[kristiv]

Another option to New York City from the Ridgefield or Redding area is the shuttle that operates out of Ridgefield and takes commuters to the Katonah station. The shuttle leaves from Jesse Lee Methodist Church in the middle of town, makes one stop in South Salem and then meets the major commuting trains in and out of Grand Central. You can see the schedule at MTA Home Page if you go to the station information for Katonah (on the Harlem line). My husband does this to mid-town on a daily basis and it takes him about 90 minutes door to door from our house in central Ridgefield. Although the shuttle does not meet every train if a commuter needs to come home early or late the Housatonic Area Regional Transit Authority grants two taxi vouchers per month so they get you back to your car.

[notjustamom]

Are you looking for something rural, semi-rural, or with lots of shopping? Fairfield is nice, but it's really like a small city to me, nothing like New Canaan/Ridgefield/Wilton. It really depends on what you are looking for.

My IL's bought their home in New Canaan back in the early 1960's. At that time, NC was not considered a desirable location to many, because it was thought of as too rural. They bought their home on five acres for a ridiculously low price, my current car cost more than their home did! People who have lived in NC for that long tend to be very laid-back and down-to-earth, not snobby at all. The town sort of evolved around them. So I'm not sure I would classify NC as entirely "old money", since so many people we know there have "new money", it's a mix of both. Greenwich is more of an "old money" town. NC is a wonderful town to live in, though. Excellent schools, nice parks, the center of town is village-like, and the commute to NY is not bad at all.

Editing to ask, have you considered Westport?
Westport, Connecticut - Wikipedia, the free encyclopedia

[CathM20]

What about Stamford? In my experience those who are new to the area with commutation in mind, do not want to live further north than Stamford if there will be a fairly regular commute to NYC. It is about a 45 minute ride by Metro North to Grand Central. However, it does depend on how often the commute is to NYC vs. Rhode Island. 06903, the North Stamford zip code has been deemed the most affluent zip code per capita in the US! Not only does Stamford have shopping, great restaurants, theatre, art, etc., but Stamford also has diversity, education and is growing by leaps and bounds - no snobbery here! Yes, Trump Parc is going up, as well as Highgrove, an upscale urban condo with homes starting at about $1.5M. There are plans to built up Stamford's Mill River area and the South End leading to more waterfront homes/shopping, etc., sure to increase home values. Royal Bank of Scottland (RBS) has begun construction, and RBS (not UBS) will have the largest trading floor in the country. Let me know if you would like more info on Stamford!

[CathM20]

P.S. Westport is also fab!