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Hi,
We are visiting CT next weekend, and will be visiting Westport, Greenwich, Southport and Madison. The thread I started earlier recommended Southport and Madison, which I would like more info on before we visit. I've read that they are laid back beachy towns is that true? How are schools? Is there tons of stuff to do for kids between the ages of 7-13? Is it touristy during the summer? Any other useful information appreciated! Thanks!
Southport is actually a section of the town of Fairfield that straddles the Westport border. It's a beautiful little seaside village that is very expensive (but definitely within your price range). It's probably one of my favorite little towns in the state. Your kids would attend the Fairfield school system, which is very good (but a step below Westport's). I don't think I would call Southport "laid back", unless you're comparing it to New York City.
Westport is an exclusive town that is one of the wealthiest in the country, and is a haven for the rich and sometimes famous. It's known for being the (former) homes of Paul Newman and Martha Stewart. The schools are fantastic, though some would argue pressure cooker, and the downtown area very upscale (Tiffanys and the like). The town is really picturesque, dotted with marinas and yacht clubs along the shore, and country clubs lined with stone walls inland. In the past 20 years, it has become quite yuppified with large mansions and mcmansions being built.
Greenwich is a very large upper class town. There is Old Greenwich, Riverside, Cos Cob, Byram and what the locals consider "backcountry", which is where you'll find some of the most expansive and expensive estates in the world. Think tens of millions of dollars. Old Greenwich and Riverside are very nice little villages within Greenwich but, again, are very pricey. Byram and Cos Cob are the more "middle class" sections of town, where a small home can probably be had for $500k, especially in this market. Schools are very good. Backcountry is home to many, many celebrities. It is largely known as the Beverly Hills of the East Coast.
The above towns are all along Metro North's New Haven line, which runs from New Haven to Grand Central in Manhattan.
Madison is up the line past New Haven, and is more of a laid-back, beachy town. Schools are just as good as Westport, Greenwich and Fairfield, and you will get double the house for your money, or a similar home will be half the cost - however you want to look at it. It's only because the town is not commutable to New York City. It's also a large town land-wise, which means it goes pretty far inland where you have woods and lakes, and there is also a beautiful shoreline dotted with low-key marinas and restaurants. There is a very quaint downtown that is upscale, but less "exclusive" than the other towns you're considering. Madison is the type of town where you can walk around in casual wear and fit right in. Downtown Westport requires a little more "doing up", if you will.
Commuting to New Haven from...
Greenwich - If you will be commuting to New Haven on a daily basis and New York once a month or so, I would absolutely eliminate Greenwich from your list. It not only is very expensive, but it's a hike to New Haven on one of the busiest and congested highways in the country. It can easily be a two-hour trip each way, because you have to go through Stamford, Norwalk and Bridgeport, all of which are major employment centers. Then approaching New Haven gets very congested as well. The train would be an option, but that still would take about an hour, and getting from the New Haven train to the office might pose an issue.
Westport/Southport/Fairfield - Much easier of a commute than Greenwich. It will still likely take you about 45 or so minutes.
Madison - To get to New Haven, it will probably take you about 20 minutes. The traffic approaching downtown New Haven in the morning is not bad at all, and on the very worst of mornings, will only add about 5-10 minutes onto your trip.
I'm not sure what activities you're looking for for the kids, but all of the mentioned towns have beaches and are close to malls (actually, Madison is close to the outlets - you have to drive a bit for big box Wal-Mart, Best Buy style shopping).
You should visit all towns and see which one would fit you best. If you don't mind spending 150% more to live in Fairfield County, that will be for you and your family to decide. I would also recommend you check out Guilford and maybe even Branford. Don't forget to spend some time in each downtown area to get a feel for 'the way of the town'.
While you're visiting, if you have time, take a trip on the Thimble Island Ferry to check out the Thimble Islands. They are absolutely stunning.
Last edited by kidyankee764; 07-15-2012 at 04:52 PM..
