If you have a country home in CT (Litchfield County) do you socialize much up there and if so with whom? DH and I are considering a country home but concerned about socialization opportunities for us and later DC. most of our friends have second homes in the Hamptons (which is also an option on the table) but we think maybe we would like the country better - more space, beautiful year round, closer, etc.
In my experience it's good when the kids are young but they get really bored when they are older. I think that a place in Long Island doesn't get you very much for your $ but the kids will always want to go there when they are older too
I have a home in Litchfield County and socialize a lot. It helps to know people who are up there already or to join a local country club. There are lost of options up here and it is a no brainer way of meeting people and having your kids be surrounded by other kids. It is also much more low key in Litchfield County than it is in the Hamptons.
We have a place upstate and we don't really socialize with anyone while we are up here. Maybe one party a month, a couple of pool days. The solitude is the point. If you want a social scene you should probably find a place in town.
OP - we are currently upstate as well and really enjoying the solitude and the outdoors which sparked this idea but I wonder if we would enjoy it long term and would DC enjoy it once he is older and friends become more important. we are not overly social but enjoy occasional dinner when in the city.
We have 3 DCs so no one is ever really alone. I sometimes wish we were close enough to a town to walk or bike in but I also love not being able to see our neighbors. Everyone is a trade off. Space and quiet is much more important to me than having people nearby. The summer set around here is spread out enough that you won't necessarily be around at the same time as your friends.
We rented upstate but need to buy. Any beaches nearby ?
I think the only real way of figuring out what you want is to go visit a few places and arrange to look at homes in your budget. See what you can get, see how the drive feels and ask the realtor about the scene and opportunities to meet people. They are so plugged in to these small communities. I think 'boots on the ground' research is the only way to figure out what you want. You may also be surprised what you like and what is actually a dealbreaker.
You need to buy in a community if you want to be social. That way when your kids are older they already have friends in the country so it will be less of a hassle to get them to go. Look at Lakeridge in Torrington or Woodbridge lake in Goshen.
We ended up buying a house in a suburb about 45 min north of NYC by train or highway. That way if the kids aren't so in to it they can easily stay in NYC and we go out to the house. It's still fairly rural but close enough to other towns that have retail.