I'm considerably older than you OP, but this isn't a description of my childhood.
From aged 8 I could ride wherever on my bike all over town
We had limits where we could go "round the block" or to limits - or to a specific park which my parents knew we were going to.
Exactly the same rules for my dc
we had the most imaginative play, we kept up for the whole six weeks holidays that the mills behind us was haunted, I convinced a peer to trap a bee in a jar to save my life - we all knew it wasn’t true but played along as it was all part of the story, and ate a mud pie after sacrificing the bee
I'm pretty confident my dc have done similar (no mills specifically)
I was allowed out to play from when my parents left for work until tea, and then from there until it got dark
Well that is just damned neglectful, and I am very surprised you were doing that in the mid 90s. It certainly was never the norm.
we had secret woods, haunted woods, various (unsafe) rope swings and biking routes
As have my dc
In comparison DS8 gets to go on “play dates” and prearranged activities
Well, why are you limiting your dc if you feel it is so bad ? 
AIBU to grieve for the good times being a child
Not unreasonable to look back through rose tinted glasses and mourn for the days when you were carefree
.....and wonder why we are so closed off with our children
well, I'm not. Nor are lots of parents.