Greenwich! I should probably bow to you, that's one of the richest areas in the country. I grew up in humble Stratford.
Greenwich isn't
all rich, and we certainly weren't. The area where I lived, Cos Cob, was probably lower middle-class at best, and had a lot of immigrant families. My family lived on the second floor of an old farm house that had been converted into apartments. The place was kind of run-down (as I realized when looking at family photos many years later,) but I never noticed as a kid - it was just a fun place to live. The house was at the crown of a hill which was topped by a stone outcropping (suitable for climbing by young boys), and at the bottom of the hill in the back was a swamp, complete with an island. There was an old stone wall at the bottom of the hill, which ended flush at the top of the wall, with about a three foot drop to the level of the swamp. We had a blast in winter sledding down the hill and shooting out into the air over the frozen swamp, eventually skating across to the far side. The trick was avoiding the spring, where the ice was always thin.
My father was a town police officer, and they were so poorly paid back in those days that he used to moonlight doing security guard duty for some of those rich families. I remember visiting him when he was guarding an empty mansion (I think the estate was being disputed and no one was living there anymore) - the place was awesome (especially to an 8 year old kid.) Think of the mansion in
Dark Shadows.
There was one of those large estates less than a mile from our house. Most of the grounds was covered in woods, and they allowed the public to roam the grounds freely and had even put in some asphalt walkways. We used to ride our bikes into the woods there and play all day. They even had a huge pond, where we could fish and swim.