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I used to ride through Crafton to/from Sq. Hill. Most times I'd just take Steuben all the way to the circle. The other route I used (a bit longer, but definitely less traffic and a little less steep) was Ingram->Prospect->Mainsgate->Berry->Straka->Chartiers->Steuben.

I didn't think the circle itself was that bad but taking the ramp onto and making a left off of Carson was easily the worst part of the trip. Walking might not be a bad option, I think there are stairs.

Once you're into the station square parking lots you can get on the trail, I'd take it all the way to Hot Metal, then make a right and go down to the Junction Hollow trail, and from there Boundary->Joncaire (steep climb + cobbles though...)->Bouquet.

If you want to ease into things, you can take a bus from crafton to station square - it definitely cuts out the hilliest and highest traffic part of the route, the rest is mostly on the trail. And, there are a lot of variations (Birmingham Bridge, Bates St., etc) you can try once you're more comfortable with the route.

good luck,

salty essentially nailed it.

gotta get your reps up and conquer the West End Circle, which is easier heading outbound than in. may not be 100% proper etiquette, but cheating up on the lights, taking the front of the line, and asserting your position through any crossovers/intersections seems to work best through there.

the timing of the new signals definitely makes it doable.

The trickiest part is that last 1/2 mi from the end of Main st through the circle to the first entrance drive to Station Square (inbound).

You also might want to try working your way over to Noblestown Rd instead of Steuben, it is really wide, with good shoulder and mostly no parallel parking. Going outbound on Steuben the kink in the road right at the climb is a bear, and cutting through that adjacent neighborhood to miss the kink, I've heard is sketchy.

Yeah, that climb on Steuben is something... I'd sometimes cut through i.e. Chartiers->Lorenz, I wouldn't call it sketchy but Lorenz is really steep too.

One thing I just noticed on the map is Chartiers->Lorenz->Crucible->Woodlow - I wish I had tried that. It looks pretty sedate, not too far out of the way, and might spread out the climb a little.

Look, there's even a dude walking a sheltie there.