Given that I live in N. Oakland, this trail is my gateway to the Three Rivers Heritage Trail…read moreSystem, a.k.a. the bike trails that run along all of Pittsburgh's rivers. It cuts through Schenley Park in pretty much the straightest and least hilly manner possible, connecting Oakland and Greenfield.
The only part of this trail that I don't particularly like is the Greenfield end, where it loops around through part of the neighborhood, under the railroad bridge, and up into the trailhead parking lot for the Eliza Furnace trail. While it may be the safest way to get through this neighborhood at present, I particularly dislike the narrow blind corners, so on my way up to the trail, I often avoid them by climbing the hill and crossing the RR tracks (which you're not supposed to do, but I'm a railfan, so I know about trains and I'm careful). Speaking of which, closer to the Oakland side, this trail connects to the other Schenley Park trails via a connector that crosses the RR tracks. While not nearly as busy as many other RR tracks in PGH, these tracks (the same ones I cross) see a few trains a day, so take appropriate caution when crossing them.
I've heard that wild turkeys live along this trail, but I've never actually seen them--at least, not in the park. (I did see them near Central Catholic HS one time). If you do encounter them, be careful, as they are hostile to cyclists and may attack!