From Ron Edwards: 

Laurel Highland Trail
First 8 miles starting at Ohiopyle – steepest/hilliest section. Also the last section of trail (near the 70 mi end) is hilly. Close enough that you can go early in the morning and still have a good chunk of the day left. Comments: excellent training on steep trail.

Rachel Carson Trail
Trail with variety of terrain: single-track, double, wide right of ways and power line cuts, and road. The first 12 miles from North Park are fairly easy.

The hilliest section is called the “Roller Coaster”. It starts in Springdale (at about the 1/2 way point) and goes North toward North Park to about the 12.5 mile mark. There are also plenty of hills as you leave Cheswick and head NE on the trail. In general between miles 12.5 and 26 are the most challenging.

This trail is probably second best training option after the beginning and end sections of the Laurel Highlands Trail.

North Park Perimeter Trail
The toughest in North Park. It is at least 10 miles and is all hills.
Trailhead: (need info)
Trail Description: (need info)

North Park Hiking Trail
Trailhead: Follow signs to Swimming pool then to Pie Traynor Field. You'll see a trail map by the field.

Trail: Follow the Pink blazes to the left (back toward the pool). A few places where you can lose the trail. One is where it crosses under Babcock Blvd. follow the stream. The next is by the bike rental shop where it crosses Wildwood road - cross the road (yellow belt). The trail goes up between Kummer Rd and Beauty Dr. Next at the horse arena - go through the area and look for the blazes by the road.

There are a lot of criss-crossing and parallel roads – not a great feeling of being “in the woods”

Frick Park
2 Entrances:

1. Beechwood Avenue – Follow the paved path to the trailheads
2. South Braddock Avenue

Very rough single-track mountain bike trails. Trails are loops. You’d probably want to string together a couple loops for a workout session.

Trailhead: Enter Park trail system at the environmental center off of Beechwood Boulevard or the playgrounds further up Beechwood

Trail Description: Moderately technical singletrack with lots descents. Good singletrack can be found throughout the park. Follow the paved path at the playgrounds off of Beechwood Boulevard back toward the soccer field and watch out for all the dogs. Trailheads to several descents can be found at the far end of the soccer field. Pick any trail and it will lead you downhill. At the very bottom follow the park road to the left and climb back up the Ravine(?) Trail toward the top again. This park may not be the safest place to ride at night.

Riverview Trail: easy

Riverview Ext.: easy/moderate

Fire???:

There are tons of single-track mountain bike trails criss-crossing all over and intersecting with main hiking trails. The single-tracks are hilly and narrow – recommend no headphones as you’ll need to be alert for incoming bikers at all times.

See Frick Park Map document. No trail map exists.

Moraine State Park Trails
Wyggeston Trail: 1.5 to 4.5 miles, moderate hiking. Comments: a couple hundred feet of elevation changes. Fairly simple.

Glacier Ridge Trail: 14 miles, moderate hiking. Comments: Topo map looks like 100-200’ elevation changes - fairly mild.
See Moraine State Park map and Moraine State Park – Hiking Trails documents for further information.

McConnell’s Mill State Park Trails
3 trails. According to topo maps the trails only gain hundred feet or so of elevation changes. Fairly easy hiking.

Hartwood Acres?

Brady's Run Park
single-track hiking and mtn. bike trail, 10.5 mile loop with shorter variations, lots of climbing. Road running is anywhere between Bell Acres Borough and Sewickley. Beautiful, shaded, hilly, little used roads