On the Monongahela River, the trail goes five miles (8 km) upriver from Station Square to a point just short of the Waterfront Shopping District.

Some people call this section the 'Jail Trail' because it also passes the Allegheny County Jail on its way to Oakland, the university center of the city.

Pittsburgh is one terminus of the 335-mile (539 km) long 'Great Allegheny Passage' (GAP)[4] that connects the city to Cumberland, Maryland and Washington, D.C.

For many years, the trail hosted the annual 'Pittsburgh Triathlon',[6] a competition for top athletes who use the land and water routes to bike, run, and swim for this Olympic qualifier.

A less demanding version is the 'Adventure Race',[7] for friends, families, and teams who wish to paddle, bike, and run a shorter yet challenging course.