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You can enter Schenley Park at 40.42921°N and -79.93751°W via Pocusset Street if you like. I entered the park at the Bridle Trailhead at 40.43272°N and -79.93770°W just off Overlook Drive. This trail is very well established and quite popular. The problem with this trail is its close proximity to the Penn-Lincoln Parkway. It’s actually running mostly parallel with this major roadway for quite some distance and it is extremely noisy. This trail actually connects with the Zig Zag Trail at 40.43033°N and -79.94808°W. I followed the Bridle Trail until the split at the Boulevard of the Allies at 40.43399°N and -79.94805°W.
The Upper Panther Hollow Trail picks up at this point and goes under the Charles Anderson Memorial Bridge. The trailhead is just across from the Anderson Playground. I followed that Upper Trail until the intersection with the Lower Panther Hollow Trail at 40.43355°N and -79.93653°W. The park can be entered from here as well at the trailhead just past the Bartlett Playground.
I followed the Lower Panther Hollow Trail past the Tufa Bridge at 40.43400°N and -79.93564°W and stayed on this trail back to Panther Hollow Lake. The Lower Panther Hollow Trail connects to the Steve Faloon Memorial Trail at 40.43445°N and -79.93628°W and the Hollow Run Trail at 40.43443°N and -79.93638°W. There is also a trail connection with the Hollow Run Trail at 40.43582°N and -79.94308°W.
There are several small bridges along the Lower Panther Hollow Trail that crosses small streams filled by small waterfalls. I exited the Lower Panther Hollow Trail at 40.43806°N and -79.94609°W and walked along the Hollow Run Trail. I walked around Panther Hollow Lake but crossed the railroad tracks at 40.43627°N and -79.94956°W. From here I picked up the Junction Hollow Trail at 40.43556°N and -79.94992°W and walked past the Schenley Park Soccer Field.
Junction Hollow Trail ends on Boundary Street at 40.42914°N and -79.94958°W but a few steps along to your left you should notice a narrow gravel pathway leading uphill through the forest. This is, in my humble opinion, the most interesting trail in the entire park. The Zig Zag Trail earned its name! It is also a very steep and in some places extremely narrow uphill trek. It actually winds its way above the Schenley Park Soccer Field and the Railroad tracks and re-connects with the Bridle Trail at 40.43033°N and -79.94808°W. It is not as popular as the other trails in the park so it’s a great chance to really enjoy the natural landscape without the annoyance of others constantly around you. If you don’t do any of the trails in Schenley Park you have to do just this one!
I continued along the Bridle Trail and took the tunnel at 40.43493°N and -79.94722°W going under the Boulevard of the Allies. This goes past the Schenley Swimming Pool and the Anderson Playground. I re-entered the Upper Trail at 40.43576°N and -79.94857°W and took the flight of stairs at 40.43624°N and -79.94733°W down to the Hollow Run Trail. I continued along this trail from the trailhead at 40.43693°N and -79.94684°W. This trail starts out wide but gradually becomes very narrow and muddy when it nears Panther Hollow Run. There are many people walking dogs along the trail as well so it’s interesting navigating around very narrow sections. Apart from the dogs the Hollow Run Trail is the second most interesting trail within this park.
I exited the Hollow Run Trail at 40.43443°N and -79.93638°W onto the Lower Panther Hollow Trail and then started the Steve Faloon Memorial Trail at 40.43445°N and -79.93628°W. This trail skirts along the East Circuit Road above all the other trails in the park. There are a couple of exits from this trail onto East Circuit Road. I followed on past the Westinghouse Shelter at 40.43816°N and -79.94435°W and exited on West Circuit Road at the marked trailhead at 40.43873°N and -79.94372°W. I took West Circuit Road to the Westinghouse Memorial at 40.43943°N and -79.94272°W and then crossed Schenley Drive at 40.44019°N and -79.94248°W. There is an entrance there just past Tech Street at Carnegie Mellon University to get to Flagstaff Hill. There are good views of the Oakland Area of Pittsburgh from this area. It’s very crowded with mostly university students on sunny days though.
I crossed Schenley Drive after exiting Flagstaff Hill and continued along Panther Hollow Road past the historic Panther Hollow Bridge at 40.43740°N and -79.94691°W. I followed this road right back to the main intersection at 40.43286°N and -79.93652°W with Greenfield Road, Panther Hollow Road, Bartlett Street and Hobart Street. From here it’s just to walk back to the starting point of the trek.