Haven that much. There's loads of cuteness in the rural parts of the state, combined with provincialism.
It's cold in the winter.
I might move back there if I had to, but I wouldn't enjoy the winters. Otherwise, it's pleasant enough if you aren't too far from civilization.