Kid pretty much summed it up. I also wouldn't count out Branford and Guilford in your searches, and would consider Woodbridge if you don't mind being in the woods a bit. Also coastal Milford as a dark horse candidate. Particularly the Gulf Street/Morningside/Woodmont area, which tends to have the most homes in the $1.5-2.5MM range. Branford and Milford only suffer in the sense that their schools aren't as highly ranked, but you mentioned before wanting a "normal", non-snobby atmosphere for your kids, and hey, they're both very friendly and down-to-earth towns. One thing I like about both towns is they both feel like "fun" places for kids to grow up, notably near the coastal areas. Anecdotally from people I know, there's no reason to believe they don't offer a quality education. And they have beautiful coastlines (Milford offering an abundance of sandy beaches and Branford rocky and dotted with islands). I happen to think the Stony Creek area of Branford and the Woodmont area of Milford rank among the most beautiful coastlines in the state. Other posters here have an elitist chip and will undoubtedly poo-poo both (just wait for it) for being too middle class for your budget (that didn't stop Dan Patrick or John Ratzenburger from setting up shop there), but it's not like you're coming from an extravagant area and they're worth at least a peek as you advance up the coastline.
Southport and Madison are easily two of the most gorgeous towns in the state. Southport feels more stately, with its protected harbor overlooking a golf course, with 19th century colonial mansions. Madison is more of a sandy, relaxed beach community. The architecture in Madison ranges from more quaint colonial homes, to Nantucket-style coastal mansions. The harbor drive in Southport, and coastal drive along Madison are simply stunning.
If it were my money, it would be Madison above all - however, some people find it too isolated from malls and big box shopping (but who cares when you're 20 minutes from CT's best city?).
I agree, Stylo. Milford is absolutely a "fun" place to grow up, as there is a lot to do, it's safe, schools are good and coastline beautiful. If the OP doesn't mind living in a middle class area like Milford or Branford (you have everything from tiny, cruddy apartments to massive waterfront estates), then they're perfect. It does seem like the OP is looking for a uniformly affluent community, though.
With regards to Madison being isolated from malls - there are two large outlet centers within a 15 minute drive from Madison. The only thing really missing is your big box Targets, Walmarts, Best Buys, and the anchor stores like Macys, Nordstrom and JC Penney. But they aren't too far down 95.
Stop by Seven Seas in Milford for one of the best lobster rolls in the state.
Last edited by kidyankee764; 07-15-2012 at 06:38 PM..
The only thing I could add to these excellent posts is that Southport does have it's own train station, a couple of really good restaurants, and it was the home of a true Hollywood star: Bette Davis.
Southport IS Fairfield and if private schools are interesting to you, the excellent Greens Farms Academy is within 5 minutes of Southport in the Greens Farms section of Westport.
If you're looking for lunch while visting Southport, try Centro in Fairfield Center. It's been one of my favorites for over 20 years.
With the four towns you've named, you're choosing between different versions of ideal living. The "right answer" depends on your priorities. Keep in mind that Fairfield County is quite a bit different in mentality than east of New Haven. Just to give one example, much of FFC is NYC-centric, and you won't find that attitude pervasive or even common in Madison. Many of the shoreline towns have their own sense of place in history, apart from that of Manhattan. Connecticut has its own identity, and sometimes FFC doesn't quite embrace that.
I would not call Southport beachy. It is an upscale seaside village that looks too perfect to be true. Lots of very well maintained large historic homes. I do not remember Betty Davis living there but I know Jason Robards did. So did New York radio personality Don Imus and football great Joe Namath. Also Michael Wetherly (DiNozo) from NCIS grew up there. His father is the importer of Swiss Army Knives and has a house there overlooking the harbor. Nice to have money. Jay
There is a ton of stuff for kids to do in all the towns on your list and I wouldn't call any of the towns you are looking at touristy. Madison is home to Hammonasset beach which is kind of a local/in state tourist beach destination in the Summer months so it's good that you will be checking the town out during "peak" season. Since you are visiting the Southport section of Fairfield, be sure to check out downtown Fairfield and the beach. Southport is charming, but it's more of a marina feel and I think the beach in town is truly a gem. If you need any dining or activity suggestions just give us a shout. Madison is also a great town and I think could just as easily fit your bill. It's a bit quieter than Fairfield but that might be more to your taste (totally a personal preference thing) and I just drool at the kind of house your budget will afford you there. I don't think Westport is a bad choice either, but it is much more expensive than either Fairfield or Madison and I find the vibe to be a bit more appearance oriented and more tightly wound in general than either of the aforementioned towns. I also don't find the downtown to be as appealing as Fairfield's or Madison's. But that is just my opinion and it could be the perfect fit for you! Fall in love with a town and then find a house to fit your needs. Keep the questions coming, this board (shout out to JayCT especially) was very helpful when I was trying to find the right town a couple of years ago and I hope to return the favor.
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