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Since I am a little south of the city, most of my favs are in the Monroeville/Greensburg area...but here are a couple of my favs!

1.  Boyce Park, Monroeville-->Nice paved walking paths, well monitered by security and therefore seemingly safe and expansive enough to walk through different portions and not be incessantly bored from the same scenery.

 

2. Twin Lakes Park, outside Greensburg-->Very scenic, family friendly and pet friendly for those of us dragging shih tzus behind us in the urge to be healthy and the park is spectacular in the fall with the leaves and such.  Great area for taking the kids and convincing them that walking/jogging is fun.  Also has great fishing...

 

3. Nature Trail, Greensburg--> Behind that police barracks and municipal buildings near Best Buy.  Very nicely maintained walking areas in a woodsy setting.  The paths are not paved, so after the rain it is a little tough hiking.  The path are about 1-3 mi total depending on the direction you take.  Definitely a trek to take with friends though, because it is not monitored.

 

4. Hempfield Park, Hempfield Twp-->My least favorite for outdoor walking, but it does have a very nice indoor walking track that is free and open to the public.  It definitely beats trudging through the snow and rain outside.  It also have clean bathrooms and water fountains for those discerning walkers that prefer not dealing with portable potties in the outdoor venues!

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Rails to trails bike trail which runs, hmmm...  i think it's in the process of being vamped so that it runs from downtown Pittsburgh all the way to Washington DC.  i like getting on in Boston, PA and riding towards Westmoreland county.  It's really beautiful scenery and the grades are no more than 3%.  There's a very friendly small business that rents bikes in Boston, PA as well.

#2  
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There is a great park called Hartwood Acres up near Fox Chapel. They have a great dog park and paved walk ways. They also have alot of grassy areas for recreation. 

I don't know if anyone has been to White Oak Park but it is really nice too. I live right by there so go there often. They have a dog park as well (fenced). And a main road (not heavy with cars) that is about 3.2 miles the whole length. There are pavillions there for picnics and playgrounds. Nicely upkept and monitored by local police.

#4  
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North Park is a must have on your list. The lake walk/bike trail is 5 miles around and on a nice day very popular.

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