I lived there for 12 years, 84-96. You will like it, great places and only 50 minutes out of mid town. Realize that Fairfield county is affluent for the most part, so I would be very surprised for economic and demographic reasons if a good pool hall would work.
When I was there a place existed in DT Stamford north of the main town square. Look to the towns in NY towards the city and also in 30 minutes you are in the Bronx or Queens. Going north, Bridgeport but the same travel time you would do better towards NY.
Good luck!
BTW:
Colony , it is a bar in Stamford that serves one food item.....Great, outstanding, thin crust, tangy, Pizza. Regulars call it Jimmy and BoBo's. Since we moved in 96 I wanted my wife to go back, work there and lean the formula to make their pies!