anywhere on the southern coast and you can take the train into NYC if you want for actual night club night life. Stamford, Norwalk and New Haven have more nightlife within CT than other towns. Norwalk you can take a train up to Wilton, Ridgefield or Bethel and that would be more down to earth CT "real America" compared to all the towns on the coast. If you had a car you could go further north into the state and see the woods, rolling hills and landscapes that make the state a treat. These towns have the small downtown town centers with shops and restaurants and then the town branches out from there. Kind of like ant hills. Also, if you can come in the fall, you'll catch the fall scenery.