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Not to be difficult, but "best towns" for what? For walking? For restaurants? For art/culture? For food shopping? For non-food shopping? For natural beauty? For closeness to hiking and nature reserves? I think each of those questions have different answers. Westchester is huge and there is tremendous variety in the types of towns you can find here, from old suburb to new suburb to rural.
Not to be difficult, but "best towns" for what? For walking? For restaurants? For art/culture? For food shopping? For non-food shopping? For natural beauty? For closeness to hiking and nature reserves? I think each of those questions have different answers. Westchester is huge and there is tremendous variety in the types of towns you can find here, from old suburb to new suburb to rural.
Sorry...I should have been more clear. I would like a relatively affluent, but not ridiculous community, with a close knit feel, a nice downtown, and good schools. Proximity to the water is a plus, but not a necessity. Proximity to a train is the same.
I am more familiar with northern Westchester, so I'll stick to that. Croton would seem to fit your request: affluent but socio-economically diverse and not at all "uppity", nice village, strong sense of community, good schools, on the water. And it has a MetroNorth station. Katonah is more affluent and less socially diverse, but otherwise fits the bill (but no water).
haha this thread is pretty funny since ive been looking to leave my town of mt pleasant for about a year. Overall, westchester is a good place to live in terms of safety, schools, etc. Taxes are high and the people can get pretty annoying. Areas in southern westchester (yonkers, mt vernon.) are typically cheaper but a bit rougher though they do have nice areas. Areas like harrison, rye, scarsdale, pelham, and chappaqua are more expensive with nice houses but somewhat snobby people. My town (mt pleasant) is one of those typical small town USA situations while areas north of white plains tend to be a bit more isolated and lack urban qualities. Basically, westchester offers everything from big cities (white plains) to small towns and everything inbetween. However, just be sure u can afford it and look for what type of enviornment u enjoy along with the right type of people.
Not much to go on as to what you really are interested in. So here is a generalized break down of towns that might fit some of your needs.
Having lived in both areas...
If you are coming from Garden city and prefer North Shore style living then you probably would be most interested in Bedford, Katonah, Somers and parts of Mt Kisco (towards Byram Lake) if you are looking in the northern end of Westchester. All will be close enough to trains, and have a somewhat community feel. Much of the towns have large swaths with more of the estate look of North Shore LI. Central Westchester has Chappaqua (where the Clinton's have a residence) and North Castle especially towards Armonk. Southern Westchester has Scarsdale, Mamaronek and Larchmont. IMHO the "water" isn't much of a feature in southern Westechester with the exception of a few fairly high price places... you'd be better off seeing the LI Sound from LI. Along the Hudson you may find a few places fit your needs, like some parts of Dobbs Ferry and Ardsley.
It isn't much of a drive from LI to most of Westchester. You might want to just take a few 'day' drives to check out the towns to see what appeals to your North Shore taste.
I think most comparable to Garden City would be Bronxville, Rye, and Larchmont. Great areas, but very pricey. All close to city and nice villages with good shopping and great restaurants.
Bedford/Pound Ridge/Armonk (even Chappaqua) however, do not have as large of a nice downtown shopping area as Garden City does.
True, but Mt Kisco does and it is next door. All these towns are less than 10 minutes apart. Personally, the quality of your closest town isn't really important, what matters is that you can easily get to one or more towns that you like. I go to about 4 different towns on a regualr basis, all less than 15 minutes away and all with different strengths and weaknesses.
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