[Pabster]

My wife and I are have been thinking about a move to Westport for some time, for a lot of reasons. We've looked at a number of houses there, and the houses that we really want seem just out of reach. We like the town, but we're starting to think that it might be just a little too ... fancy, I guess.

Weston was always a non-starter for me since I commute to the city. The commute from Westport is long, but it seemed like an okay tradeoff for moving to a town that we viewed as a better fit for a lot of reasons, other than the extreme wealth. But for the first time we looked at a house in lower Weston and have been talking to some people there about what the town is like. It seems like you don't feel the wealth the way you do in Westport, we can get a lot more for our money there, and that it's a community we might feel a little more comfortable in. So we're wondering if this can be a legitimate option for us, and we have questions. Any help on this would be greatly appreciated.

-Are we correct that Weston is a bit more down to earth than Westport, knowing that everything in Fairfield County is relative when using terms like "down to earth"?
-Do people in Weston generally spend a lot of time in Westport? Do people in Weston, particularly lower Weston, basically think of downtown Westport as their downtown since there's not much of a town in Weston?
-Are there a lot of community and athletic activities that include both towns?
-Do a lot of people in Weston commute to the city? Have they managed to retain their sanity?
-Where we are right now is a really strong athletic-focused culture. Is that something we would find less of in both Westport and Weston? Are the towns different in that sense?
-Any recommendations for things we can do in Weston to get a better feel for the town and what it's like?

There are probably more questions, but I'll leave it at that for now. Thanks for any insight you have.

[JayCT]

Weston is a very small quiet town. People there do go to adjacent towns for shopping and entertainment. There are sports in town and a few family activities but not as much as Westport. I am wondering if you would be better off looking in Fairfield. It is larger than Weston, has everything you are looking for and is less expensive and more down to earth. Plus Fairfield has three train stations to get you into Manhattan. Jay

[Stylo]

Weston is more reserved by nature. I don't know about more down to earth. Maybe a little bit.

If you are going to commute to the city, you might want to consider Wilton or Fairfield. Wilton getting you a bit closer than Weston, but similar character and pricing (a bit more commercial than Weston, but still has rural feeling areas). Fairfield, as Jay mentioned, has 3 train stations. If you're in Weston you're stuck with driving a good 15 minutes to get to a train station in some cases. They are both less wealthy than Westport, but still pretty high income areas.

Fairfield is easily the most diverse economically.

[JayCT]

I agree Wilton may be a good choice as well. Jay

[Raider111]

Around here weston is pretty much known as an extension of westport, away from the more congested coastal area, they are virtually identical, not sure you would notice any difference in down to earthiness. Westport definitely has a stronger athletic culture, particularly in football and baseball. I believe the high schools are combined for hockey. I believe also weston has access to some Westport amenities like compo beach and marinas.

[Mike 75]

Everyone I know in Weston describes where they live " as right by the Westport border." Its become somewhat of a running joke with my wife, as no one seems to admit to residing in the northern part of town. That said, I think this speaks to the draw that many people in Weston feel for Westport. Weston They share a Y and Weston residents get the use of Westport beaches and parks. There is also a connection with Wilton as the closest shopping centers are generally in Wilton.

[Danny K]

Well both towns seem kind of ritzy to me, but I would choose Westport because of the coast.

If I understood your post right, you mentioned that you were commuting to NYC, in that case, I would live in Westchester County, NY rather than CT. Look at Rye, Port Chester, and Tarrytown.

[TripleEight]

I live in northern Weston and for many years I commuted to Midtown Manhattan. At 6 am it took me 15-16 minutes to drive to the Westport train station. So living in Weston might add a few minutes (maybe 5 each way) to your commute. If you drive, I don't think there's much difference at all, since you would likely take the Merritt and exits 41 and 42 are equidistant from most points in Westport and Weston. One thing that people often don't realize is that traffic moves at a steady 35-40 mph on the main routes through Weston. There are very few lights and no congestion, so even if you're say, 4 miles from the Merritt, you'll get there in 6-7 minutes.

Regarding wealth. You should know that Weston is a wealthier town than Westport (based on median income), but you wouldn't know it from the people living there. There is definitely a much more down-to-earth atmosphere in Weston.

If it is 'action" you're after I guess you would have to drive for a few minutes but at least you wouldn't be sitting in congestion on the Post road.

Westonites look not just to Westport but also Wilton, Fairfield and Georgetown for services, depending on where you live. In northern Weston, you would likely be only a few minutes from Caraluzzi's in Georgetown, which is widely regarded as one of the best supermarkets in Connecticu

[rubygreta]

Weston is a great place to live if you don't mind driving 15 minutes (or more) on dark winding roads to pick up milk.

It is beyond my comprehension that the town could never figure out where to set aside a couple of parcels for commercial development. Nothing major. You know, a pizza place, dry cleaner, small supermarket, coffee shop, etc.

However, it is a pretty gorgeous place.

[Stylo]

Originally Posted by rubygreta

Weston is a great place to live if you don't mind driving 15 minutes (or more) on dark winding roads to pick up milk.

It is beyond my comprehension that the town could never figure out where to set aside a couple of parcels for commercial development. Nothing major. You know, a pizza place, dry cleaner, small supermarket, coffee shop, etc.

However, it is a pretty gorgeous place.

There are a couple:
Peters Weston Market Weston CT
Weston Shopping Center