In winter we would look for the most dangerous looking hill we could find for sledding.
We lived on the edge of a small town with a farm kitty-corner on a hill across the road. The hill had a large area excavated out of one side that was maybe 100' deep. I had a pair of skis with the old toe/heel straps. We'd take them up to the top of the cliff in winter and ski down into it at speed. Crazy, but was it fun!
We would do that as well, and because the sun went down before 6pm we’d be doing it in the dark. We would also ride our toboggans like a surfboard, decades before the snowboard was invented.
Interesting bit of trivia- the actor Enrico Colantoni (lead alien in Galaxy Quest) broke his leg while toboganning on a hill at the end of my street and was laid up for a few months.