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We are a family of 5, mom, dad, 3 boys ages 11, 9 and 7. We are relocating from the western suburbs of Chicago to Fairfield County. We have a good housing budget (1mm to 2mm) -- but we're midwesterners, so we want good schools, friendly people, great community amenities and a minimum of snobbery. We love Westport aesthetically, we like Fairfield. My question is, where is a "normal" midwestern family going to feel more comfortable and have the most stuff for their kids to do -- Westport or Fairfield?
We are a family of 5, mom, dad, 3 boys ages 11, 9 and 7. We are relocating from the western suburbs of Chicago to Fairfield County. We have a good housing budget (1mm to 2mm) -- but we're midwesterners, so we want good schools, friendly people, great community amenities and a minimum of snobbery. We love Westport aesthetically, we like Fairfield. My question is, where is a "normal" midwestern family going to feel more comfortable and have the most stuff for their kids to do -- Westport or Fairfield?
Both towns are wonderful for families and your budget allows you much flexibility in your search. The schools in Westport will be a step higher, but Fairfield's are still excellent. As for friendly people with no snobbery - well there are snobs in both towns. Westport is wealthier and less diverse, so many would suggest that Westport is more pretentious. There is a lot of new money moving into Fairfield with that attitude as well. It's hard to stay away from pretentiousness since you're moving to one of the most affluent areas in the nation, but you will still find many modest and down to earth folks in both towns.
Have you looked into Ridgefield? I'm not sure where you and your significant other will be working, but Ridgefield is a very family oriented, non-pretentious community in northern Fairfield County. It's more rural than Fairfield and Westport but does have everything else you desire. You can get more for your money here as well.
Your budget also allows you to access other Fairfield County towns, such as Darien, Wilton, New Canaan and Greenwich, but you will only get a modest home in these communities for $1m. All incredible towns, but are some of the priciest in the country. Greenwich is often referred to as the "Beverly Hills of the East Coast."
If you aren't interested in expanding your search, then I think you should consider Fairfield. Westport is an incredible town but it seems you're not looking for that 'high end' feel which many in Westport desire. Fairfield has more of a middle class flavor and is an excellent town to raise children. It's one of the most desirable towns in the nation - search "Fairfield" in the threads and you will see.
I see from your posts that you have also considered Indianapolis. While you can get more for your money in Indiana, that area is less progressive (which I see you stated in an earlier post) and the economy in Indianapolis unfortunately isn't as strong. Fairfield County has a number of Fortune 500 companies and even during recessions, CT usually comes out OK (knock on wood). You're close to NYC, Philly, Boston, Providence (plus the beaches of RI) and the mountains of upstate NY, VT and NH - all places you can day or overnight trip to.
All in all, you can't go wrong with any of the towns mentioned. If you have more questions, feel free to ask.
Last edited by kidyankee764; 05-13-2008 at 11:29 PM..
Your budget should buy more in Fairfield then Westport-
that being said I would not expect a 'Midwestern fuzzy and warm feeling' in either place.
Kidyankee suggested Ridgefield, which is perhaps a bit less pretentious and more friendly.
Generally speaking in most of Fairfield county you may encounter a sort of aloofness that at first you may take as snobbishness- some of it may be- but many people here seem to live in a detached world of their own.
Indianapolis would certainly be somewhat closer to what you are looking for in a friendlier Midwestern attitude, but again as suggested above is far less progressive on social issues which may not suit your needs. And economically is not as strong. Additionally Connecticut lies in a far more favorable geographic location- near New York, Boston- Vermont, Cape Cod, great beaches, the ocean and more.
A final suggestion might be Trumbull not mentioned thus far- near both Westport and Fairfield, with a lower amount of 'attitude'. A most pleasant town, which may not have the 'marque appeal' of the others but where your budget will go much further then Westport, Ridgefield or Fairfield with less pretension and friendlier people then the other places mentioned.
Last edited by skytrekker; 05-14-2008 at 05:11 AM..
Westport is sort of like Beverly Hills east with a number of celebrities living there. It is still a very nice town with a lot of nice people and some not-so-nice people. Fairfield has a bit more diverse population since it has a wider range of housing options (everything from modest apartments to old money type mega-mansions). Fairfield is also a larger town than Westport so your chances of meeting people would be better. Fairfield is a really great town (both money Magazine and Ladies home Journal have said so) so I would have to say go with Fairfield. There are many beautiful neighborhoods in Fairfield, some (Southport and Greenfield Hill) I think that are nicer than Westport. If you like Westport's center better you could always visit it since it is so close. JMHO Jay
Thanks for the advice -- we are leaning toward Fairfield and in particular the beach area. Is that area OK? It seems like there are really grand homes and more humble homes all together, but that's kind of what we're used to. What's the reputation?
