Since I haven ' t lived in the area for about 20 years you can take my opinion w a grain of salt . Danbury is probably going to have your most culture . It has a great downtown area with a handful of bars restaurants and even a summer concert series . The Danbury Mall will probably be your goto place for shopping em masse plus there are plenty of bars other places to eat in the Danbury area . My family loves Rosie Tomorrow ' s . WSCU routinely puts on shows by bigger bands and I think there is a more ' local ' theater on main streetit was a movie theater when I was growing up but has been revamped since then . In High School my best friends lived in Brookfield . We did a lot of stuff that teenagers would do but can ' t really comment on bars fine dining in that area . Ridgefield has a niceish theater Ridgefield Playhouse but will probably be one of the more expensive places to live . I saw Soul Asylum there a few months back it was a cool venue . Newtown used to have a ' dollar ' movie theater in the town hall . No idea if they still do that . I can ' t comment too much about the other towns but if you ' re looking for a better bar scene I ' d rather take a trip to Hartford New Haven on a weekly basis during nonrush hour than have to drive through CT during rush hour .