Greenwich CT? I would estimate that Bradley is not more than a 2 hour drive, possibly less, and not too much traffic. I'm not sure if you would take the Merritt to hook up with I-91 North. You could try Mapquest or Yahoo maps and check out the drive/distance.
I have two daughters from my first marriage -- 13 (7th grade) and 10 (4th grade). 3 years ago, I married a man who has 3 kids -- a 20 year old who lives in Western Michigan and visits on occasion (the only non skiier/snowboarder), a 13 year old girl (who has been a close friend of my 13 year old since birth so I've known my husband and his 2 kids from that marriage for 13 years) and her 11 year old brother. They live in Cincinnati with their Mom and step-dad and baby brother, and spend summers, vacations, and long weekends with us, so we know Bradley airport very, very well (it's an easy in and out airport and parking's not too expensive). My house is a constant flux of kids in and out as my girls live almost half-time with their Dad in the next town, so we have time with no kids :D and time with various combinations of kids that changes all throughout the year. When we are all together, it's a trip! Since I'm a divorce lawyer/mediator and parenting coordinator by profession, I coodinate the kids' schedules with all the other parents and we all get along pretty well I must say.
The four younger kids started snow sports in the 05/06 season -- my 13 yr old daughter and my 11 year old (step) son board, my 13 year old (step) daughter and my 10 year old daughter ski, and this past season, they all started moving onto the blue trails and getting better. Soon they'll smoke me and the snow boarders are following me into the terrain park now.... I'm just trying to stay ahead at this phase so I can keep up in a few years!