We like Litchfield County and have many friends with homes here. The county has a history of resisting development and preserving historic land and architecture. We like this. The conveniences are there, but somehow, tastefully done. If we ever need the big box stores, Torrington is not too far away, but far enough. We love the easy commute from New York City by train (Metro-North, Wassaic), which is a huge plus for a family with a many-layered schedule. The drive up from New York is very pleasant. Its not a parking lot on Fridays, like roads leading to the Hamptons.
The movie house in Millerton is a great place to see new releases, with two screens that are generally 'one for the kids' and 'one for the adults'. There is a great topographical diversity to the landscape; the Housatonic Valley, the lakes, the rolling farmland that suddenly reveals breathtaking vistas as you pass through it.