Ascot Hill trail is a great trail for your whole family.  The initial incline is very steep but not terribly long for the main portion of the trail, and it is paved to the top. Instead of coming off the other side of the hill, we veered off to the left and met the main trail around the hill's side. At the entrance there are plenty of parking, bathrooms and picnic areas.

Pros:

1. Fantastic downtown views on clear days.

2. Miles of hiking depending on how ambitious you are.

3. You can let your dog off leash without much worry. 

Cons:

1. No shade anywhere in the park really.  In the winter this is not a problem but on a hot summer day I think this is not a good place to come, unless you come very early or later in the evening.  

2. The adjacent neighborhood isn't amazing in terms of other things to do, but you don't have to drive far to find somewhere else to have fun.

https://www.flickr.com/photos/133517056@N05/28207871015