If you're considering perhaps exploring Pittsburgh on a bike, the most helpful thing to understand is that the city has a split personality, a real schizophrenia when it comes to cycling. I found it to have some completely awesome places to ride a bike; other parts of the city offered some of the most challenging experiences I've encountered.
Here's the deal. Pittsburgh is built where the Allegheny River and Monongahela River come together to form the Ohio River. The space between the Allegheny and the Monongahela is known as the "Golden Triangle." The heart of the city lies here on this ancient floodplain, including its downtown area and it's very flat and a sweet place to ride a bike. However, much of the rest of the city is perched on the steep hillsides that circle this area, and these great many hills are the counterbalance to the joy of riding in the area radiating out from the rivers' confluence.
For the first-time visitor or neophyte Pittsburgh cyclist, the place to start is at Point State Park, which sits where the rivers come together. There you'll find fountains, broad walkways and spectacular views of the city. A whole network of bike paths go out from there along the region's three major rivers. You can easily ride to a number of fun and interesting destinations, including Heinz Field and PNC Park which site on the opposite bank and serve as home to two of Pittsburgh's professional sports franchises, the Steelers (football) and Pirates (baseball), respectively.
For rental bikes, advice or just basic necessities like spare tubes, snacks and drinks, you'll want to go to Golden Triangle Bike Rental, located just a few blocks southeast of the Point at 600 First Avenue, Pittsburgh, PA 15219 right on the Three Rivers Heritage Trail. Golden Point Bike Rentals also serves as an outfitter for cyclists wanting to take on the Great Allegheny Passage, which along with the C&O Canal towpath trail, offers a traffic-free, 340-mile ride from Pittsburgh to Washington, D.C. You can call 412-600-0675 for more information, either to arrange for local bike rentals or to find out more on their top notch bike tour planning services.
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In an effort to enhance and promote cycling, Pittsburgh has taken full advantage of both the scenery and topography of these areas along the river. Over 24 miles of paved, traffic-free trails follow the riverbanks, and numerous bridges that are friendly to both bikes and pedestrians allow for easy access to paths on either side. I would strongly recommend these as the right choice for people just starting out, either with their visit to the city and/or their experience on a bike. Because they follow the path of the rivers, these biking and walking paths are in general going to be very flat and therefore fun and easy to ride. The Three Rivers Heritage Trail is the catch-all name for the trails on either side of the three rivers; you can find a great map of the Three Rivers Heritage Trail here.
Though the city has established a collection of color-coded signs to make getting around easier by identifying general neighborhoods and specific destinations within them, I still found biking in Pittsburgh to be challenging outside the flat central city and bike paths along the rivers, both physically and navigationally. Streets in these neighborhoods are narrow, steep and windy. The houses are charming, sure, and there is a lot of history to be found but you have to like climbing a lot to enjoy riding these. Another major downside is that the extraordinarily steep hillsides mean that fast traffic from these neighborhoods is often funneled into just a few narrow arterial roads without much shoulder; these roads are not much fun at all.
Summary: While Pittsburgh is a beautiful city with its high hills ringing the confluence of the rivers, the steep winding streets can be a challenge to ride. Most all cyclists, and in particular visitors to Pittsburgh as well as locals with less experience on a bike will find the most enjoyment if their riding is mostly done on the city's well-planned, well-maintained network of trails that follow the banks of the rivers right in the heart of the city. The paths are flat and take riders past some of the city's best attractions.