I would recommend the Old Saybrook area and environs (Chester, Essex, Deep River, Clinton Westbrook, Old Lyme). It is pretty much half way between Boston and New York (2 hour drive to either one). It's on the shoreline so the weather is better all times of the year. The Shoreline East connects to the Metro North to go to NYC as well as Amtrak connecting to both NYC and Boston. Bradley airport is about 50 mins. There is plenty to do, there are some great restaurants in the area, if you are boaters there are lots of opportunities.

Those Connecticut shoreline towns are charming. And, like all seaside towns, offer expensive real estate.

Small town/ rural feel, not far from interstate and truly half way between NYC and Boston would be Durham, CT. It's a beautiful small town with a real country feel but not too far from CT's cities and shoreline. Nice homes there, too.

Western CT usually gets more snow than the rest.

Ahhh, and Lyman Orchards nearby!

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