One of the best experiences I ever had was at Boiling Springs in 2001, I saddled up to the bar and drank about 15 glasses of beer watching the Stanley Cup Finals, the bartender kept filling up my glass, filling up the pretzels, etc...he stayed open late to let the game finish, then charged me about $18 haha, I threw $40 down on the bar and still made out like a bandit. Then crashed on the lawn of the B&B for $1...resupplied the next day and headed out. Great time.
CT is a pretentious state, no question, full of money and people who have money - which can SOMETIMES mean arrogant or unfriendly people, especially towards hikers. I have only hiked CT once and had no issues myself.
As for the best town...Hot Springs all the way. Damasus is nice, but Hot Springs wins any day for me! The only thing Damascus has over Hot Springs is the supermarket.