Thanks for the advice -- we are leaning toward Fairfield and in particular the beach area. Is that area OK? It seems like there are really grand homes and more humble homes all together, but that's kind of what we're used to. What's the reputation?
By beach area, do you mean Southport? Or near Fairfield Beach Road (Penfield Beach)?
You really can't go wrong in Fairfield - especially near the beach. The grand/humble mix is what I love about Fairfield. It's a nice mix of people all living in one area which keeps the pretentiousness to a minimum and the modesty prevalent.
Have you visited yet?
Quote:
Originally Posted by skytrekker
A final suggestion might be Trumbull not mentioned thus far- near both Westport and Fairfield, with a lower amount of 'attitude'. A most pleasant town, which may not have the 'marque appeal' of the others but where your budget will go much further then Westport, Ridgefield or Fairfield with less pretension and friendlier people then the other places mentioned.
This is another great suggestion - Trumbull is a wonderful town.
Just note that Trumbull is an inland town and does not have access to the beaches along Long Island Sound. Trumbull does have a couple of lakes with swimming areas and has a couple of public pools. I believe Trumbull residents can also purchase beach passes in Fairfield for a reduce rate (Not sure if this is still true). Plus Trumbull lacks a walkable town center like Fairfield or Westport has.
As for Fairfield, just about any part of town is good. The beach area was developed over the years with more modest homes. In recent years though, the area has been "discovered" and the newer homes are large and pricey. That is why there is such a mix there. This is a very nice area though. Jay
I would recommend Fairfield. Fairfield is far less pretentious than Westport can be--although I do love the look of downtown Westport as well as some of the homes and estates are simply gorgeous. Fairfield has excellent schools and has a great mix of middle-to-upper middle class and well-off to very wealthy people. A good mix. It is in a tremendous location in terms of beach access and is a wonderfully safe community.
One note about Fairfield that doesn't affect the town at all, but is something to be aware of: Bridgeport is right next door to Fairfield. Bridgeport has a few lovely neighborhoods, but for the most part, Bridgeport is a very unstable, blighted, slightly unsafe city. It's pretty ugly and blighted overall, as compared to the "fabulousness" of the rest of Fairfield County. It's Fairfield County's version of a "stepchild" really.
Some people care about that proximity, but most do not. I'd also recommend you take a look at Ridgefield (as someone mentioned) and New Canaan. If you want a bigger safe city with tremendous quality of life (although the schools are a couple notches below Fairfield's), check out Stamford. North Stamford has some of the best mix of estates, upper middle class homes, and seclusion that I've seen in the US. It's gorgeous and access to everything is 10-15 minutes away.
One note about Fairfield that doesn't affect the town at all, but is something to be aware of: Bridgeport is right next door to Fairfield. Bridgeport has a few lovely neighborhoods, but for the most part, Bridgeport is a very unstable, blighted, slightly unsafe city. It's pretty ugly and blighted overall, as compared to the "fabulousness" of the rest of Fairfield County. It's Fairfield County's version of a "stepchild" really.
This has been debated on this board before and I believe that Fairfield being located next to Bridgeport is not a problem. First of all, like any major city Bridgeport has its good areas and its bad. All of the neighborhoods along the Fairfield side of the city (Black Rock, Brooklawn and the North End) are very good. I fact many times you would not even know you have left Fairfield and entered Bridgeport when driving around the area. once I was driving out-fo-town friends around and they remarked how beautiful Fairfield was. They were shocked when I told them we were in Bridgeport. Jay
... but for the most part, Bridgeport is a very unstable, blighted, slightly unsafe city. It's pretty ugly and blighted overall, as compared to the "fabulousness" of the rest of Fairfield County. It's Fairfield County's version of a "stepchild" really.
Don't worry!
There are plans to construct a 10 foot high wall along the border of Bridgeport and Fairfield that will only allow those Bridgeport residents working as domestic help to enter Fairfield or Westport. Everyone else from Bridgeport will be banned from sharing in the "fabulousness" of Fairfield County.
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