This was my favorite type of run – start with friends and then grab some new streets on the way back. Actually, my FAVORITE run would have been to have all these folks come with me, but a 300′ hill is a hard sell.
It was a cool, humid and cloudy morning. Temps held steady in the low 40’s with intermittent drizzle. We started at Ascend, nestled as it is between old multi-story brick buildings. We made our way to the Liberty Bridge, accessing the sidewalk via a muddy walk-way under the bridge and a short set of stairs to the deck. Once on the deck, the downtown skyline spread out before us.
Brew House Building outside Ascend 
Downtown from the Liberty Bridge
Once in downtown, we zigged and zagged toward a water stop near the Wyndham. This was three miles in. The planned route took the group in a cloverleaf around downtown, coming back to this water stop several times. I decided to branch out on my own. I had various choices – explore more of Brighton Heights; criss-cross my way through Manchester; climb Greenleaf onto Mount Washington. Eventually, I decided on Greenleaf, in part because it was going to be closed for construction soon. After some tearful goodbyes (just kidding, a couple of people waved bye), I started out.
Downtown from West End Bridge 
Looking Up the Ohio River
Now getting to Greenleaf is not straightforward. It is a small residential street which falls off of Mt. Washington into the West End Circle. To get to the West End Circle, I had to cross the West End Bridge and find my way to the other side of the Circle. The West End Bridge has approach ramps and stairs for pedestrians. The pedestrian ramps are notoriously flexible and you can feel it bucking up and down when a group runs across.
After crossing the bridge, I was able to cut across the circle, passing the end of Sawmill Run (notorious for flooding). Finally, I got to the base of Greenleaf Street.
Bouncy Bridge 
Sawmill Run 
Base of Greenleaf
From here it was up. On one hand there’s no sidewalks, on the other hand, there’s not much traffic. Even though you’re supposed to run facing traffic, on hills like this, I find running on the uphill side better. Cars aren’t going to be zipping by. Pretty quickly, Greenleaf climbed high enough to start showing off views.
Looking down Greenleaf towards West End Bridge 
West End Neighborhood
At the top, Greenleaf wraps around into the modest residential neighborhood of Duquesne Heights. George and Guy Trail hugs the cliff below Skookum Field, where a baseball hit 190′ would tumble far down the cliff.
Crazy Trail 
Home Run Distance
The views are spectacular and several snazzy houses vie for space along the cliff with the WBZZ radio tower. Small lanes between the newer houses had the best security. I felt watched.
Ent Vision 
View from WBZZ
Greenleaf Street continued through Duquesne Heights. This is an interesting area. Tall narrow houses are literally under large view-hogging condos. Street stairs and connecting stairs abounded. Greenleaf Street transformed into a stairway before transforming again into an alley. Sioux Way was part-stair, part brick.
Finally, I made my way to Grandview Avenue, that popular promenade overlooking Pittsburgh. At the eastern end of Grandview, Vinecliff Street, a weathered set of stairs and asphalt, struggles down the hill. I took that en route to finishing back at Ascend.
