Pittsburgh is a city of hills, breakneck curves, complex intersections and lousy drivers. This usually means a no-go for urban riders.
But the city's biking culture has grown steadily in recent years. There are numerous commercial bike stores and grass-roots repair shops. The city is crisscrossed with paved trails and brand-new bike lanes. Thanks to the local advocacy group, Bike Pittsburgh, urban riders can find safe and efficient routes throughout the city. The hills are still long and steep and the city suffers from a minefield of savage potholes, but for avid city cyclists, there's no better place to cut your teeth.
For beginners, the easiest trails fall along Pittsburgh's Three Rivers. The Eliza Furnace Trail is particularly popular, running from Downtown to Squirrel Hill in a continuous line that bisects several highways. Riders can find access at the bottom of Greenfield Avenue or next to the Courthouse and Allegeny County Jail (this conspicuous starting line has earned the Eliza Furnace the nickname "the Jail Trail").
Another trail traces a line from the South Side Works (a posh shopping development), all the way across South Side (a major shopping and nightlife district) to Station Square (a converted railroad depot packed with shops, restaurants and nightclubs). The South Side and Eliza Furnace trails used to be separate and distinct, but today riders can easily pass from one to the other, thanks to the newly bike-accessible Hot Metal Bridge. This thoroughfare is not only convenient for walkers and bikers; it also offers a breathtaking mid-river view of the city.
Riders may also take the North Side trail from Heinz Field to historic Washington's Landing and beyond. Washington's Landing is a separate island, said to be "discovered" by George Washington (who capsized his raft and nearly drowned there). The trail circumscribes the islet and connects with the newly renovated 31st Street Bridge, which carries riders to the Strip District and Bloomfield.
Riding on the street is where Pittsburgh earns its bad reputation: streets are narrow and confusing, and as the locals say, "Every street is one-way, going the wrong way." Still, as long as riders observe the rules of the road (helmets, clear hand-signals and flashers for night-riding), biking through the city can be a surprisingly pleasant experience. Cruising through South Oakland and Shadyside provides a unique view of their quaint little streets, and riders can usually keep up with slow-moving traffic. The freshly-painted bike-lanes in Bloomfield offers riders safe passage through Pittsburgh's "Little Italy," along Liberty Avenue (with restaurants and pubs galore).
For the safest and most engaging outings, you can find a free Bicycle Route map in most cycling shops, courtesy of Free Ride.
If you're the type of rider to welcome inclines as a personal challenge, Pittsburgh is your city: There are only four main entrances to Polish Hill, and all of them are steep and terrifying. The toughest route is Herron Avenue, which traces an S-curve along Polish Hill's slope, gradually twisting through the neighborhood and ending at Melwood Avenue -- a notoriously crumbled street that leads to Oakland.
For riders seeking an eye-popping panorama, try climbing Mount Washington; this neighborhood rests on a series of cliffs that overlook South Side and Downtown, and it's by far the most romantic view of Pittsburgh. To reach it, turn off Carson Street at Station Square and shift into a low gear -- if you can make it to the top without walking, you're probably ready for Iron Man.
A more relaxed challenge is Squirrel Hill, arguably Western Pennsylvania's most delightful neighborhood. The roads are long but not steep, and once you reach Squirrel Hill, you'll find more ethnic restaurants, delis, ice cream parlors, novelty shops, community centers and sports bars than you'll know what to do with.
Surprise, surprise -- Western Pennsylvania is considered one of the best regions in the U.S. for mountain biking, and you don't even have to leave city limits. Rugged trails have been carved into Schenley Park and Frick Park, two innercity green spaces that feel more like remote forests. Bikers spend entire afternoons exploring these parks, losing themselves in the trees and breezing over wooded ravines.
Pittsburgh's battered streets cause a lot of wear and tear on bicycles, and riders are routinely plagued by flat tires, bent spokes, rain-rusted chains and worn brake-pads. As usual, Pittsburgh is a do-it-yourself kind of town: Riders can find knowledgeable bike mechanics at Iron City Bicycles in Oakland, Kranick's Bike Shop in Garfield, and Free Ride, a bike-recycling and maintenance clinic in Point Breeze. All three locations maintain a "teach a man to fish" philosophy, instructing visitors on how to repair their own vehicles.
Riders will often spot wrought-metal frames, shaped like circular sculptures, sticking out of sidewalks throughout the city. These artistically-renderred bike-locks are designed to represent the Three Rivers and are made possible by a partnership between the City Council and Bike Pittsburgh. Pittsburgh may be a relatively safe city, but riders should be careful lock their bikes (through the front wheel) and take precautions against seat-theft.