The wise Sheryl Crow once told us “every day is a winding road,” and while she wasn’t talking about Pittsburgh, honestly, she could have been. That's the typical driving experience when you venture off the obvious routes like the Parkway, 28, and 279. You frequently find yourself on curvy streetscapes that twist and turn, ascend and plummet, like a roller coaster, and some of them are faster and much more enjoyable than the straight shot your navigation app is likely suggesting.
To that end, here are some of Pittsburgh City Paper’s favorite alternate routes that will take you off the beaten path and onto the (usually more scenic) road less traveled.
Flying to the airport
If you’re about to submit to the cramped and clammy conditions of modern air travel, why extend the misery beforehand by holing up in your car, waiting for traffic to inch along the Parkway West? Especially when you could be rolling along the scenic, rush hour-immune back roads and enjoying a smidge of justified schadenfreude.
Starting from the Fort Pitt Bridge, veer right onto Route 51 North instead of heading through the tunnels. Stay on 51 as it ushers you through the shaggy remnants of downtown McKees Rocks, then follow Chartiers Avenue all the way up the hill to Kennedy, where you can join Clever Road heading west. Enjoy the ride as Clever momentarily transports you out of the suburbs and into the rolling woodlands of Western Pennsylvania before spitting you back out on Montour Run Road at the edge of Robinson’s sprawling retail center.
From here, rejoin I-376 West and continue as you would for the final stretch to Pittsburgh International Airport. Take this route during peak traffic times and you’re bound to shave off a few minutes. If the interstate’s clear, take this route anyway, if you prefer trees and rivers to asphalt and aluminum.
Bonus: This route also works to access the Mall at Robinson, Ikea, Costco and the surrounding retail outlets. Just take a left onto Costco Drive from Montour Run right before the turn for the interstate. - Jamie Wiggan
Where the streets have no (consistent) name
Skip the most commercial stretch of Liberty Avenue by taking Sassafras Street, a backroad skirting the southern edge of Bloomfield with the amusing Pittsburgh quality of being a contiguous street whose name changes several times while you drive on uninterrupted.
This unique road has a real middle-of-nowhere vibe for an urban street, taking you where few roads go — both parallel to the East Busway and under the Bloomfield Bridge. It may be worth trying for the novelty, alone.
Heading east, Sassafras eventually turns into Neville Street, and then Lorigan Street, which spits you out at the dead-ends of some of Bloomfield’s one-way streets. Turn left on Cedarville Street if you plan to cross Liberty and keep north to Friendship Avenue, or you can turn left onto State Way if you just need to get back to Liberty. Lorigan Street doesn’t offer access to any destinations south of Bloomfield, however, so it’s best used for lateral East End travel. - Jordana Rosenfeld
Get your kicks on PA-837
PA-837 — specifically the parts of the road east of Carson Street, which, itself, is also part of the state road — offers an enjoyable and usually not-too-congested ride through some of the physical remnants of Pittsburgh’s industrial past.
The highway begins (or ends, depending on your perspective) under the West End Bridge and runs through the South Side, then flanks the southern bank of the Monongahela River all the way through to the road’s southern terminus in Washington County.
Besides the loveliness of having the Mon accompany you on your drive, going south on 837 will take you through several Mon Valley communities that are simultaneously rusty and richly green, and severely underappreciated by city-dwellers who refuse to venture out. - JR
The Allegheny River Boulevard hack
If you’re one of the unlucky Pittsburghers who, at least in theory, has to take the Parkway through the Squirrel Hill tunnels at peak traffic hours, then this shortcut is for you. (Well, let’s be honest, even at off-peak times that tunnel is a messy bitch who loves chaos, so avoiding her any time of day is never a bad call.)
Instead, there’s a detour that takes drivers to the eastern suburbs, and to the Monroeville Mall and surrounding shopping destinations with a lot less aggravation. Simply take Allegheny River Boulevard and turn right on Sandy Creek Road. Stay on this route until it eventually becomes Beulah Road. It will wind you to an intersection where you can turn left onto 376 heading east toward Monroeville, probably wearing a smirk on your face because you’re smarter than everyone else around you. - Amanda Waltz
The Bigelow the better
Pittsburgh may be the City of Bridges, but that doesn’t mean those of us who live here want to cross them for what feels like just the hell of it. Someone please tell that to Waze and Google Maps, which will not infrequently instruct you to cross a river only to have to cross it back to get where you’re going. Case in point: If you’re headed from the northern part of the East End to downtown, the South Side, or pretty much anywhere due southwest, crossing the Allegheny to Route 28 is always the navigation app’s preferred path. Screw that. Bigelow Boulevard is the better way.
Bigelow generally isn’t considered a scenic route, but if you drive it wearing your rose-colored sunglasses, you can appreciate the beauty it contains. While zooming towards Downtown, you find yourself at eye-level with the U.S. Steel Tower, and as you descend towards it, you can catch a few stunning vistas, especially over Polish Hill and the Strip, with just a few quick glances to your right.
In some cases, Bigelow is not, in fact, a shortcut. Taking the Parkway or 28 might actually be speedier, depending on where you’re ultimately headed. But they won’t serve you the same stellar views of our town’s unique topography that are so unmistakably Pittsburgh, and that alone makes it worth the drive. - Ali Trachta
