High Park has a nice leash free area for dogs to run around. It's pretty crowded, especially on summer weekends. There is free parking, which is a bonus, but there never seems to be enough of them. Quite a relaxing place to hang out, can be quite romantical. Lots of walking area and paths. You can go see a play in the summer if that's your thing, or skate in the winter.
Right by the shops on Bloor West, there's a lot of little cute shops in the area, worth to check out. Go down to the water, a short walk away and watch people play volleyball on the beach. There's quite a few things to do in the area, so slot a day or two to check it all out.