Try the Roller Coaster -- to find the trailhead, enter at the Beechwood Blvd entrance in Squirrel Hill and go until the trail turns from paved to gravel.
How to get there:
The best entrance is at the at the Beechwood Blvd entrance in Squirrel Hill. If you're on Forbes Ave coming from Oakland, pass through the intersection with Shady Ave, turn left on Beechwood Blvd and wind down a few turns. You're looking for an entrance to Frick Park on your left near a children's playground.