Anything south of New Milford or Kent is Fairfield County. Also southeast of New Milford is mostly Fairfield County. Even Sherman which is in the southern Litchfield Hills is part of Fairfield County, although most Sherman kids go to New Milford High which is not part of Fairfield County. Shelton is also part of Fairfield County, yet Shelton does not play sports in the FCIAC, plays in SCC. Though many years ago there was some talk of Shelton High joining the FCIAC, not sure why it didn't happen.you aren't the only one. typically people think it's just Stamford/Westport/Greenwich/Darien/New Canaan when it comes to fairfield county football