New Haven, CT has lots of arts, culture, dining, cool architecture, great live music scene. Just made NYT “best places to visit in 2023 list”. The casinos in eastern CT (Mohegan, Foxwoods) are fun. In the summer, RI shoreline is lovely, highly recommend taking the ferry to Block Island and renting some bikes or scooters (limited cars on the island). Providence is another cool small city, with dining, arts, music, etc.