[Updated August 2017 to add summertime pics.]
High Park’s Jamie Bell Adventure Playground is (to my knowledge) the biggest playground structure in the city and certainly one of the best (lots more pics here). Insanely busy in the summer but completely empty (except for us) on this warm November Day. As very young children our kids hated his place when it was swarming with kids in the summer. But they loved it today. They particularly love bouncing up and down on the rubber Bruges (see pic below) especially when dad makes it bounce.
[August 2017 Update: At 5 and 3.5 years old they loved it on a busy summer day.]
The playground is close to the small High Park zoo and bathrooms. It’s a 15 minute drive from downtown with no traffic. As you can see below, it’s a pretty long 21 minute walk from the High Park subway (downhill there – a long uphill walk back to the subway). You can take the park train for $2 a person each way to save a lot of walking.
For toddlers and preschoolers, in the off season, I can’t recommend it enough.
Its located on the east side of the park (see map below). Year round you can almost always find a place to park for free on Parkside Drive near the East entrance to High Park at High Park Blvd. It’s a 7 to 8 minute walk from there.