ShonTron
Moderator
I think it's just to protect the park. Pine Valley and Leslie are interrupted for the same reason.
No, Kipling was never really a through route north of Steeles. The road allowance was likely abandoned as a through route decades ago - Islington Avenue was nearby and Steeles wasn't continuous either until the 1970s. A tributary of the East Humber River runs through there.
And yes, there's an old dump north of the Steeles/Kipling intersection that was used in the 1960s. There's also the CN York Sub, built in the early 1960s (and of course, the 407).
Pine Valley is a concession line, similar to Islington to the south. But Islington leaves the grid to serve Woodbridge (it's a very old route) just south of Steeles and Pine Valley shifts east to meet Fermar because of the CP MacTier Sub.