Chester is adorable and has some great food and a brewery. You could see a show at Goodspeed and also check out Essex or Guilford centers. You could also stop at Fox Farm on the way from Lisbon. Grano Arso in Chester would be a great special occasion place. Madison Beach Hotel for drinks on water and then Bar Bouchee would be really nice too.

In New Haven, you could do an art museum trip, see a show, and a really nice dinner at somewhere like Olea, The Luke, Union League, Tavern on State, Fair Haven Oyster.