Courtland Ave. is a great area of Bridgeport. The people that live in Black Rock LOVE living there and have their own little community. The Black Rock Art Walk occurs monthly during the warm months and it is well attended. (
index) I am not sure if it is happening this year but I would expect it to. If you can make it out to some of the events, it would be a good way to meet people living in the area and to meet the shopowners. There is very little crime in the area and St. Mary's is gorgeous before jellyfish season arrives--then you can expect the Sound to look like a horror movie for a few weeks.