As many of my readers are dirty biketivist hippitarians, I have constructed this little urban cycle tour of Pittsburgh, to entice younz all to our fair city. It hits a decent cross-section of city neighborhoods, although skips those where you can score good dope, the West End neighborhoods because who cares, and the North Side because Danger Will Robinson.
Beginning Downtown in the theater district at Seventh St. and Penn Ave., head East Northeast on Penn, cut left at 11th St. and right again on Smallman, which you will follow all the way through the warehouse-y back end of the Strip District, looking out for potholes, semis, and railroad tracks. At 32nd St. in Lower Lawrenceville you'll turn right, go a block, and then left onto Penn, following it up the hill to Main St., at the border of Lawrenceville and Bloomfield. Take a right on Main and then a left where Main hits Liberty Ave. Liberty runs all the way through the heart of Bloomfield. Watch out for drunks, motorcycles, and drunks on motorcycles. Liberty becomes S. Aiken Ave at Center Ave, and you'll stay on it, heading into Shadyside. At Walnut St. turn left and keep an eye out for suburbanites trying to parallel park Suburbans. Walnut runs through the Shadyside shopping district and a little cross-section of the Shadyside residential scene. At Shady Ave., turn right, and head uphill, crossing 5th Avenue, and keeping your eyes peeled for Pittsburgh's few Messicins, tending lawns of petite bourgeoisie estates.
At the top of the Shady Ave. hill, turn left onto Wilkins and head downhill. At the light at the bottom of the hill, bear left onto Dallas Ave. At the light, turn right onto Reynolds St., Pt. Breeze's and maybe Pittsburgh's prettiest residential street. Take Reynolds past the Frick Art and Historical Center and the entrance to Frick Park on your right, watching for unleashed dogs, then turn left on Lexington and head down to Penn Ave. At Penn turn right and proceed to the corner of Penn and Braddock Ave. This is a traffic-heavy stretch. Watchout! You'll follow Braddock until you come to the light at the intersection of Braddock and Forbes Ave, with the Frick Park Playground just in front of you. Turn right on Forbes, which is another busy and fast-moving road along its lower half.
Forbes cuts through Frick Park and then heads uphill to Squirrel Hill. You will go through one end of the Sq. Hill business district and then a bit of residential until the road dips downhill and curves right. Here you will instead bear left, watching oncoming traffic, and head into Schenley Park. An immediate left on Darlington Road followed by a quick right onto Circuit Road will send you down a fun, curving hill with a couple of nice switchbacks. It will dump you onto Schenley Drive. Hang a left and then follow it as it curves right, crosses Panther Hollow on a bridge, and brings you around behind the Carnegie Museums and Library. Follow the road around the Museum and hang a right where it dead-ends into Forbes, aiming for the left lanes, which are turning lanes. At the light turn left onto Bellefield, and then make a quick right onto Filmore. Filmore crosses the busy little commercial Craig St and sends you down a short steep hill to Boundary St, which runs through Panther Hollow. Watch for wild turkeys. For real. Follow the bike trail signs, as Boundary turns into a bike and walking trail that takes you under the Parkway and into the Cut. From there, follow the signs for the Eliza Furnace Trail (AKA the Jail Trail). Take the trail until you see the ramps, which take you up to the bike lane of the Hot Metal Bridge. Cross the bridge and you'll find yourself on the South Side. Hang a Right on Carson St. and follow Carson all the way through the busy South Side bar district, watching for drunks, homeless people, gutter/crust punks and their dogs, and suburbanites. At Station Square, turn right and cross the Smithfield Street Bridge, heading back into downtown.
Follow Smithfield St. all the way across town to Liberty. Make a left and then immediately right onto 9th Street. 9th takes you over the Allegheny River to the North Side. Hang a right and then bear right onto River Avenue, which runs all the way along the Allegheny River to 31st St. Turn right and cross the supremely goofy 31st St. Bridge. At the light, turn right onto Penn Avenue, and then follow Penn back through the main drag of the Strip District until you end up back Downtown.
23 miles and a fair portion of the city.