Possibly moving to CT

Sounds like Greenwich or South Norwalk might fit that request. A dear friend of mine is raising her family in Greenwich and loves it.

I made the opposite move so I think I can provide some input but you will have to take it with a grain of salt! After 5 years of trying to see the good in the CT suburbs I finally gave up and admitted that I am not a CT suburbs person. I moved to the bay area for more affordable housing (isn't that what we are all looking for!), shorter workday, a shared expectation of work-life balance, more open-minded culture and schools, and better weather - and found everything I was looking for and more.

If you want to commute via train you really only have Greenwich and Stamford to choose between in CT, and unless your timing is perfect and you take the super-express express train its going to be at least a little over an hour on the train. Greenwich is very expensive and known for being very snobby, with very little diversity not an ideal culture for raising kids IMO but the schools are "good", Stamford is more affordable but has notoriously bad public schools, there are some magnet schools that I'd heard good things about but they are very hard to get into (lottery system), you can get a nice deal on a beautiful home in the woods in North Stamford but then your commute with drive + train will be over an hour and a half. Stamford does, however, have the world's best pizza (colony pizza, hot oil).

Have you considered NY suburbs like Rye or Larchmont that would be a little closer to the city and might meet your criteria? I don't know much about towns that aren't on the New Haven line but the NYtimes has a lot of good material on the atmosphere and appeals of various suburbs in the real estate section. If I were moving back to the NYC area myself I would probably look at the outer boroughs.

I grew up outside New Haven, and can say that generally, east of New Haven along the coast you get more liberal, academic, artistic communities, and west of New Haven along the coast you get more conservative, financial, business, corporate communities. The train to New York runs along the coast, and New Haven is less than two hours away. There are many lovely smaller towns. Closer to New York are the more affluent bedroom towns of New York commuters. Westport, Greenwich, Darien, New Canaan, Wilton, all have lovely pastoral settings and close proximity to New York. 

Schools will be much better.  The move from the east coast to CA has been hard for my academically minded kids. 

Hi,

Having lived there for 3 years I have to say that there are no towns in CT with a vibrant downtown. You should look into Wilton, Westport and Fairfield if you want good schools and easy commute to NYC. Or any town south of Fairfield really. Good luck, hope you find what you are looking for! 

Former Nutmegger with family still there. I agree that outside of the cities (which, except for Stamford, are not within an hour of NYC), there aren't many options for vibrant downtowns. It's pretty suburban. Schools are generally stronger and better funded than in CA (though sadly this is not a high bar!) but not as consistently strong as they once were, since the state has fallen on tough financial times in recent years. The wealthier communities have better-funded schools (but are generally taxed accordingly). For a commute under an hour, you likely want to look at the towns between Stamford and NYC on the New Haven Metro-North line--in CT, that's mainly Greenwich. (Be sure to look on the New York side as well--you may find better options there.) If you'd consider a slightly longer commute, extend this to Norwalk. If I were planning to move back today for a reasonable NYC commute with strong schools, though, I'd be looking in New York along the Hudson and Harlem lines--just something to consider.