The Old Squaw Trail, located just outside of Pittsburgh in Fox Chapel, Pennsylvania is a relatively easy 6.6 mile out-and-back hike that starts at Beechwood Farms Nature Reserve and heads south along Squaw Run creek.
Starting from Beechwood Farms, the trail passes a dog park before heading downhill along Squaw Run through the power lines heading south. The trail itself has green blazes (scarce) on trees, but they're mainly on small sign posts - about knee high.
The trail cuts through Riding Meadow Park, Scott Park, and finally McCahill Park before ending at the intersection of Guyasuta Road and Squaw Run Road in Fox Chapel. Riding Meadow Park, Scott Park, and the initial dog park in the north near Beechwood Farms all allow unleashed dogs; however, you must re-leash upon exiting the parks back to the trail itself.
Upon exiting Scott Park, the trail heads south along Squaw Run Road before entering McCahill Park and continues along the road until you reach Guyasuta Road. The trail is mostly flat from the beginning of Scott Park all the way to Guyasuta Road.
Note: The trail crosses the street several times - be on the lookout for brown signs that say "Trail" with an arrow.
Parking: Park at the Beechwood Farms Nature Reserve lot and cross the street to the trailhead. Additionally, you can park at the southern trailhead at McCahill park along Squaw Run Road or at Scott Park. Riding Meadows Park is permit-only parking, so beware before you park there.
Difficulty: The Old Squaw Trail is not too difficult, especially heading south, since you're mostly hiking downhill; however, there are various ascends while hiking south. Hiking back north is more challenging, but isn't any worse than easy-to-moderate.
Waterfalls: There are several tiny waterfalls along this trail, but the best of them run in the Spring. Within about 0.5 to 0.7 miles into the hike, you'll cross Squaw Run with an 8 to 10 foot rock ledge with a creek that trickles off of it - in the spring, the rock ledge acts as a waterfall. Just behind it is another small waterfall about a foot and a half tall, so nothing special. Further into the hike, there's a man-made waterfall about 2 feet high which is just runoff from a reservoir - this one is located about 1.5 to 2 miles into the hike.
Old oil well: Along the trail, at about 0.4 miles in from the northern terminus, is an old rusty oil well sitting along the right-hand side of the trail while heading south or left-hand side while heading north. This is a unique piece of western Pennsylvania's history rusting away in the woods.