Border areas can be tough - so it pays to look in both areas. I know nothing about New York records, but Fairfield County records are held at the town level - even back to the 1700s. However, vital records up to 1850 have been compiled into one state-wide database called the Barbour Collection or Barbour Index. It is widely available at any library with a sizeable collection of New England material and is available through your local FHC. Also, in recent years the collection for each town is being published (they were doing a couple of towns each year in alphabetical order, but I don't know what town they are up to now). But they might be available through interlibrary loan.
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