I'd go Squaw Run up over the hill towards Hartwood, and through the park to Middle Rd. Middle to Wildwood right into North Park. My folks live out there, that's how I tend to make the ride their direction.
If you're feeling adventurous and want to get some trail miles in you can pick up the Rachel Carson trail at McCully Rd near the Middle Rd intersection, which you can then follow the entire way into North Park. Just follow the yellow trail blazes on the trees.